Episode 3: Learning

Angie Chang: Welcome to another episode of Girl Geek X Podcast, connecting you to the best in tech from women in tech. I’m Angie, founder of Girl Geek X.

Sukrutha Bhadouria: Hi, I’m Sukrutha, CTO of Girl Geek X.

Gretchen DeKnikker: I’m Gretchen, COO of Girl Geek X.

Rachel Jones: I’m Rachel, the producer of this podcast.

Angie Chang: Today this episode is all about learning. We hear all the time at Girl Geek dinners that women are looking to learn new things, they’re asking how to do that, how to do that best. Do you do it on the job, off the job? To me, learning means narcolepsy. I remember sleeping through every class at Cal, and nowadays I love listening to podcasts while driving in traffic, or listening to a YouTube economics lecture while doing something like washing dishes or cleaning, to make up for the fact I don’t plan on going to business school.

Sukrutha Bhadouria: For me, learning is basically a necessity, no matter how I get it. Because when you’re in tech or you’re an engineer, you are out of date very, very quickly. What about you, Gretchen?

Gretchen DeKnikker: I think I’m one of those read all the books and take classes, especially taking classes, because I like the structure. It helps me not procrastinate. I’m definitely a go-find-those-things-that-way, outside of work, for kind of extended learning.

Rachel Jones: I am definitely a learner for learning’s sake. I just love to take in new information. For things like starting a career as a podcast producer, I’ve had to do a lot of independent learning outside of the workplace. Today we’ll be diving into topics like where learning happens, how to fit learning into your day to day, and how to hack your brain to learn new things.

Sukrutha Bhadouria: How do you know when you need to learn something new?

Angie Chang: I guess this is by necessity, right? When you start seeing the signals from people where you’re like these are the things I need to learn because nobody else is doing them, I think it’s different for people that work in bigger companies because it’s more clear what those things are, or you have a review process that will constantly tell you what you need to improve on. When you’re at a smaller startup, you always have to keep your ears open, and try to hear from your colleagues or customers about what are the shortcomings that you have, so that you can address them.

Gretchen DeKnikker: I find when I’m getting bored at a job that I tend to start taking classes, or start looking at different things. I find that there’s some part of my intellectual stimulation that I need to go get from somewhere else, whether that’s taking a class at City College, or signing up for some crazy workshop somewhere that just will completely take me out of my comfort zone.

Sukrutha Bhadouria: Yeah. I mean there’s always that great reading resources, too. I always ask people for book recommendations, and I most recently was reading A Hard Thing About Hard Things, again, because I really like the takeaways from that, especially when I’m going through like difficult decision making situations at work. How about you, Angie?

Angie Chang: I’ve learned a lot by reading books that have been referred to me, also reading about other amazing women. For example, last year I read about the Molly Bloom story, which I thought was very interesting, about how she kept trying to stay relevant in her business. I’m always asking people what podcasts they listen to, what newsletters they subscribe to, how do they get their news, how do they get their learning, to kind of make sure I’m doing the best I can to learn, aside from occasionally watching some business economics YouTube videos, which I feel like make up for the zero business and economics classes that I’ve ever taken at a university.

Sukrutha Bhadouria: I’ve been really listening to a lot of podcasts that are tech related, and tech news, and interviewing tech leaders, like Masters of Scale has been a really good learning for me as well. Do you all listen to anything on the go, or audiobooks, anything like that?

Rachel Jones: I listen to so many podcasts just because I do consider myself a lifelong learner, and I love to learn. One thing that I learned about recently is kind of the difference between learning just for learning’s sake versus learning with intention. Because when I think about learning and approach it, it’s not all specifically tied to my career. I think it was interesting you were talking about listening to podcasts that are specific to tech. I listen to so many random things that have nothing to do with my work, but I still think that’s valuable, just like the process of learning. What do you think about that, like having intention behind learning?

Sukrutha Bhadouria: I think that’s great, because when I’m trying to learn a new programming language or anything new in technology, I find that I learn best when I know that I’m trying to build a project, or make something, and I’m learning for that purpose. I definitely pick it up much faster. How about you, Angie?

Angie Chang: I definitely think it’s very smart to think of it as learning with intentionality. On a side note, what I thought of immediately is sometimes we get our inspiration in the oddest places, and I feel like watching something like the West Wing now has actually been one of the more illuminating things I’ve done. Watching the West Wing isn’t something you would tell somebody to go learn, but you learn so much by watching the scenarios you learn about with the American work culture, and as someone who was a first-generation immigrant you’re like okay, I get it now. You understand things more, things people say, why they do what they do. It made Imposter Syndrome seem less scary. I think learning comes from all different unexpected places.

Gretchen DeKnikker: A agree with Sukrutha on kind of if I’m trying to learn something with intentionality then having a way to put that into practice right away is helpful, but then kind of tying back to what Rachel was saying, and I think we might agree on this, is that sometimes I go learn something brand new that’s like for no fricking reason, other than to take me out of … Like I went and took a Taiko–like a Japanese drumming class because it was just so far outside of anything I’ve ever done. Also, I’m a terrible drummer, if anybody is wondering. You will not be coming to one of my shows anytime soon. It’s something so different that you have to put all your attention into learning that one thing, and while I’m putting all that attention into one thing I can’t think of all the other crap, so it freshens me to go back and tackle the other problems that I have.

Angie Chang: We’re not necessarily learning, but we’re optimizing for future learning.

Gretchen DeKnikker: Or just like optimizing for your brain being fresh enough to absorb the information that you’re trying to take in right now.

Angie Chang: We do need breaks. I do find that sometimes when you’re just working on a really hard problem, you need to take those steps outside your usual realm.

Sukrutha Bhadouria: Yeah, you’re teaching your brain how to learn. This topic about learning is so fitting right now, because we’re always competing with ourselves, or with the situation around us. You want to be doing your best, and you’re wanting to put yourself in a situation where you’re constantly either learning or growing.

Angie Chang: This learning topic came up at one of our Elevate panels. We had a learning development expert who used to work at Facebook, Minji Wong, talk about being intentional and learning.

Minji Wong: In my thirteen plus years of experience, having worked at various tech companies, eCommerce companies, retail, and various industries and sectors, I’ve managed several leadership programs and experiences with high-performing individuals. In my conversations with them, what do you want to do, what do you want to be, oftentimes the response I’d get is I just want to develop these specific skills, or I want to be able to explore, kind of learn and develop myself in my career. I rarely actually had a response that would let me know this is who I want to be, and this is where I want to go. It’s super important to realize that and recognize that because if you don’t have that end goal or that end destination, anything and everything you do may not necessarily contribute to that end goal. I realize nothing is ever static, and in fact things are dynamic, things can change tomorrow, or even yesterday. Again, highlighting the importance of having an end in mind, knowing that that can change is very important. When we think about this learning journey, oftentimes, and in my background having spent 13 plus years in leadership development and learning and organizational development, I oftentimes hear people say I need to develop the skill, let me go to this training, and then I’ll be cured and I’ll be healed. The reality is a lot of our learning, 70% of our learning actually occurs on the job. That’s through the stretch assignments, that’s through the cross-functional work, that’s through being thrown a new project that you have very little experience having really managed through and learning literally in the trenches. 20% of learning actually occurs through conferences like this, where we can hear from amazing and incredible women in the field, and where we can learn and develop community and connection from each other. It’s also through coaching and mentoring.

Rachel Jones: It’s interesting that Minji says 70% of learning happens on the job. Has that been your experience?

Sukrutha Bhadouria: I agree with that. I definitely saw myself, I felt like I got better at my job from the skills I picked up at work. You can’t learn everything in a classroom, but you learn practical skills that you will need just by doing some of it, doing some of the work. What do you think, Gretchen?

Gretchen DeKnikker: I think I’m definitely an experiential learner. I’m definitely one of those start in the middle kind of people, and then I go back and read the directions if I haven’t figured it out.

Angie Chang: I absolutely think that a lot of the learning happens on the job, from learning new ways to do things from other people, but also there’s a fair amount of work that goes in after work,trying to just find new things to learn, going to different events to try to figure out what’s coming, and definitely there’s maybe 70% on the job, and then more after work.

Gretchen DeKnikker: I think what’s always attracted me to startups is that there’s the opportunity to learn so many things, and to get your hand in so many things, to get in over your head all the time, because there’s not really anyone on the team who knows how to do something, so anyone–it just has to be done, and so there’s a lot of learning that can happen there. For me, sort of that get thrown in the deep end and figure out if you can swim kind of learning is really the kind that motivates me.

Sukrutha Bhadouria: I feel like when you’re working in tech, your skills become out of date so quickly, and you have to relearn something new. I find that just the stuff that you learn on the job is just learning how to learn, and that to me for sure is more valuable than anything you could pick up anywhere else. That–it’s been similar for me, where I learn more on the job.

Gretchen DeKnikker: I think that’s definitely one way that I do see a value in seeking additional bits of knowledge outside of work, of taking a class or even considering going back to school. I think it’s always a really good mix. You can’t get everything from one source.

Sukrutha Bhadouria: I find that when you’re in a larger company there’s so many organized trainings and organized programs, but there’s also resources now that you could take advantage of outside of work, if you work at a smaller company that doesn’t have these programs. I suppose if you were more intentional about it, like Minji has mentioned, if you knew exactly what you are learning it for, it will make it easier to identify what these resources should be, because I feel like now there’s so many resources, just picking which one is going to work best for you is what’s the first challenge. Being really specific about what your end goal is once you’ve acquired this skill …

Angie Chang: It’s great advice. I’m a terrible learner. I’ve never been good at all.

Gretchen DeKnikker: She’s lying, people. She’s lying in podcast land.

Angie Chang: I’m much more of a learning by doing is I suppose the best thing I could do, is finding opportunities to either say I’m gonna write three times a week, as I did at Women 2.0, or saying I’m gonna write one blog post a week or a month is more realistic. By doing things over time you get better.

Gretchen DeKnikker: I think there’s sort of the different sources. When you’re trying to gain a skill, a class is a really great thing. Way back in the last century, when you had to go learn Excel and Word, and Access, go look it up on Google, it was really cool, now there’s Airtable, there was sort of that skill gaining that you do earlier in your career, and then there’s sort of the management training, which maybe you can get from a classroom, but I really find–Angie talks about reading people’s biographies and stuff, and I feel like I’ve learned more … Like I read Jack Welsh’s book, way way back, and it still influences me. It’s been like twenty years since I read that book, and it still influences how I think about people and managing things, and sort of how things interrelate.

Gretchen DeKnikker: I think it’s different for everybody, sort of the type of thing that you can tap into, that will resonate with you, particularly when you’re trying to learn about being a better manager, which is essentially learning about being–more about yourself.

Sukrutha Bhadouria: For more technical learning, I do find it helpful if there are the online courses. I can go back even if it’s something I learned in college, I can go back and go through those problems again. There are various resources now that sort of make the classroom experience a little bit easier, because you can go back and learn. I still feel like you have to go out of your way to get more information, and learn more, and improve. I suppose if you do have a full-time job, balancing what you’re trying to learn with that can be difficult. In our last Elevate conference, Sophia Perl did talk about how she does the balancing act between learning and life, basically, balancing it with her day to day. She’s a director of product at Oath, and has formerly worked at Yahoo and eBay.

Sophia Perl: I think we all have learning methods that really resonates well with us, meaning when we learn through a certain method the content sticks a lot. If it’s something similar to what I go through, that’s usually like reading a book or taking a class. I would love everyone to open up your minds and think about, look. You could either wait for that perfect moment where you dedicate a lot of time and maybe energy to do your preferred learning method, or you could actually–I would say get your second or third best learning method. Think about finding opportunities where the learning method meshes more well with your day to day life, instead of finding that perfect moment where you have to dedicate a lot of time to learn about something. That’s something to keep in mind. I’ll give you an example. The one that actually sticks out the most is Overdrive, which is like a free version of Audible. Audible is the monthly subscription that you get on Amazon, you pay $15 dollars a month to access a bunch of audio books. Overdrive is actually connected to your local library, so if you don’t have a library card already I encourage all of you to go get a local library card, and then hook it up to Overdrive. What Overdrive allows you to do is to download eBooks or download audiobooks for free. I actually did a sort of a side-by-side comparison between what I could find at my library and what I could find at Audible, and I found about seventy to eighty percent of the books that I was personally interested in, I could find for free on Overdrive. Consider leveraging apps to help make it easier to consume information. In conjunction with leveraging apps, you want to think about what devices you want to be using, and for what–when you would use those devices. In the morning, I have an Echo Dot, I have two waterproof speakers, and I have an iPhone [inaudible 00:17:24]. This is in the shower. I don’t do this all the time, but I have been known to watch YouTube videos of people lecturing or different workshops. I have it pressed up to the glass of my shower door, and then I listen to the talks while I’m in the shower. If you think about it, what times do you have where you could actually listen to content? For me in the shower, I’m spending fifteen, twenty minutes in the shower. Then you could read the rest driving, and in the evenings. In the evenings, it’s great for me because I’m actually not multitasking as much. After I’ve put my kids to bed, and later in the evenings, that’s when I find time to meet with people who are more flexible in terms of meeting late evening. I have my laptop and phone, so I usually do hangouts and so forth.

Rachel Jones: Have any of you ever had trouble balancing learning with your day to day?

Angie Chang: The word balance kind of throws me off because I imagine like a world full of balance, where I get to go to my job, and go to yoga and a spin class. I don’t see a problem balancing things. I see more just jumping in, and if there’s a problem at hand working to find the solution. If there’s a project that needs to be done, or if there’s performance management that needs to be done, just doing those tasks. The issue of balance hasn’t been something on my radar.

Gretchen DeKnikker: I think I’ve definitely struggled, and I think the times that I’m struggling most in my job are when I’m not carving out that time for learning, whether it’s learning a new skill, or just some random thing, or whether it’s sort of reading a book, like a management book, that’ll help me sort of step back from my day to day, and just get out of the weeds and see things from a higher elevation, or just learning more about something that I’m struggling with, that’s very directly relevant to work. Certainly the times when I’m most overwhelmed, a great thing for me to do is to go use a different part of my brain.

Sukrutha Bhadouria: I can relate to that, for sure.

Rachel Jones: Is there anything you heard from Sophia’s suggestions that you think would be helpful in fitting learning into your daily life?

Gretchen DeKnikker: I think for me one thing that came up, I totally get shoving all the things in, and trying to sort of maximize a convenient learning schedule, but when I was hearing Sophia talk about doing it in the shower, I also thought about having–while we do this stuff and we try to fit learning into everything, we don’t leave time to be alone with ourselves and our own thoughts. For me, the shower is sort of that time, and but I think wherever you want to do your learning, but always just keep in mind that it doesn’t always have to be this input from outside, that being alone with your own thoughts is also a super-valuable use of time.

Sukrutha Bhadouria: I love how she has different styles of learning, depending on time of day. To me, I realize now that I have something like that, where it wasn’t intentional, but it’s just like listening to something that’s more audio in the morning, but being able to watch stuff after work, so that sort of thing definitely spoke to me.

Angie Chang: Absolutely the timing thing was really interesting. Actually I drink coffee in the morning, therefore I can do certain things in the morning versus at the end of the day.

Gretchen DeKnikker: But you’re like a night-worker person, Angie.

Angie Chang: I know.

Gretchen DeKnikker: She’s like Slacking me at 10:30pm and I’m like I don’t care, this is not my learning time.

Angie Chang: I think there’s different times for everything. Late night, I like to write good blog posts. During the early day, I get to do more of the things on my list of things to do.

Gretchen DeKnikker: And also not talk to people. Angie does not like people in the morning.

Angie Chang: No.

Sukrutha Bhadouria: Just hearing everyone talk about learning and the various resources we can find, it makes me think this topic is going to be really valuable for our listeners, too, because I’m sure everybody who’s gonna be listening is going to have their own methods of learning, and their own resources that are always great to share.

Rachel Jones: Once you’ve actually set aside that time, or figured out how you’re gonna work learning into your day to day, how do you approach learning things that are kind of outside of your comfort zone?

Sukrutha Bhadouria: I find that I’m more open to learning when I convince myself I’m going to be amazing at it. I’m just like I’m gonna be great, I’m gonna ace this. For example, I redid this algorithm class on Coursera, and I traditionally had struggled with it because it’s a pretty tough class, and the turnaround time for the assignments is really short. I just had to motivate myself and coach myself to feel like this is time I’m gonna set aside regularly, and I convinced myself that I had to look forward to it because it was going to be awesome getting a good grade on it. I found that I’m just not open to learning when I feel like I’m not going to do a good job, so kind of both ways just opening your mind up to being ready for learning is what I try.

Angie Chang: That’s an awesome idea about pumping up yourself to be excited to learn. I don’t know how to do that myself. I don’t learn as much.

Gretchen DeKnikker: I’m going to punch you for saying that. It’s so not true. You spend so much time poking around learning about little, little things. You’re not even allowed to say that anymore.

Angie Chang: Little things, but it’s like I don’t take, I think the problem is I don’t take a class…

Gretchen DeKnikker: No, you spend all day learning a ton of things.

Sukrutha Bhadouria: There’s different kinds of learning.

Angie Chang: I guess, yeah, I just spend a lot of time pecking around the internet, and figuring out what I need to read, so it doesn’t feel like learning, just kind of like constant exploration.

Sukrutha Bhadouria: I guess you’ve turned it into fun, which is why your mind is open to learning.

Gretchen DeKnikker: Which is why you don’t need Sukrutha’s pep talks. You’re just already into it. Although now you need her pep talk to convince yourself you’re awesome. So, yeah. I think I need structure, and so I specifically do set things up in a way where I have to go, or I have to finish something. I just took a few short courses at City College, they have a whole diversity and social justice certification. I purposely took the courses for credit, even though I’m not looking to, and they encourage you not to take them for credit, but I was like I will put so much more into this because of course I have to have an A, of course. Nothing else is an option. I’m gonna spend even more time doing it. Like to Sukrutha’s things some of these classes, I took the racism and sexism one, and those required me to pump myself up in a different way, of like this is gonna be hard and challenging, but you’re gonna come out knowing a lot more than you did going in, but you’re gonna be so fucking uncomfortable the whole time that you’re there, and being open to that, and so a different kind of pep talk to open myself up to the learning.

Rachel Jones: I’ve definitely had experience with how much the way that you’re thinking about what you’re gonna learn affects your ability to actually learn that thing. I believed for my whole life that I am not good at math, so that just really sets me back from approaching any math. I think your brain has so much power, and when you are really thinking about the mindset that you’re bringing to learning it makes such a big difference. I think it’s interesting even, Angie, how you don’t think of things as learning, even though it’s definitely learning. That might actually be better for you, your mindset is just like oh, I’m just poking around the internet …

Gretchen DeKnikker: It doesn’t feel like work, or something.

Rachel Jones: Yeah. It lets you take in that information a lot better than if you had been saying oh, I need to go learn this thing, let me sit down and do it. It’s more of a natural part of your process. I think, yeah, the mindset that you bring into learning makes a huge difference, and that really ties into something that was shared at our event with Postmates.

Angie Chang: When we were at Postmates for a Girl Geek Dinner, we heard from Christine Song, who is a software engineer, and she talked about hacking her brain to realize that she could become an engineer from a philosophy major in college.

Christine Song: When you look up learning how to learn on the internet, you get a lot of really cool techniques to hack your brain, but I think the precursor to all of these learning how to learn techniques is the idea that you have to change your relationship with your brain. I started learning how to code about a year and a half ago, and when I first started learning how to code, I came from a purely non-technical background. I was working in the restaurant industry for about five years before this, and that entire time nothing that I did was had immediately transferrable technical skills over coding. When I decided I want to learn how to code, this is kind of what my brain told me. The moment it thought of engineering, it thought immediately of math.

Christine Song: Historically, my experience with math is not the best, and so the moment I associate anything with math my brain kind of went into a haze, and it started thinking incompetent, because you never in your past have ever been good at math, so why do you think you can do this now, which immediately leads to I can’t do this, and when I realize that I can’t do something I like to default to three different modes to alleviate my stress, which is either one, screw this, I’m gonna move to the woods and live off the land. It’s a very real fear, I’m not kidding right now. Or I’m going to meet up with friends, or I’m going to go on a Netflix binge. Up until this point, I have always felt like what my brain told me, it had the culmination of all my experiences I’ve ever experienced in life, and so if my brain is going to tell me I can’t do something it’s probably right. Right? Wrong. Your brain is a tool. It’s not something that can tell you what it is you can and cannot do. What you do with your brain is you learn how to learn, which is why there are so many cool techniques about like hacking your brain, thinking about the ways that you can hack your long term and short term memory, using mnemonics to remember things. So I tried it again. I was like all right, look, what I’m doing right now isn’t working, so I’m gonna try and equate engineering with something that I’m very familiar with. Up until this point in my life in college, I majored in philosophy and my emphasis was in logic. Logic looks just like math. You do proofs with Greek symbols and variables, and you do proofs much in the way that mathematicians do proof. Once I realized that my fear of math was completely irrational, I ended up learning more about computer programming, and now I’m a back end engineer here in Postmates. The things that you think you are capable of doing, if you keep thinking those things and you give power to that thought, and you let it dictate your actions, it’ll become true. If you are able to take a step back and realize that isn’t the definition of who you are, and you can do whatever you want because you do with your brain what you wish to do, then you can like me go from a completely non-technical career into being an engineer in the field.

Sukrutha Bhadouria: I definitely think when I shut my mind to opportunities I’m obviously not going to be as receptive to learning or improving. This is really fascinating to me how she went through this whole mind game basically to convince herself of why the emphasis being on logic would then help her be better an engineering. I find that this is probably something that a lot of young girls must go through, because it starts so young in middle school and high school, where they feel like they’re not the right fit. This is really an interesting perspective. What did you think, Gretchen?

Gretchen DeKnikker: I think there’s sort of the two parts, sort of how she hacked her brain to develop the capacity for this learning, but the other part is sort of the stories we tell ourselves, and so even Angie is saying earlier I’m not much of a learner, and I threatened her with violence, and Sukrutha, we’re just like no, that’s so not true, but I think that’s maybe the deeper part of this, is how do we get in our own way, and keep ourselves from learning things just based on even Rachel saying I believed I wasn’t good at math, so I wasn’t good at math, and questioning even just those baseline assumptions that we have about who we are and what we’re good at, and have we challenged that, any of it, recently. I love math. Just tell yourself that every day. Math is so great.

Angie Chang: You don’t have to be great at math to do things that you thought needed a good math background. I had an English and Social Welfare degree, and my first jobs were in engineering. I never thought that would hold me back, but that’s also because I had experience as a web designer and a webmaster, and people tied the dots for me, they’re like oh, yeah, you could totally be an engineer. I was like, really? I thought I designed websites. They’re like no, you can do engineering. I’m pretty grateful to people for making that connection for me, so I could get those jobs.

Sukrutha Bhadouria: I think that there’s also a variety of things, you might think you’re not good at something just because it was not taught to you the right way, or the resources just didn’t work for you. I know a few people who I work with now who didn’t actually do that great in their first computer classes. I know it took me awhile, but I definitely gave myself a lot of chances. Be patient with yourself, I guess, is what I would say. For sure, when you hear the story about math being really hard for Christine, and she says everything, all of the Greek symbols made it complicated for her, I remember feeling that way too. But I think just staying positive helped me.

Angie Chang: I think going with the expectation that it’s going to be hard is probably a good one, but no one ever did anything that was easy, and a lot of things we learn are very hard.

Gretchen DeKnikker: Also not starting anything without first questioning why am I learning this? Because I have to? Because someone else said I should? Because I have this idea that something requires it? If you really are like–no one enjoys doing something that they really suck at, and then also do I really need to know how to do this? Like there was a really short time while I was a founder where it was like I’m technical enough of understanding how everything goes together, what’s a coding language versus whatever else, but I thought for awhile maybe I should try this Python class online, and then it’s like as a founder is this where I’m really going to add value in the company, or is it all the things that I’m already good at, and I’ll maybe just leave this to the engineers, but it sort of subscribed to this idea in Silicon Valley like everyone needs to learn how to code. Actually no, you don’t, not everybody needs to.

Angie Chang: That’s a good point.

Sukrutha Bhadouria: Yeah. I struggle with this. Do you try to improve your weaknesses, or should you be focusing on strengthening your strengths? It’s a fine line.

Gretchen DeKnikker: I think so. I think early in your career you should be trying to sharpen your weaknesses, because you don’t know if there are weaknesses or just a knowledge gap. As you get older, it’s like you know what, I’ve always sucked at that, I’m never really gonna be good at it, and I’m in a position where I can hire people on my team who are awesome at that, and then they can excel at it, and I don’t have to touch it, and everybody is happier. Right?

Sukrutha Bhadouria: Totally.

Gretchen DeKnikker: Angie, what are you gonna take away from this little time we spent talking about learning?

Angie Chang: I’m taking away that learning happens all the time, and is not just taking a class. It’s being aware and taking in inputs throughout the day, and to surround yourself with people that are able to help me see that.

Sukrutha Bhadouria: I feel like for me I learned that everything is difficult for someone. There’s always gonna be someone better at something than you, and you’re always gonna be better than someone at that same thing. You know, keep your mind open, and that’s when most learning will happen, I think.

Gretchen DeKnikker: I think I’m going to be thinking about, Christine’s story really struck me, and it’s like what are the stories, like is there another story I’m telling myself about something I’m not good at, that’s keeping me from or something else about it, or that’s not an open path for me, and really be like okay, what foundation is that assumption based on?

Gretchen DeKnikker: Rachel, what do you think?

Rachel Jones: I think my takeaway is I should go take a math class. It’s not too late for me.

Sukrutha Bhadouria: Yes. Maybe that can be our next conversation.

Gretchen DeKnikker: Next podcast, Rachel’s learning on math.

Rachel Jones: Check in on how that’s going.

Angie Chang: Thanks for listening. Tune in next time.

Rachel Jones: This podcast is produced by me, Rachel Jones. To learn more about Girl Geek X, or buy tickets to our next dinner, visit GirlGeek.io. You can also find full videos and transcripts from the events we discussed today. If you’re interested in hosting a Girl Geek Dinner, email sponsors@girlgeek.io.

Angie Chang: This Girl Geek X Podcast was brought to you by Postmates. Postmates helps people unlock the best of their cities and their lives with an insanely reliable on demand anything network. Launched in 2011, Postmates pioneered the on-demand delivery of movement in the US by offering delivery from restaurants and stores previously only available offline. The company now operates in 550 US cities, as well as Mexico, and provides access to over 200,000 merchants.


Girl Geek X Podcast Hosts:

Angie Chang

Sukrutha Bhadouria

Gretchen DeKnikker

Rachel Jones


Girl Geek X Podcast Guests:

Minji Wong, At Her Best Founder

Sophia Perl, Oath Director Product Management

Christine Song, Postmates Software Engineer


Girl Geek X Podcast Sponsor:


Episode 2: Career Transitions

Angie Chang: Welcome to another episode of Girl Geek X podcast, connecting you to the best insight from women in tech. I’m Angie, founder of Girl Geek X, and this podcast brings you the best of Girl Geek Dinners, where we’ve been elevating women in tech for over 10 years.

Sukrutha Bhadouria: Hi, I’m Sukrutha. CTO of Girl Geek X.

Gretchen DeKnikker: And I’m Gretchen DeKnikker, COO at Girl Geek X.

Rachel Jones: I’m Rachel, the producer of this podcast.

Angie Chang: And today we’ll be sharing advice on navigating career transitions.

Sukrutha Bhadouria: This is a really interesting topic for me, because I have always struggled with having this five year plan or ten year plan that actually I could relate to. Sure, I would create one, but I never really stuck to it. What did you all feel like, after listening to topics about career transitions?

Gretchen DeKnikker: My career is just … I’m 46 years old. I’ve never had a five-year plan, and since I’m in the middle of like my midlife crisis of like I don’t know what I want to do with like the third wave of my career, I sort of wonder if maybe I should have. Maybe you can help me, Sukrutha, write my five-year, like, here’s what you should do with the last few years of your career. I think I’ve always just followed my heart and I’ve always sort of followed the next thing that felt like the right thing. And that’s advice that I give and sometimes, lately, now that I’m in this cloud of, I don’t know what I want to do next. I wonder if it’s good advice, but I’ve always given the advice of, don’t be afraid to take a left turn. Have a plan, have a good understanding of where you’re headed, but don’t be afraid if something comes up and it doesn’t fit the plan that it feels like the right thing to go explore that. Especially when you’re younger where you really can’t screw up. You really can’t, any career thing you do, particularly in your twenties, you really can’t screw up any path, you could just find new paths and new passions by leaving yourself open. Because you really don’t even know yourself as well as you’re going to as you get older, so you don’t have to have it all figured out when you’re 27, or even 32.

Angie Chang: It was at a Girl Geek Dinner that I had met some very inspiring women in tech who were doing things like having a kid and writing iOS apps on the side, or women who were product managers at really admirable companies, and they would tell me how they were still interviewing for new jobs and opportunities and always keeping a door open and looking for the next best thing. That always surprised me but also made me realize how we have to be on top of our own careers, even when everyone else thinks that we have a great career already, there are those women who are already thinking about what’s next as well. So, we’re always having to be open to going to networking events, talking to more people, and looking around the corner at what’s coming because we are in the silicon valley, of defining the next role, the next field, the next industry, is our responsibility we have to take upon ourselves.

Sukrutha Bhadouria: I wonder if you’re more likely to make a career transition when you have no options, or when you have a backup option that’s not scary.

Gretchen DeKnikker: That’s a good point. Yeah.

Sukrutha Bhadouria: Because I remember reading about this. It’s not a ladder to the top. It’s like a jungle gym, right? There’s so many different parts to go to the top, and every experience you’re gaining is gonna help you in the long term. But with career transitions, they don’t necessarily have to be a lateral move. It could be that you’re taking two steps back to take one giant leap forward, and it’s just thinking about that in a way that it’s not detrimental to your career. It’s what will make it easier for you, I think.

Gretchen DeKnikker: Do you have an example of what you mean when you take the …?

Sukrutha Bhadouria: Yeah. For me, after 5 years in my first job, I wanted to change jobs because I felt I wasn’t learning. I could’ve stayed as the big fish in the small pond, but I recognized that if I stayed I would just not grow.

Angie Chang: And just personal context, I remember when I met you, you were a software engineer in test end dev quality engineering and I was always asking you about that, and then you made the transition to become an engineering manager.

Sukrutha Bhadouria: That’s right, so what happens when you make a move like that is that you’re putting yourself into a situation where you’re a beginner again. So you’re having to prove yourself again and you would think, oh my gosh, that’s gonna take longer, that’s gonna cause a delay in my growth, but growth means so many different things. You have to decide what growth you’re after.

Angie Chang: Absolutely. I think people should always be looking to apply to new opportunities and roles you never thought about, just to have those interesting exploratory conversations of how they might have value to other industries and companies and who knows, you might get a really interesting offer, you might make some good connections. Maybe increase your salary.

Rachel Jones: During our panel on engineering leadership, a few women actually shared thought exercises that they’ve used to help chart out their careers. Sukrutha, could you tell us more about that panel?

Sukrutha Bhadouria: Yeah, so Angie and I met Arquay Harris, and she is a Director of Engineering at Slack. And the really, really fun tidbit we learned about her that night was that she got her job at Slack through a Girl Geek dinner that she attended a few years ago. We hear great things about her. She’s a terrific manager, her past experience includes Google and CNET, and at the dinner we asked her about what she thinks about her career at engineering leadership and how she thinks of it at that Girl Geek Dinner. That evening, we also met Kimber Lockhart, who is now the CTO of One Medical. She’s spoken at a past Girl Geek Dinner when Box sponsored it while she was a VP of engineering there. Consistently she’s given great advice about framing your career and thinking more about the challenges that you might face, and working around it, and building your career path. Here’s what she had to say.

Arquay Harris: I try to think about it in terms of what is the highest aspiration that I have for myself? And a lot of people think about five year plans and if I look back at my life five years ago I probably would not think that I would be in the position that I’m in. But what I mean by highest aspiration is, is it to be CEO of a company? Is it to be CTO of a company? Is it to just continue to be director of engineering? And knowing that helps me figure out how to chart my career. It’s like the north star. So for example, if I said, I wanna one day be CEO of a Fortune 500 company, I would probably make different career decisions. I might try to get bigger and bigger teams, I might move jobs more often, I might have different goals. Up until very recently, my aspiration for myself, I like the director of engineering level. I like the ability to mentor people on a one-to-one level. I like that human interaction, and I feel that in some roles, like if I’m CTO of a company that has 10,000 engineers, it’s probably difficult to do that in the way that I would like to do that. Not that it’s good or bad, that’s what I see as the highest aspiration for myself. But I think, though, I would say if you had asked me that today, maybe that answer is different, right? And so understanding that and knowing that as my experiences change, that that aspiration maybe changes, and then maybe I’ll have to think, maybe I should do things differently, I should network, maybe I should do things like Girl Geek Dinners, right? So you get more exposure, whatever that happens to be, I think understanding what that north star is pretty important.

Kimber Lockhart: I occasionally give a workshop on career paths and thinking about career paths. And one of my very favorite exercises from that workshop is that we draw three different pictures of things that could happen that might be dream career moments. And so I draw, for example, well maybe I’m gonna quit my job and join a venture capital firm, and go interview a bunch of heads of engineering, and write a book about everything I just learned. Wouldn’t that be fun? My other one’s, I’m gonna be the CTO of the US and won’t that be very exciting except maybe not right now. The point of the exercise isn’t so much the crazy visions, but the part where you look at of those visions and say, what about this can enhance my career right now? So I did that crazy vision exercise around writing that book, and I said, you know what I wanna do? I wanna get my ideas out there. I want to start writing. And so about a year ago I said, I’m going to make time to start writing essays, and started posting on Medium, something anybody can do, and found that it was a wonderful way to grow my career in a direction that it hadn’t been before. It wasn’t just about aiming for what is the next level up in the management chain, but rather, what is another dimension that I can add to my career today?

Rachel Jones: So have exercises like what these women suggest been helpful for any of you? Sukrutha, I know you mentioned creating a five-year plan.

Sukrutha Bhadouria: That evening, when I heard Arquay talk about her highest goal and her highest aspiration, that made me go home and think about, what is my highest goal or highest aspiration that I want? And do I want to continue where I am or what my north star is, like she said. I try to chart it out that way but it’s not always that I will follow it exactly to the tee. But it makes it easy if I have multiple options like Kimber called out, right? Think about three different options for yourself and design according to that. I’ve found that it’s been a bit easier for me to take risks because the one thing that I try to avoid is to just stay where I’m comfortable, because then I’m not really growing. What do you think, Angie?

Angie Chang: I think having those three different scenarios is a really great exercise. I’ve heard people who invested in having some professional coaching have mentioned having this framework or exercise of thinking through at night, what are these three diverse things that could happen in your life? So that gives you not just one point. If you don’t succeed in becoming a CTO, you might wind up being a really great security leader at a different type of company. There’s different ways to think outside of that very rigid box of what we see as success.

Gretchen DeKnikker: For some reason this is also making me think about when people talk about going back to school. People are always seeking advice. Particularly, going to business school and getting their MBA. And I think the advice I always give is, well what are you going to do afterwards? And if you don’t have a clear goal of what the outcome is, what the thing is that you’re gonna get, then there’s no reason to give up two years of income and two years of your life, and then business school is hard anyway. It’s great, it’s fun, but if you don’t have a specific outcome that you’re looking for, and this would apply to school in general about not doing it. And I think that Kimber’s way that she looks at it is one of those lenses of oh, well what if I went back to school? It’s something I think about all the time. Mostly because I just think oh, I don’t wanna work anymore, and then I think, okay, so you’re gonna give up how many years of income and run up a whole bunch of debt probably? And then what, exactly, is the job that you’re gonna have afterwards? Are you just kind of looking for an academic vacation?

Sukrutha Bhadouria: Yeah, so I had to actually go through an exercise similar to this when I was thinking about what I wanted to do next when I was still an engineer. And so I worked with a career coach that was assigned to me through a work program and she asked me to think about my three options, so I said, all right, so I want to stay in tech, I know that. I could be an engineering manager, I could move in to product management, or I could remain an individual contributor and engineering leader. And so she asked me questions like, what is it about that role that you think you’re going to like, and what do you think you’re not gonna like? What do you think you’re going to be really, really good at, and what about those roles do you think you want to be good at? So just working through an exercise like that really helped me.

Gretchen DeKnikker: Angie, you decided to kind of go from your pioneering Women 2.0 days, and then you made the transition to work at Hackbright. What was your process there?

Angie Chang: You have talked about going to business school, and many people I know that go to business school wind up becoming product managers. As someone who’s been a product manager twice, I found that it’s not necessarily about the title, but it’s about the work that you do. And I was very attracted to the idea of Hackbright, which was outside of anything I’d done before. Joining a very tiny crew of people who are trying to do an experiment called teaching adult women to code and get jobs in tech sounded very exciting. So I jumped for that, wound up being a good decision and a good pivot in my career, because I was able to also change what I had been doing. Because previously I was in product and engineering, I also was writing, and then through joining a place like Hackbright I was able to join the business department and work under the CEO of my first official business role. And from there, after four years, I continue to bring that business lens to Girl Geek X and to my next career, and so it’s been a great pivot that I didn’t plan, but just followed the opportunities as they came. And in fact, I remember that the founder of Hackbright came to a Girl Geek Dinner, and said, hey, this is my idea, and I was like, interesting. And the fact that he dared to come to the Girl Geek Dinner and be an ally and pitch what he was working on, and I followed through and visited the campus, I was like, okay, this is legit. This is a really good initiative. There’s good people here. So I think you have to really just open yourself up to these opportunities and follow through with them if they turn out to be right opportunities.

Sukrutha Bhadouria: That’s great.

Rachel Jones: It’s really helpful having these tips for ways to think through what you wanna do in your career, but how do you know when it’s time to actually start taking those next steps?

Gretchen DeKnikker: I think for me, because I’ve always done really early stage companies, there’s usually the coming to terms with my current role and how I feel about it, and then what do I want to do next. The first part of it, for me anyway, is when you start finding yourself unhappy and you start thinking about, okay, what are the ways that I could change this, right? Do I need to change the role, do I need to learn some new skills, do I need to try to have a different manager? What are the ways out of it? And for me, particularly in small companies, there aren’t a lot of those opportunities and options. So then it becomes okay, am I happy more days than I’m not, and then when you get to the point where you wake up and you’re like that was three days this week that I woke up and went, ugh instead of thinking, oh my God, I have twenty things to do and hopping out of bed because you want to get them done. And so then coming to the all right, so what do I like about this job that I would like to do at my next job, what do I not like about this job that I don’t want to do at my next job, and starting to look at it that way.

Angie Chang: And oftentimes I think the scariest thing is just starting and being able to say to your friends when you’d see them for brunch and saying, I’m gonna be open to new opportunities. Please let me know if there’s anything interesting that comes along.

Gretchen DeKnikker: Oh, come on. Last time you posted that on Facebook! She was like, not happy. I was like, wow, that is bold. She was just like, hey, I’m opening some new stuff.

Sukrutha Bhadouria: Contact me. I think that was really, really, really gutsy and awesome.

Gretchen DeKnikker: It was amazing!

Sukrutha Bhadouria: I would do that, too. Tell everybody you meet what you want. Someone will make it happen. Because that’s basically you making it happen.

Gretchen DeKnikker: I made a list one time one time of 25 people I was gonna have coffee with, and by the time I was done with the coffees I thought I would have a plan. I was doing customer development for my life, right? And by talking to all these people, a pattern was going to emerge and by the end of it I was going to know what job I wanted. It didn’t totally work out that way, but I had a very good sense of what kind of company I wanted, what kind of leadership team I wanted, what kind of space I wanted to work in, and now I’m still kind of trying to apply that plan, but the process was very worth it. And you get to talk to people.

Rachel Jones: It can be scary thinking through giving up a job that you have to take the next step, even if you are unhappy or you feel like you’re not getting the kind of growth that you need. So how do you navigate that and know when it’s time to move on?

Sukrutha Bhadouria: I think I’m a little bit more risk averse than I should be and so my whole thing is, what’s the worst case scenario? Is staying at my current situation the worst case scenario? Then that’s fine, you know? And so if that’s being without a job, or with a job that I hate, is it okay to just put up with it for two more months? Or is it better to be without a job? That sort of thing is what I try to think about, but it’s not always easy, I’m gonna say that. So, I don’t know how you do it, Gretchen.

Gretchen DeKnikker: So I let myself get to a point where I’m really, really unhappy and then, because I’m in such a state of unhappiness I have a very hard time thinking about what I want to do next because I lack that optimism or the mental space to be able to dream and imagine. So more than once I’ve left a job without another job and not in a good financial situation, but just knowing that that was sort of the forcing function and that that was the only thing that was actually going to make me move forward was to close that door. Because then you’re like, there’s no net! There’s no net! I better get some wings and start figuring out how to fly. I don’t know that I would give that advice to other people. I just know it’s really the only thing that I’ve–

Angie Chang: I think some of the women that I have admired for their careers, they’ve always took time out every year at least once or twice to take a day off and really explore new opportunities even though they had a perfectly great company and job title at the time. So I think when I look at people that I admire but I haven’t done that level of self-investment but I really aspire to do that.

Rachel Jones: I think this conversation about risk relates a lot to a story we heard at our dinner with Quantcast. Angie, can you tell us some more about that?

Angie Chang: A senior software engineer at Quantcast, Malvika Mathur, spoke about moving from her cushy job at Microsoft to a relatively unknown tech startup called Quantcast. And she talks about her thinking on the matter here, this quote.

Malvika Mathur: I joined Quantcast January of 2017, but before that I was working in Microsoft for five years in the India headquarters at Hyderabad. And I joined as a 21-year-old, right out of college, and I was like, damn it, that’s it, I’m done, I’ve accomplished everything that I need to, right? So happy with myself. But the 21-year-old me was really naïve as well. So the first three years were really great, but then, early 2016, my husband and I decided to relocate to San Francisco. I was like, well, okay, Microsoft has offices here, there are teams here, I’m just gonna stick and move to one of those teams. So I was in talks with recruiters and figuring out what I need to do next, and then decided to talk with one of my mentors. And he asked me something really important, something I never thought I’d ask myself. He asked me, why do you want to stay? I was like, why is that even a question? It’s my dream company, the pay is great, all my friends are here, I like the work. Why would I want to move? But then he asked me again, why do you want to stay here? And I thought about it. Turns out the answers for both these questions are not the same. Thought about what I’d done so far in Microsoft, I thought about, if I move to a team here, what would it mean for me? And I realized it’s gonna slow down my growth trajectory. And that’s something that’s really important to me. It’s great to be learning new technologies, but I realized that as a developer, that’s not all I wanted to do. I didn’t wanna just go in and write code. I wanna do something more. Contribute more in the work that I do. And suddenly, life out of Microsoft became like an option. Since I was moving to the Bay Area, working at a startup was suddenly on my shortlist. So I started looking for jobs. And looking for jobs is hard. It is exhausting. And I realized that, subconsciously, that was one of the reasons I didn’t want to move out. I was in a stable job, I was comfortable, I had my friends around. I didn’t want to move. But in the whole process of not looking for a new job, I ended up ignoring the whole process of what’s right for me and my career at that point. So I started to evaluate that, and I started to give that a lot of focus. When I was interviewing at all these companies, they’re asking me questions, but I also made sure I was asking these guys the right questions as well. Because I wasn’t that girl anymore who joined a big company and was excited with any project. I wanted to do more things and I wanted to make sure that wherever I went, I got those things.

Gretchen DeKnikker: I think the really interesting part of Malvika’s story is her manager asking her why does she want to stay and really making sure that she understood it’s almost that thing of, if you were re-interviewing for this job today, would you still want it, right? It’s sort of like that. And having someone who will force you to go through that process of really evaluating, you know, if you were gonna buy a house would you buy the same house that you’re in, or whatever the decision is, to make sure that just because it’s fine, is it great? Is it the thing that’s gonna get you where you want to go. I spent the past few weeks with one of the girls that I’ve been mentoring over the years and she was approached. She’s fairly happy in her current role, but she was approached by another company and they came to her with three undefined roles that she might be good at, and she was really struggling. She didn’t know which one she wanted to pick, and I was like, that’s because you don’t know what you want to do next. So she’s like, and it feels like one is too small, and another one is like one-and-a-half roles. And I was like, okay, well then you need to deconstruct all of these things that they want done and then maybe rebuild the job listing for yourself. But in the process, what I was really hoping she would do was take that and figure out what she wanted to do. Which is, over time, eventually what she did, which was cool, I Jedi mind tricked her into figuring out what she wanted to do next. And then it turned out that she decided she wanted to stay. She saw more positive things in her current role than she saw in the beginning just by contrasting it with the roles that she had going.

Sukrutha Bhadouria: That is such an interesting way of looking at it. Would you chose the situation you’re in now if you had more options? Would you seek out those more options? I think we don’t put ourselves in those situations mentally to think about it until it’s an extreme situation where someone’s asking you, are you having a life event that’s making you think about other options. But it’s really good to evaluate that.

Angie Chang: Now, ten years later in my career, I’m like, maybe people should actively bookmark a day or two in their lives to go and seek new opportunities, despite their happiness level at their company, just to make sure they know where they’re gonna be going in the future.

Sukrutha Bhadouria: Yeah, I think that’s great, to do that regularly. My thing is that, just thinking about this, I  feel like I should make a plan to continuously mentally put myself in that situation of looking for other opportunities, even if I don’t need it, because I might discover something.

Angie Chang: Maybe it’s not even a new opportunity as in a new full-time job, maybe it’s also joining an organization, starting another–There’s so many women’s professional networks that are growing these days, I’ve noticed there’s a lot of women in product, women in data science, women X. There’s so many women that are starting to speak more, there’s so many things you can do.

Sukrutha Bhadouria: That reminds me of what we go through with Girl Geek. We thought about this. Things were going great with the dinners, we were getting great feedback, and we wanted to more, so then we thought of the virtual conference, and then we thought about a podcast. Maybe applying that to ourselves as a self-growth mechanism would also be a good way to do it.

Rachel Jones: Yeah, thinking of it as you don’t have to be in a dire situation or have no other options before you start thinking about ways to move forward is really important.

Gretchen DeKnikker: Yeah, we always tell everyone at the events, build your network before you need it, and this is build your path before you actually want to walk on it. Those two things can definitely go hand-in-hand.

Sukrutha Bhadouria: Or even before you think you need to walk on it, right?

Gretchen DeKnikker: Before you’ve even got shoes.

Angie Chang: Yes.

Sukrutha Bhadouria: How well in advance can you be a planner? But you have to be willing to adapt well, too, because every plan you make may not be a plan that you can follow to the tee.

Gretchen DeKnikker: I’m a terrible plan follower.

Sukrutha Bhadouria: Oh yeah, I’m pretty bad too. I think it’s that thing, the January 1st is when all gyms are so full.

Gretchen DeKnikker: Hit January 15th, it looks the same.

Sukrutha Bhadouria: No one.

Angie Chang: Yeah.

Gretchen DeKnikker: When you’re thinking about when is the right time and what’s gonna be that forcing function, I think it changes in your career, what that thing is gonna be. Malvika’s story was fairly early in her career, right? She was still in her early 20s when she was talking about doing this, and so she made the decision from a place of the role, and then obviously she had this desire to work at a startup, so she was willing to leave this company that she’d always wanted to work for and she felt really proud of working there into something else. For me, my 20s was about gaining skills, my 30s was about becoming a manager and getting to know myself better, but 40s is my way of learning how to be strategic and how to get all of these things to work together where you’re a manager of managers and you can only give so much instruction, but you have to do it in this strategic way that people are going to figure it out and be able to follow. And that’s required me, every single step of the way, learning more and more about myself, and then more and more about what motivates different people. But particularly understanding what you bring to the table, your biases, your weaknesses, and how to hire around that, also, and hire people that balance your weaknesses. And that you’re finding the right people for your team that aren’t necessarily always the people you wanna go have a drink with, but they’re the people who bring something to the table that isn’t already there. So this segues really great into our next section featuring two speakers from Care.com. Dominique is the Senior Director of Growth and Product, and then Sheila Marcelo is the CEO and Chairwoman at Care.com and just an all-around general badass that we were so excited to have speak.

Dominique Baillet: So I’ve actually made a lot of career moves in my life. I’ve had a number of different professional jobs and when I was earlier in my career and where I am now, I’ve always made choices based on where do I think I’m gonna learn the most, and where am I gonna grow the most? And what’s interesting is that, what I need to learn and grow has changed as I’ve gotten older. And so when I was earlier in my career, it was all about skill development. Where can I learn transferable skills, where can I learn the most from mentors about how to actually do something. At a certain point in your career you actually check the competency box, and then you migrate over into a territory of now you just need to be really confident and you need to be able to walk into a room, command that room, and there’s a different level of skill there. And so actually, like many people up here have said, one of the reasons that I joined Care is, I’d gotten to a point in my career where I could check the competency boxes, have the degrees and all of that. But I was in environments where when I looked above, I didn’t really see examples of leaders that felt like, that’s the type of leader I could be. And so I found myself feeling like, wow, in order to continue to rise, I really need to change my style, I really need to do something different, and it felt uncomfortable. It felt like, that was gonna be hard for me to do in an authentic way. And so coming to Care, actually, and being able to learn from Sheila and seeing not only Sheila, but other executives in more senior positions than me and being like, yeah, I get them. And I can get there with the style I have or with the skill I have and there’s other things I need to learn but still feeling like it was possible. And for me that was really important to continue to get that next level of confidence, to truly believe that with what I have, I can get there. And that, frankly, was just a lot harder if I was in environments where I couldn’t look above and see examples of leaders like me.

Sheila Marcelo: I’ll just add to this. It’s so competitive in the Bay Area. Lots of different areas, but even more so here. You get recruiters are pinging you all the time, there’s just so many opportunities. They’re pitching you the next startup or company. There’s great companies. And I think the thing that I’ve been focused on in my career is long-term relationships. I probably interviewed once and updated my resume from one of my first jobs and I haven’t since because I just kept moving from company to company following leaders that I believed in that actually gave me opportunities and continued to help grow me and believe in me. Because that’s difficult to replicate. There will be plenty of startups, there will be plenty of sexy new technology, there will be plenty of great, great opportunities recruiters will always pitch you. And if you follow the opportunity and the pitch, sometimes you luck out, it’s gonna be great, and then you can retire young. There’s a lot of potential of that in the Bay Area. But then there’s also the journey in life, which is who you wanna be around, so there’s definitely purpose. But I think there’s also just the richness of where we spend most of our time, majority of our time in our lives. And so if in fact you enjoy the people that you work with, and you’ve found that tribe, I’m always encouraging people to say, try and stick with that tribe. Move from company to company. I’m completely fine when somebody says, look, we’ve worked together, I’m gonna leave for a little bit, and we’ve had people boomerang back, or we work two, three companies later together. Might not be the next one. So it’s just something to think about as you look at opportunities, is to actually look at the people in your life who’s helping continue to sponsor and help you grow and catapult you to opportunities because they know you well. That’s really what you want to do in your career would be my just small piece of advice.

Gretchen DeKnikker: I think what was interesting about what Dominique and Sheila had to add was in contrast to Malvika, who was earlier in her career, Dominique is really talking about the challenges in your mid-career where you stop looking for skills and really start looking for other growth opportunities. And her advice I found myself just nodding all the way through when she was speaking. It really resonated with me. And then Sheila really just talks about finding the right people and sticking with them. And prioritizing the people that you work with over other things because there’s always that great thing that comes out of it when you have solid team that can really, really deliver things.

Sukrutha Bhadouria: Yeah, so, listening to Sheila’s talk, I wonder if it’s more likely to be women who choose the people they work with over the actual technology or their role or the responsibilities they have been given. I wonder if that would make you less risk averse as a result, because you’re choosing a happy community over uncomfortable situations, maybe.

Gretchen DeKnikker: I totally see why she gives that advice, and on so many levels, I agree with it. I think the only part I feel may be similar to you that how much are you growing if you’re always with these same teams and you’re essentially somewhat in the same role. I’m sure that you’re getting, as your director leaves and they become a V.P. somewhere else, then you come in as a director, things like that. I think there is something about it. I think the other part that I thought about when she was talking about it was, if you stick with these teams, this is sort of how we end up with a lack of diversity. We end up with a lack of cognitive diversity. Having the same people that obviously think similarly enough that you can function very effectively as a team, how much are you growing even just as a human when you always have the same set of people at the table? You see this a lot in Silicon Valley. Teams move around together. But I also think that’s a little bit part of the problem. Or maybe a big part of the problem, I don’t know. But it’s hard to prioritize that versus as an individual I do want to be happy every day and I don’t know that I can change the world by having this job, and should I go take a job where I’m super uncomfortable in this hopes of changing the world, right? And I don’t have an answer for that, but it’s definitely something to think about.

Angie Chang: I’ve always gone for work that was interesting. I never particularly thought about people. I love you all. It’s not a first, right? You do good work and there happens to be good people there, but I’ve never looked at it as people first. I don’t know if that’s a masculine or a feminine trait or anything.

Gretchen DeKnikker: I think it’s whatever it is that makes you happy, right? If I’m around a bunch of people I can’t stand, I’m miserable 24/7, even if I’m solving a really interesting problem, but that’s just something I know about myself. I mean there was definitely one company that I stayed a little bit longer than I really wanted to because I felt like I loved the people there so much and there was still the opportunity to change the role and have it evolve so that it became challenging again, versus trying to go find someplace where I loved the culture and the people that I worked with so much, and that there was that opportunity to change that one piece that would be less difficult than going and trying to find that magical formula that I wouldn’t even have known how to replicate at another company.

Sukrutha Bhadouria: Right.

Rachel Jones: Yeah, how important to you in thinking about new roles you might take on is the culture of the place where you’d be working? Versus what you would be doing there?

Sukrutha Bhadouria: I feel like, for me, it depends. It depends if it’s a culture that I think I can improve or I can learn from. And of course if the work is interesting. Then I will pay attention to the culture. But if it’s 100% toxic and I just don’t enjoy the work challenge, either, then I’m not even gonna try.

Gretchen DeKnikker: I think at this point in my career, in my thirties it definitely had to be a super interesting problem and the people really mattered, too. But I think at this point in my career, it’s so important, particularly because the roles I do, I end up working directly with the CEO, and having that relationship be really solid. And at small companies, the CEO really dictates the culture. And so I think those two things go so hand-in-hand. And those two things have to mesh really, really well or I’m miserable and I can’t even be effective at my job because of that mismatch in styles or whatever it is. That’s honestly maybe the most important thing at this point.

Sukrutha Bhadouria: Is it fair to say then that the best metric to choose to measure an opportunity by is how effective do you think you’re gonna be? Never mind everything else. Do you think that’s a good single metric that we can pick?

Angie Chang: I feel that’s very idealistic. I always want to be effective and I always want to do things that are impactful, but that’s really hard to measure.

Sukrutha Bhadouria: Yeah, I wonder how much you can measure of that before you take the job.

Angie Chang: They’re always trying to sell you, right? You’re only getting the best parts.

Sukrutha Bhadouria: So how I can see how if you already knew someone who was in that company or in that team you could get more insight, so if you already have that connection. Like Sheila talked about.

Gretchen DeKnikker: And I think that there’s, particularly with your manager, because your manager’s really gonna make or break your role. People don’t leave companies, they leave managers. It exists. It’s a saying for a reason, right? And I think if there’s anything that comes up in the interview process where you’re like, that’s probably gonna be an actual thing later. It’s usually just a little sign of what’s coming. It’s kind of that first date, where you’re like, is he a jerk? Should we even go on a second date? Where you’re just really evaluating the basics of making a mental note of that. If we come back to that later and he still seems like a jerk, he’s out.

Angie Chang: So career transitions has been an awkward topic for me, personally. I always found myself, when I start to peter at a job, I found myself not actively self-sabotaging, but not working extra hard to pick up the pieces. And instead focusing my time on my side projects, like Girl Geek Dinners, or Women 2.0. And then almost pushing myself to the point that I would get, laid off with severance, and like, yes, I can pursue my new opportunities now! And I think hindsight’s 20/20, and we always come up with this great advice that we end up giving other people, such as actively seek out coffee conversations, or actively seek out x, y, and z. And we do that, and that’s great, but we should probably also follow that advice that we give other people.

Sukrutha Bhadouria: Just talking through it with all of you has made it so much easier for me to think about what I want to do on a regular basis. Just like everything else, this is a muscle. You need to keep reevaluating what it is that you want out of your career, you want out of life, to be prepared for the sudden changes that might come about.

Angie Chang: I feel like people come to Girl Geek Dinners oftentimes, they’re often coming from work, they’re very stressed out from their work, and I can see them listening to the speakers and they’re kinda crunching through their head what they have to do, but also taking into account what these women on stage are talking about and thinking through is this the right time to stand up for this or that? Or should I go talk to a recruiter about this really interesting role here? And it’s a constant game of checking in with ourselves, as well where we want to be, and looking at new opportunities.

Sukrutha Bhadouria: How about we end this with a commitment. Like a takeaway. What are each one of us going to do to help us with career transitions. Help ourselves. So I definitely, definitely want to think about is this the role, is this a job that I would chose now? And I wanna commit to this annual review. Keeping time aside every year to think about, is this exactly what I wanna do? What do you think you want to commit to as we end the year?

Angie Chang: I think definitely committing to the asking yourself is this the role that I signed up for originally and where I wanna go from here? Where do I want to see myself in a year? In five years? What is the best case scenario? What is the worst case scenario? What’s a good doable scenario?

Gretchen DeKnikker: I feel like a jerk, but I don’t know that I have a commitment to myself, just because I’ve been literally living in this two year career transition right now of trying to figure out what I want to do next. So I feel like I spend so much time thinking about it, that I don’t know what to commit to.

Sukrutha Bhadouria: I think I struggle with choosing something based off of will it make me happy? Because it’s so vague, for one, and then the other thing is that for me, it’s like exercising. While I’m doing it, I don’t like it. When it’s done, I’m glad I did it. I’m not always loving what I’m doing at that moment. I just learn to enjoy it at some point.

Angie Chang: Thanks for listening to this episode of Girl Geek X podcast. We’ll be back soon with more advice from women in tech and our two cents.

Rachel Jones: This podcast is produced by me, Rachel Jones. To learn more about Girl Geek X, or buy tickets to our next event, visit girlgeek.io. You can also find video and transcripts from the events we went through today. If you’re interested in hosting a Girl Geek Dinner, email sponsors@girlgeek.io.

Angie Chang: This Girl Geek podcast is brought to you by Quantcast. Quantcast specializes in real-time advertising and audience measurement. As the pioneer of direct audience measurement, Quantcast has the most in-depth understanding of digital audiences across the Web, allowing marketers and publishers to make the smartest choices as they buy and sell the most effective targeted advertising on the market. This podcast is also brought to you by Care.com! Spanning child care to senior care, pet care, housekeeping and more, Care.com provides a sweeping array of services for families and caregivers to find, manage and pay for care or find employment and manage their careers. Headquartered in Waltham, Massachusetts, Care.com has offices in Berlin, Austin, and the San Francisco Bay Area.

Angie Chang: You can find video and transcripts from these events at our newly redesigned website. Go check it out, girlgeek.io.



Girl Geek X Podcast Hosts:

Angie Chang

Sukrutha Bhadouria

Gretchen DeKnikker

Rachel Jones


Girl Geek X Podcast Guests:

Arquay Harris, Slack Director Engineering

Kimber Lockhart, One Medical CTO

Malvika Mathur, Quantcast Senior Software Engineer

Dominique Baillet, Care.com Senior Director Growth & Product

Sheila Marcelo, Care.com Founder, Chairwoman & CEO


Girl Geek X Podcast Sponsors:



Episode 1: Mentorship

Resources mentioned in this podcast:

Breaking All the Rules & Finding Your Own Way: Girl Geek X Guidewire Dinner & Panel Discussion

Scaling Sustainably: Girl Geek X AppLovin Dinner & Panel Discussion

Lean in, Geek Out: Girl Geek X SquareTrade Dinner & Panel Discussion


Angie Chang: Hey, it’s the Girl Geek X team you know and love from a decade of over 200 Girl Geek Dinners, hosted at companies like Google, Facebook, Pinterest, Dropbox, Stripe, and many more Silicon Valley startups. I’m Angie Chang, founder of Girl Geek X and one of your hosts for this Girl Geek Podcast.

Sukrutha Bhadouria: Hi. I’m Sukrutha, CTO of Girl Geek X. By day, I’m a senior engineering manager at Salesforce. I’ve worked as an engineer for over a decade now.

Gretchen DeKnikker: I’m Gretchen, COO here at Girl Geek X. I’ve been working in software startups for over 20 years from founding employee to being a founder myself.

Rachel Jones: I’m Rachel, the producer of this podcast. My background is in media and nonprofits so I’m hoping to represent for women outside the tech space still looking for advice in navigating their careers.

Angie Chang: Each week, Girl Geek X puts women on stage at different tech and STEM companies as speakers, role models, and leaders. We’ve been hosting Girl Geek Dinners in the San Francisco Bay Area for a long time and we’ve been hearing from people that they are now less inclined to go to an event after work. Maybe they have kids or a nice hobby like marathon training or regular self care or gym-ing and yet, these women want the content of industry women sharing advice and insights from the trenches, and this Girl Geek X Podcast idea was born.

Sukrutha Bhadouria: When we talk about women at work, we undeniably get a lot of audience questions about mentorship. What we’ve done for our first episode is collected the best of from female executives, engineers, and leaders who have spoken at various dinners this year. Both questions and answers we’ve heard over and over again at dinners, and we’ll tackle those questions for you and give you the cheat sheet.

Rachel Jones: I think the first question that comes up thinking about mentorship is how do I find a mentor? Do you have any thoughts on that?

Angie Chang: The way I look at mentorship is a series of coffee dates with people that may be interesting and asking them for their opinions and sharing my opinion on where I would like to go. By reaching out to people cold, you have probably very low pick up rate, but also people that do say yes will be the ones that see the potential in you and then, have those coffee dates, have those coffee conversations and then, see which of these conversations lead to more conversations and an actual relationship and that can be your mentorship. It’s not going in and saying, “I need a mentor.” It’s going out and asking people for coffee, having good conversations, and more conversations on top of that.

Gretchen DeKnikker: I think when people come and they ask this question at the events over and over again and they’re like, “How do I find a mentor?” I think the underlying question is how do I have an awkward conversation ’cause I think when you’re younger, you have this idea, everyone just says, “Find a mentor, go ask someone.” In my career, I’ve always worked at teeny tiny companies and so, there was never this formal relationship. There were just women that were sort of my heroes and I tried to emulate the parts of them that I really liked and asked them for advice, but I think if you went to any event today and said, “Oh, you mentored Gretchen back in the day,” they’d be like, “Really? ‘Cause I was just sort of answering her stupid questions,” or whatever, but I don’t think it’s as formal as maybe it seems in the beginning and that Angie’s advice is great of just go ask and have coffee and start learning from these women that you admire.

Sukrutha Bhadouria: I’ve been lucky because I’ve worked at mostly larger companies. However, if you don’t learn how to seek out the help you need by identifying the people or the resources you actually need, you’ll never be able to help yourself. Regardless of the programs you might have in the big company that you may or may not be working at, think about what exactly you need, what you want to be, and see who you think of when you think of those attributes that you want to acquire and reach out to them and strike a common balance so that it’s not as uncomfortable and as awkward as you think it needs to be because mentorship in my mind is a two-way beneficial relationship because when I mentor people, I feel I’ve grown so much. I’ve learned so much so I also want to get updates when I’m mentoring someone, how they’re doing and what’s going on with them and it shouldn’t just be that you’ve asked me and set up time and then that’s it, I don’t hear from them.

Gretchen DeKnikker: I think that’s a really good point, too, that when you’re reaching out and you’re asking for coffee to make sure that you’re stating why you want to meet with them, not just like, “Hey, can I pick your brain?” which is a really rude phrase anyway, but be more specific because it’s also flattering when someone asks for your advice, but they’re really specific about why they want it. It’s very hard to say no to that no matter how busy your schedule is.

Sukrutha Bhadouria: Yeah, you want to sign up to be a mentor when you know how you can help someone, right?

Gretchen DeKnikker: Totally, yeah.

Angie Chang: Then after you mentor them for a few years, maybe then you can hire them or have a partnership with them, and they’ll pay off.

Sukrutha Bhadouria: Yeah, absolutely. It’s a cycle. It just never ends.

Angie Chang: It’s a virtuous cycle.

Sukrutha Bhadouria: Yeah.

Gretchen DeKnikker: Rachel, being the youngster in the group, how do you think about mentorship?

Rachel Jones: It’s definitely something that I think that I need. I think the biggest thing about it is having that intentionality and knowing exactly what ways I’m looking to grow through mentorship. I have a lot of different interests and my career path has not been very linear so knowing exactly who’s best to approach and how to approach them is definitely something that I’ve been thinking through a lot. I think having that sense of exactly what I’m looking for before I start trying to reach out and set up those coffee dates is definitely important.

Rachel Jones: This question of how mentor relationships are born came up at our dinner with Guidewire.

Gretchen DeKnikker: I really enjoyed our dinner at Guidewire. The women who were speaking were all super senior. They’d all been at the company for … I think the least amount was 12 years, which was kind of amazing and I think says a lot about the company. In this clip, we hear from Eileen Maier, who’s the Chief Business Officer, Sandia Ren, who’s the VP of Professional Services and Priscilla Hung, who’s the Chief Operating Officer about the advice that they’ve had as they’ve transitioned from mentee to mentor and their perspectives on what makes those relationships valuable and prosper.

Eileen Maier: I think one of the things that’s really important ’cause people say, “Well, you know, I’d like to find a mentor,” and so, “It’s so important to find a mentor,” but I think this is probably the most important thing you need to know is that you actually get chosen. You can ask somebody to be your mentor, but you are going to get chosen. It’s really how do you represent yourself as somebody who’s open? You’re whip smart. Show that you’re whip smart, but recognize that that’s how the relationship is going to happen is that you’re going to get chosen by that person because I think that if we think about people that we’ve mentored, it’s because that connection happened. Make yourself available to those people that you’d like to mentor you and see if you can establish that connection in somebody’s … I guess I’m also saying you have to earn it.

Sandia Ren: We were looking for a manager for the office when we were interviewing, met a number of a number of candidates who had been managing teams for 10, 15 years, built teams from scratch, et cetera, but then we met this woman who … She even called herself a new leader. She’s only been managing team for two and a half years, but as I talked to her, I could just tell that she was really smart, really clued in. She really quickly picked up on the things that we were talking about and she was really excited to learn. She said she wants to switch jobs because she wants to be exposed to more people, different people because she thinks that that’s how she’s going to learn. I could tell the ambition was there and just the openness to learning. Now, I’m like, “How do I hire her?” even though she may not be the best fit for what we’re looking for, but it’s that eagerness to learn, that passion. I think that goes such a long way.

Priscilla Hung: Yeah. I think, for me, it’s the chemistry has to work because I really believe in mentorship because I owe my career to my mentors so I think that when you click, you click. Also, the second thing is just like what Sandia said is you will get a sense that whether the person in front of you actually is open to change. If there’s closeness there, it’s a waste of time.

Angie Chang: I really like Eileen’s point to being open to being chosen and kind of being able to signal to executives or managers that you are ready, hungry for more. I think I definitely have written a lot of emails to people where I [inaudible 00:08:33] things to them, I tried to point out things that I’ve done and kind of opened myself up for new opportunities and projects to get more visibility and hopefully some more assignments and maybe that sponsorship.

Sukrutha Bhadouria: Yeah, a mentor of mine once asked me to think about what I want to be known for and based off of that, I made it known the sort of opportunities that I would want and the universe works together to make it happen if you, like I said earlier, tell enough people that you want something and just knowing what you want to be known for opens you up for opportunities and opens you up for mentors to help you.

Gretchen DeKnikker: I really liked what Priscilla and Sandia had to say about finding someone who was open and who was ready to learn. The women that I end up mentoring, I see something in them. I see a potential in them. I see something really great in them that they don’t see in themselves yet and I really want to get in there and pull that out and help them realize that potential.

Rachel Jones: At our dinner with AppLovin, a few women shared their thoughts on how successful mentor relationships are formed.

Sukrutha Bhadouria: Yeah. The AppLovin-sponsored Girl Geek Dinner was super insightful for all of us and for the attendees. Through their talks, we learned what the panel thought about this whole model of how to make a mentorship relationship successful just based off of how it begins. Alice Guillaume is the Director of Marketing and Katie Jansen is the Chief Marketing Officer at AppLovin and both of them talked about whether or not they thought that mentor relationships are better when put together organically or formed intentionally and they answered this based off of an audience question.

Alice Guillaume: I’ve employed assigning on my team, so I look at kind of like what the needs are and I have paired people together, but I also allow them the flexibility to kind of figure out if it works for them. I tend to think if it’s more natural, it’ll work a little bit better, but at least I’m providing an opportunity to that person to try it. The other thing I’ve tried is just observing. So there are natural kind of relationships that form through time just kind of, that’s just how humans are, and if I see that happening, then I can have that conversation with both parties and see if that would make sense as a match. So I’ve tried both ways. I will say the one where I match it has probably had less chances of working than the organic one, but because there’s not always an organic fit, I still have to give it a try, yeah.

Katie Jansen: Probably like a year and a half ago Adam, who’s our CEO, told me “Go mentor, Helen,” which you might have suspected since I was like “Hello, Helen. You’re not on my team. Would you like to get coffee with me randomly once a month at this scheduled time?” But I’ll be honest, it probably took like about a year ’cause for a while, it felt maybe a little awkward and forced, but I noticed in the past probably five to six months, I’m like okay, like this feels like a real … And we’re both getting something out of it, to your point mentor-mentee relationship. It took a while sometimes I will say with the pairings, but you can hit your stride.

Katie Jansen: And then I have a mentor that I met, it wasn’t at this group (it was at Women in Wireless, and that’s not their name now and I don’t remember their name to be honest with you, they’ve rebranded) but it was a Women in Wireless event, and I was on a panel about mentors, and the EVP of revenue over there was just so impressive to me, and so I afterwards sent her a thank- you note for being on the panel, and then two weeks later followed up with coffee, and now she’s definitely my mentor, and it’s been probably three years – and she’s not in the same vertical as me. She’s in finance and rev ops, which is very different, but I still learn quite a bit from her, but it was almost like, I guess I was courting her or something, but she was open to it so it worked out okay.

Alice Guillaume: Sometimes you have to go get it.

Katie Jansen: Yeah, I know.

Rachel Jones: Have you ever been in a mentor-mentee relationship that was kind of put together intentionally by people?

Sukrutha Bhadouria: I haven’t been put together with someone as a mentee, but I was approached by someone who said, “Please be my mentor,” and I think before that if they had sort of explained to me what they wanted, what their goals were, it would’ve been easier for me to feel less awkward about it. It felt like this huge responsibility without knowing what the expectations are or even knowing where I would contribute. I think with every mentor, everyone wants to figure out where they will contribute and how they will contribute so maybe lead with that first. I think what works best is when it just happens and you make it happen without it being as awkward as it needs to be when you’re specifically saying pairing people up or specifically telling someone that you want them to be your mentor without giving them the background.

Gretchen DeKnikker: I think that’s actually hits on a thing that is the big point that we don’t hear often in the answers at the Girl Geek X Dinners is that you don’t have to go ask somebody. It doesn’t have to be awkward because I think when the question’s being asked, the underlying part of the question is, “How do I go do this in a way that’s not awkward? Do you have some advice?” I think that’s the part that, maybe the myth that we want to dispel today.

Sukrutha Bhadouria: Yeah, totally.

Angie Chang: I’ve had a few experiences with mentorship. I’ve participated in a program that connects women as mentors. I mentored somebody who was a sales engineer. It wasn’t a very clear fit to me as to why we were paired together and I think at the end of the day, it was the lack of communication from both sides due to our busy schedules that led to a not probably ideal mentorship situation. I also ran the mentorship program at Hackbright Academy where for over four years, we had connected every quarter three working software engineers with one engineering fellow to be mentored, and I think watching that program happen, it made me realize that mentorship is kind of a hit or miss situation about maybe 50% of the time and that you have to continue to mentor not just once and twice, but continue to do it maybe like twice a year and kind of try out different bits because not every pair is going to be ideal.

Angie Chang: We can probably go on and on about whether organic or nonorganic mentorships work. I think the bottom line is to keep trying and some matches will work and some won’t, but in the meantime, we have had a speaker, Claire Hough, who is a strong engineering leader, most recently, the Senior Vice President of Engineering at Udemy speak at the SquareTrade Girl Geek Dinner about engineering leadership and how your job is to grow your team and their output. Basically, she gives great advice about how to balance mentoring others with your own growth.

Claire Hough: I think as an engineer, I think first chance that you get at showing some leadership is how you mentor your more junior engineers. You’re still keeping up your technical skills because you’re still doing your technical work, but you’re reviewing somebody else’s work and giving them advice or giving them good feedback on how they’re approaching problems and all that. I think that kind of builds your skills alongside your technical skills. Then your mentoring skills become like you’re mentoring one engineer, you’re mentoring the next engineer and then, you’re kind of building that and as you take on those mentoring skills and time to mentor, then you are going to do less technical work over time, but that doesn’t mean that you’re not keeping up with technology.

Claire Hough: At some point, you may have a big team such that you cannot keep up with every single thing that everybody’s doing. That’s when you have to kind of let go and trust other people that they know what they’re doing. I think I always tell the first time managers that your success is not about you. It’s about your team. The output that you should measure yourself is output of your whole team as well as the growth of your whole team. You have to at some point change that, change how you’re looking at yourself, but I think there’s a lot of satisfaction in mentoring others. Enjoy that while that’s happening and don’t worry about, whatever, the 20% of time I’m spending mentoring others is somehow it’s taking away from me. It’s not. It’s adding to who you are as an engineer by giving that feedback.

Rachel Jones: You all have shared a lot of your experiences being mentors. When you’re in that space, how would you say you balance that with your own growth as a professional when you’re investing in someone else?

Gretchen DeKnikker: I feel like mentoring at this time and how much time I would invest in it has a lot to do with how I’m growing as person, too. You sort of transition in your career from a point where you’re learning skills to where you’re developing people, and I feel like as you have mentors, they help you grow as a person also, the same way that your team when you’re managing, helps you grow as a leader. The time that I spend with these women is inspiring and it gives me a lot of motivation, and it’s always worth my time because they wouldn’t be people I spent time with regularly if I didn’t feel like we were both getting something out of it.

Angie Chang: 100 sign.

Gretchen DeKnikker: You can’t put emojis?

Angie Chang: One hundred emoji.

Rachel Jones: Do you feel like there was a specific point in your career where you felt like you transitioned from being a mentee to being a mentor?

Sukrutha Bhadouria: I do remember when I was looking to move into management and I was taking all this advice from all these great leaders that I would find at work and outside of work, and the minute I became a manager, I had to realize that wait, a minute, now I’ve signed up to be a mentor to my team and I thought I had to have all the answers right away, but I think that’s the part of the learning while I was a first time manager, I was learning how to be a better mentor and in turn, I was learning how to be better at my job.

Gretchen DeKnikker: I don’t think there’s a point where I feel like I transitioned. I’m still both. There’s still women that I learn from and I admire, and I want to spend time with because they can help me understand things in a way that I don’t understand them yet. I think the one realization I had more recently, not just from like, “Oh, my I’m being a mentor now,” but that I set an example whether I want to or not. There’s a woman that worked in … we shared an office with another company and she came up to me one day and she’s like, “Look, I got a tattoo on my wrist because I figured if you can be a badass boss with a tattoo then I can be a badass boss with a tattoo.”

Gretchen DeKnikker: I kind of freaked out a little bit and then I realized oh, she’s not like doing that because I’m doing it. I’m not setting this weird example. She didn’t need to come consult with me on whether or not having a tattoo is a good idea, which I would’ve said yes, do whatever you want, but it was this thing of whether I’m paying attention or not, I’m setting an example and that maybe I want to be a little bit more careful, except for the tattoos, which I’m going to rock until my skin’s too saggy.

Angie Chang: Admittedly, I feel like I constantly think that I should be mentoring people more and that’s something I’m definitely looking to develop in the next year or two is identifying more people to mentor. I think that will also accelerate my growth.

Gretchen DeKnikker: I think it’s worth saying, too, that you outgrow some of your mentors. Earlier in my career, it was like, “I want to be her.” Now I am her. There were certain things in this woman where she would get recruited by investors to come in and be a part of a startup, and I was like, “I want that to be me one day.” Now that is me. She still has a lot of great advice for me and I’m still in touch with her a lot, but as far as what I need for the next level, she’s not that person anymore.

Sukrutha Bhadouria: She’s now one of your mentors, but she’s not the main source of …

Gretchen DeKnikker: Yeah.

Sukrutha Bhadouria: … information to get to the level that you thought you needed to be.

Gretchen DeKnikker: Yeah. We’re dating. We didn’t get married. Right?

Sukrutha Bhadouria: Right.

Gretchen DeKnikker: It’s not a lifetime commitment. We don’t celebrate anniversaries, yeah.

Rachel Jones: This conversation has definitely got me thinking about how I should be identifying more mentees in my life to reach out to and learn from as well as provide some guidance. It’s a really great conversation.

Gretchen DeKnikker: I think I’ve–now thinking, “I need to have more mentors in my life. I need to go connect with the women that inspire me.”

Sukrutha Bhadouria: It’s so funny I was thinking about how I need more. I want to have more mentors. I want to have more mentees. It’s just the whole experience is so enriching and the good thing about Girl Geek Dinners is we see these amazing women speaking and through that, too, we’re indirectly getting inspiration and motivation, and we’re getting a chance to meet this amazing community of women and so there’s clearly not a shortage.

Rachel Jones: Yeah, I think this has been good to hear, especially just talking about how these relationships are formed because I’ve definitely been hearing, “Oh, you need to find a mentor. You need to find a mentor,” but I think just connecting with people and seeing what happens organically could be a better way to approach it than just identifying someone and saying, “You are my mentor. Let’s make this happen.” It’s been good to hear.

Angie Chang: Thanks for listening to this first episode of the Girl Geek X Podcast. We’ll be back soon with more advice from women in tech.

Rachel Jones: This podcast is produced by me, Rachel Jones. To learn more about Girl Geek X or buy tickets to our next dinner, visit girlgeek.io. You can also find full videos and transcripts from the events we discussed today. If you’re interested in hosting your Girl Geek Dinner, email sponsors@girlgeek.io.

Angie Chang: This Girl Geek Podcast is brought to you by Guidewire – Guidewire software provides for backend system software to the global property, casual and workers’ compensation insurance industry. Also, AppLovin – AppLovin is the platform that gives game developers the ability to market, grow, and finance their businesses. And SquareTrade – SquareTrade is a top rated protection plan trusted by millions of happy customers and offered by top retailers.


Girl Geek X Podcast Hosts:

Angie Chang

Sukrutha Bhadouria

Gretchen DeKnikker

Rachel Jones

Girl Geek X Podcast Guests:

Eileen Maier, Guidewire CBO

Sandia Ren, Guidewire VP

Priscilla Hung, Guidewire COO

Alice Guillaume, AppLovin Director Marketing

Helen Wu, AppLovin Senior Director Growth Partnerships

Katie Jansen, AppLovin CMO

Claire Hough, Apollo VP Engineering

Girl Geek X Podcast Sponsors:




Breaking All The Rules & Finding Your Own Way: Girl Geek X Guidewire Panel (Video + Transcript)

Like what you see here? Our mission-aligned Girl Geek X partners are hiring!

Guidewire girl geeks: Priscilla Hung (Chief Operating Officer), Eileen Maier (Chief Business Officer), Lerk-Ling Chang (VP of Strategic Ventures), Sandia Ren (VP of Professional Services), Roopal Shah (VP of Go To Market Delivery) at the Girl Geek X Dinner held at Guidewire’s offices in Foster City, California.

Roopal Shah / VP, Marketing / Guidewire
Priscilla Hung / COO / Guidewire
Eileen Maier / CBO / Guidewire
Lerk-Ling Chang / VP of Strategic Ventures / Guidewire
Sandia Ren / VP, Professional Services / Guidewire

Transcript of Guidewire Girl Geek Dinner – Panel:

Roopal Shah: All right. Welcome everybody. We are so glad that you guys are here. My name is Roopal Shah. I’m the Vice President for Go To Market Delivery, which essentially is product marketing, sales enablement, business planning, and operations for our Go To Market functions. I’ve been with Guidewire for eight years. That hopefully tells you a little bit about what an awesome place this is to work at. Without further ado I would love to have each one of these ladies introduce themselves, tell us a little bit about what your role is, who you are, and how long you’ve been at Guidewire.

Priscilla Hung: Welcome, everybody, to Guidewire. My name is Priscilla Hung. I’m the Chief Operating Officer of the company. I have been with Guidewire for 13 years and two months. In Silicon Valley, that’s 1,300 years, as you know. I’ve been working in the Valley for about 30 years. This is, by far, the best company I’ve ever worked for. It shows because I’ve been here forever.

Priscilla Hung: My responsibility from a day-to-day basis, basically, is to make sure that the operation work, by design, but my direct responsibilities today include corporate strategy. That includes all the business development, market strategy, M&A, partners, product marketing, Roopal and Eileen’s team, and whatever that entails, including film marketing and definition of the market and product development. What else?

Eileen Maier: Film.

Priscilla Hung: Yeah. Yeah. I did alliances.

Eileen Maier: Influencing.

Priscilla Hung: Influence, like all the IT, IS, and security, cloud operations, customer success. I think that’s it. I really love the company. I love everybody here. I’m so delighted to see so many old faces here. I’m looking forward to have some conversation with you tonight.

Eileen Maier: Hi, everybody. My name is Eileen Maier. I am the chief business officer at Guidewire. I’ve been here 13 years. Today is my 13th anniversary! <clapping> I know! My role is chief business officer; I work for Priscilla. First things first, I do whatever she wants me to, but I’m privileged to lead the team that is actually the voice of the market. In understanding, you saw one of our customers talking about their market needs and what is it that they need to run their business. I have a team that is responsible for really understanding where those market needs are and to translate those into business opportunities for Guidewire. Where do we see a market opportunity by serving that customer’s needs?

Eileen Maier: Then, they work very closely with another member of Priscilla’s team, the product team, to realize that, to make it into something that we can bring to market. Then, I’m also privileged to have Roopal on my team because then it’s her team that does the Go To Market Delivery, so how do we translate that product or that solution into something that our sales people can sell so we can grow our business?

Eileen Maier: It’s been exciting and a wonderful journey to be with Guidewire. This is a relatively new position. I’ve been in it for about a year. I think that that’s something that I’d loved the chance to talk to you about, of transitions within your own company and how you can grow your career without having to change where you work. Okay. Over to you.

Lerk-Ling Chang: Hello, everyone. Can guys hear me? Is my mic working?

Roopal Shah: Yes.

Lerk-Ling Chang: Okay. Awesome. Okay. I’m Lerk-Ling Chang. I’m VP of Strategic Ventures here at Guidewire. My focus is on helping the company grow through acquisitions, through partnerships, and through venture investments. I’ve been with the company now for 16 years. That’s 14 years more than what I thought I would be here, so it does speak to the character of the company and what we love about the company. Encourage you guys to talk to the folks here who are wearing Guidewire t-shirts. Feel free to ask them why are you here and would love to share that with you.

Lerk-Ling Chang: I joined the company when the company was really small, 12 people, the company had just landed the first customer. Had just raised a first round of funding but didn’t have a product yet. They needed a product manager. I worked in one of the six co-founders at Ariba, a previous company where person that I worked at as well. He reached out to me and said, “Hey, would you like to join this startup of mine?” I was kind of in the middle of a transition. I ended up joining. Ken and I product managed the first product. Actually, I worked with Sandia on that one. A couple years later, led up the development of a second product, PolicyCenter. It’s been an exciting journey.

Lerk-Ling Chang: Now, I’m focused primarily on acquisitions, partnerships. Then, in the last few months, I’ve picked up the lead for our venture investments.

Sandia Ren: Hi, everyone. Is my mic on?

Roopal Shah: Mm-hmm (negative). No.

Sandia Ren: Hi. I’m Sandia Ren, and I’m a vice president on our professional services team. We’re the team that goes out to customer sites and helps them implement our product and use our products. We’re the ones who get to travel. I’ve been with Guidewire for fifteen and a half years, so a little less than Lerk-Ling. I actually started as a software engineer. Yes, she was my product manager. I wrote unit tests for our very first product. Now, I’m Vice President of Professional Services. I would love to tell you about that journey. I’ve been very grateful to Guidewire for the opportunities that I’ve had.

Sandia Ren: These days, I look after our specialized consulting teams. These are the teams that work on our products outside of our core systems. This includes our data and analytics products, our digital products, underwriting management, and then competencies like upgrades and testing and infrastructure, all the stuff that people don’t like to think about so that’s in there, the specialized umbrella.

Sandia Ren speaking at Guidewire Girl Geek Dinner.

Sandia Ren: Then, I also look after what we call the Guidewire Services Center. These are our delivery centers around the world that have lots of teams of consultants who help our customers implement and deliver our products remotely. We have four offices now. Our largest is in Dublin, Ireland. Then, we have a team in Pennsylvania. It’s our US team. Then, we also have a team in Madrid, Spain. Then, we just opened an office in Malaysia.

Sandia Ren: For full disclosure, I just got off the plane from Malaysia. If it sounds like I can’t get my words out, that’s my excuse for tonight but I do certainly feel very privileged that it’s my job to travel around and meet just exceptional people around the world who all share our values and are committed to the same goals and our customers. Thank you so much for coming. It’s really exciting to be here.

Roopal Shah: Okay. Awesome. Thank you for that.

Roopal Shah:Let’s start with our first question and this is to all of you. I would love to get your perspective on insurance, specifically there’s a lot of talk about insure tech and what a pivotal time this is right now. What are your thoughts on that? Do you think it’s a pivotal time and what sort of skill sets do you think insurers and insurer tech companies are looking for right now? Anybody want to take that?

Eileen Maier: I can’t speak unless you give me your mic.

Roopal Shah: There you go.

Eileen Maier: I now have control. To rephrase the question, is this an exciting time in insurance? I would say, “Absolutely.” We serve the insurance industry. We are an insurer tech. Within the walls of Guidewire, I’m just so excited because every day, I get to talk about innovation.

Eileen Maier: When I started 13 years ago, today, anniversary, innovation really meant can I improve my business processes? Can I innovate on how I do my business and run my core systems better? That’s still true today. You can see the benefits from that video that we looked at not too long ago but innovation is transforming the industry. When you look around a disruption, it is absolutely impacting the insurance industry. It’s disrupting the way that they sell their products because people are expecting a mobile experience. They really don’t want to buy insurance through a broker. They actually don’t really even understand it. People are looking for insurance actually more associated with the service.

Eileen Maier: I’m sure everybody here is an Uber user. Not too long ago, I got an email in my inbox from an Uber saying, “Hey, with your app, you can rent a car now.” Actually I’m going to rent the car. I’m not even going to think about insurance because insurance is bundled in with that service. We’re thinking every day about what’s disrupting and transforming the industry because we don’t want to deliver products that they just need today. Certainly, we’re doing that. We want to think about what are the products that they need to deliver in the future?

Eileen Maier: I think that if, going back to the second part of your question, what are insurers looking for? They’re looking for creativity. They’re looking for innovation themselves. They’re looking for ways to do things differently because they really don’t want to just continue to do what they’re doing today.

Eileen Maier: Okay. Anybody else want to take a swing at that?

Lerk-Ling Chang: Yeah. I can chime in. I think people can hear me. Insurance is really changing really quickly. In the last five years, it’s probably changed … If you talk to anybody in the industry, they feel like the change has really come at a much faster pace than ever before.

Lerk-Ling Chang: It’s really driven by three things. Eileen talked about some of the things that are coming from consumers. You and I, we all want different things from our insurance companies than we ever did before but it’s also coming from the insurance companies themselves.

Lerk-Ling Chang: I remember 15 years ago, going onto the first customer visit and seeing people still using mainframe systems. It’s shocking but that’s actually a very common system that people still use. When insurance companies are still using that, they can’t actually deliver the kind of service they need to. It’s not because they don’t want to. They’re just stopped by doing that. In that sense, it’s really an exciting time for companies like Guidewire, who have solutions that can help insurance companies provide better service to their customers. That’s been a lot of also additional investment into the industry that then, at least … In the P&C, Property and Casualty technology space, in last year, for example, there’s been a billion dollars of venture funding that have gone into the space. That’s been a lot of startups. We’ve been the beneficiary of that, being one of the leaders here.

Lerk-Ling Chang: The industry has seen a lot of change and insurers themselves are looking for new solutions. It’s one of the best times to be in the industry right now.

Sandia Ren: I thought I’d address your question about what I personally think about insurance. I’ll be honest. When I started 15 years ago, I just followed good people to Guidewire. I didn’t really think too much about the domain or even the product that we were working on, but over the last 15 and a half years, I’ve definitely developed a true, very strong appreciation for what insurers try to do. It’s been amazing to see it evolve over the years but certainly we’ve seen a lot more when it comes to natural disasters.

Sandia Ren: I’m from Houston. We went through Harvey last year. That really hit home when I was hearing my neighbors and that was all that the talk was about in the neighborhood. It was claims and all these terms that I understood. When being in professional services, what I love about it is I get to go out and I get to meet with our customers and understand their business goals. Their business goals are about how to help people like you and me when we’re in our biggest time of need. That’s pretty awesome.

Sandia Ren: In the beginning, we used to say, “Well, insurance isn’t glamorous,” and whatever. We didn’t talk about it too much, but actually I think insurance is awesome. It’s really meaningful. I just wanted to share that perspective because I don’t think it’s something that you really realize until you think about it. At least, it was for me.

Eileen Maier: I actually wouldn’t mind building on that because it’s also the industry itself has changed. One of the more recent acquisitions, the most recent acquisition that Guidewire made was with a company called Cyence. It really is representative of how the insurance industry has shifted because 13 years ago, there wasn’t the need for something called cyber insurance or cyber risk but now there certainly is. Innovation and technology has driven, they actually created a new risk for us.

Eileen Maier: This is really incredible because what Cyence does is they have created a data engine that allows them to sweep up massive amounts of data so that they can use algorithms, detect where cyber risk is. This is completely different type of insurance than the property and casualty insurance that you use to insure your car.

Eileen Maier: I think that there’s this dynamic change within the industry itself because what is an insurable risk or what is risk itself is changing, which means the needs of consumers or businesses is changing and the market has to keep pace with that. The times around us ourselves is actually making it a dynamic time for the industry.

Priscilla Hung: Yeah so maybe I just really briefly round out. I think the ladies will touch on a lot of points already, pretty complete but just a few words. I echo Sandia’s sentiment. When I joined Guidewire 2005 and I joined 100% because of the founders. I’ve known four of them from my previous job. I had no idea what insurance industry is. In fact, when Marcus, our CEO co-founder call me and say, “Come join us,” I was like, “Why do I want to work for a company that serve the insurance industry?” All I thought about is I have to write money to them and when I have a crash, that it takes them a long time to pay me.

Priscilla Hung: But it’s a little bit of a learning curve for me but very, very quickly I have completely falling in love with this industry because you got a preview of some of the videos that you’ve seen but genuinely, our customer, the insurance carriers, they are generally full of people that spend a life and their career in making people whole. They are learning every day and trying to respond to the market and is an inflection point because it’s only very recently that all of us spend all our waking moments looking at devices.

Priscilla Hung: This morning on Today … I don’t know whether you guys watch morning television. I live by them. It’s one of the morning news. It says that an average person I believe is an adult. It didn’t say age group. It says that it spent on the average of 11 hours on electronic devices and between the age of 50 and 65, 13 hours. I don’t know how many hours people sleep but imagine that you spend so much time.

Priscilla Hung speaking at Guidewire Girl Geek Dinner.

Priscilla Hung: People don’t talk to each other anymore. My husband and I were texting each other the other day. I was like, “We have to stop this.” What the insurance company is trying to do is they want to understand this pattern. They want to understand how you live now because in the past, older people like me buy insurance, they call an agent and they’re all, “You fill in the form,” but nobody talk to people anymore. Most of you don’t have a landline. It is to response to the market, respond to this really rapid change because of what technology has come to play. I’m really proud to be part of this team and provide enabling technology for these insurance carriers to respond to your needs.

Roopal Shah: Awesome. Is my mic on? Can you guys hear me? Oh! There we go. All right. Okay. Let’s switch topics a little bit and talk about careers. What I would love for each of you to tell us a little bit about your career progression, how you got to here, if you made any calculated moves, if you had sponsors, mentors, just tell us a little bit about your journey to where you are?

Priscilla Hung: Me first? Okay, sure. My career journey. You might expect me to say, “Oh, you know, you must plan, you degree that you study and you plan your steps.” Absolutely negative. In fact, I go completely opposite side. For those of you who were raised by Asian parents, I’m sure that you appreciate what I’m talking about. My parents wanted me to be a doctor or a lawyer or a doctor or a lawyer, but especially I was pretty good at my grades when I was young and whatnot but I’m terrified of blood. My grandmother said, “Don’t be a lawyer because you will have to represent bad people.”

Priscilla Hung: Any case, so those path are gone. I said, “Meeny meeny meeny moe. So, what I do?” I ended up picking an engineering degree. It’s actually by elimination as opposed to plan. If you really asked me what I wanted to study, I want to be artist. I was a trained ballerina. I play pianos. I was a performer. I wanted to be artist. My parents are, “No, no, no, no, no.” You know how it goes.

Priscilla Hung: I got a degree that I really didn’t want to go for. Then, it’s like I go for a job now. I really stumble into … I finished my degree in the East Coast. I came over here because of a boyfriend. Two months later we ended. That was like, “Okay. All right. I need to look for a job.”

Priscilla Hung: It really, completely out of the blue, I got a call from a friend from high school who worked for Oracle. Oracle, at the time, in 1989, was a very tiny company. They were not in the Redwood Shores, up on Belmont Hills and said, “Come work for Oracle.” I was like, “Why to work for a database company?”

Priscilla Hung: I went through an interview that basically, in hindsight, if I were interviewing me when I was back in 1989, there is zero chance I will offer this girl a job because the interviewer asked me … I’m sorry. Am I running out of time? It’s a pretty long story. It basically is saying that, “So what would you like to do? You have an engineering degree. Would you like to be an engineer?” “Absolutely not.” I was like, “Okay. So, what do you want to do? Do want to be marketing?” “What is marketing do?” Show you how it goes. I thought, “Okay. You got good grades. You know, I’m going to hire you.” That’s when I started in 1989 at Oracle.

Priscilla Hung: In fact, I hop many, many jobs in the first 10 years because I actually didn’t really want to be in the discipline. I want to be an artist, remember? I hop around. I didn’t have a compass but I was fortunate in my career in the last 30 years that I ran into two people, both of them are my manager. Both of them saw that I’m someone that could be cultivated. I followed my first manager to three jobs. I finally, many jobs later, I landed at Ariba.

Priscilla Hung: I met someone that really wanted to develop me. He hired a professional mentor for me. The professional mentor was a retired woman executive. She completely changed my life. She completely utterly changed my life by basically putting a program together, told me five things I need to change, including my voice. “Don’t squeak like this. Don’t talk like a girl, so you have to talk with a certain voice.” This is my work voice. The second thing is, you won’t believe this, is that you smile too much. Stop smiling. I was like, “Stop smiling.” It actually took me a long time to really understand why do I need to stop smiling?

Priscilla Hung: The third thing is when you’re in meetings, talk at least once, speak at least once. Don’t go to a meeting and be in complete silence because if you are complete silence, you become irrelevant. Even if you’re repeating what other people are saying, paraphrasing it. Just speak once, and how you dress, how you present yourself. Now, I forgot what the fifth thing is but it’s five things.

Eileen Maier: Write things down.

Priscilla Hung: Yeah. Sure. Yeah. Yeah. Those things really completely changed my life. I would have to say that my career really started to go somewhere after I practice what my mentor told me. Add, after Ariba, four of the founders actually came from Ariba. Is again because of people I join here. The opportunity that the founders created for me. I got an opportunity to talk, do a lot of things that I have absolutely no experience, zero experience. It’s not planned for. It’s not because I’m experienced. It’s all because you have a new problem to solve. I work very, very hard. I focus on what I need to do, drive outcomes and then, one good outcome lead to another good outcome.

Priscilla Hung: Also, in hindsight, because all the randomness, all the different flopping around. My career actually helped my current job today because right now, I have a pretty wide scope of responsibility. Many of those jobs I actually have done in the past, not because I planned it. I would just say that I didn’t go through the traditional way. I didn’t plan but it worked out. I think it’s because of people that honestly is people relationship I built and people that help me along the way.

Eileen Maier: Okay. Are you sure you’re done? I’m going to start my story differently but then I think you’re going to find some similarities between my story and Priscilla’s story. Wasn’t an artist but also wasn’t an engineer. I got an English degree. I remember telling my father that I wanted to move from accounting to English. That was a pretty difficult conversation, at least for me. He took it pretty well, but it was, when you get out of college and you have a Bachelor of Arts in English, you do struggle a little bit to say, “Where am I going to get a job?”

Eileen Maier speaking at Guidewire Girl Geek Dinner.

Eileen Maier: This is where I think this theme of two pieces of advice. Be curious and also be open to luck. I think my parents felt a little bit sorry for me. I’m trolling around, living upstairs. They’re like, “You need a job.” Again, be open to luck. Take advantage of favors.

Eileen Maier: I got an interview with an insurance company. Really, if you’re an English major in Liberal Arts, actually insurance is a place that will consider. That’s how I entered into the insurance industry. Then, the curiosity kicked in because I was curious about, “Well, what it like to be an underwriter?” I had no idea. Learned that trade. Also saw what other opportunities were available for me within that insurance company. It was Liberty Mutual Insurance.

Eileen Maier: I was living in Philadelphia. I got the opportunity to move up to Boston. I took a role in a training organization. Again, within the same organization exploring different opportunities, different interests. I really started to learn something about myself by trying different things, by being curious. Through that, I got an opportunity to go into risk management. I joined a consulting group. That required me to get an MBA. It’s like these things start to build on each other and you follow a path. There’s something that you do when you get your MBA and you’ve worked for an insurance company for 10 years. You quit and you get another job.

Eileen Maier: That’s when I left and I moved to PeopleSoft. This is where I entered into technology but, again, being open to luck, why PeopleSoft? How could they possibly even consider me? It’s because somebody I went to grad school with. I called her up because I just wanted to get some advice from her. I wanted to understand how she made a career transition.

Eileen Maier: By reaching out and having a learning conversation, she actually wagged her finger at me and said, “I know exactly what you need to do.” We all want somebody to say, “I know exactly what you need to do. Give me the answer,” but she was right. She turned me on to this profession I’d never even heard of. It was called sales consulting or sales engineering. It’s where you have this opportunity to help customers, you’re consulting with customers, you’re understanding what is the business problem that they’re trying to solve. Then, you say, “Oh, well. I have just the thing for you.” Then, you go into a product demonstration and you show them how this product that you have can change their life and transform their world. It’s a little bit of performance. It’s a little bit of teaching. It’s a whole lot of consulting. It requires a lot of courage and empathy. I loved that.

Eileen Maier: I worked at PeopleSoft for quite a number of years. We got acquired by Oracle. I went on that journey too but it was within a couple months that I moved out to the West Coast, another similarity, poor guy. Within two months of being out here, my phone rings. It’s somebody again that I used to work with. He had just joined Guidewire. He said, “Eileen, they’re starting this team. It’s really cool. I’ve met the founders. They’re doing something very different. It feels like PeopleSoft,” because that was a bit of a culture, a cult. He said, “But there is one thing you need to know. Mmm, they serve the property and casualty insurance industry.” He’s pitching that to me like you’re going to have to deal with that. I was like, “David, there’s something you don’t know about me.”

Eileen Maier: With Guidewire, it was bringing together 10 years at Liberty Mutual Insurance, a number of years. I won’t give it to you because then you can figure out my age, at PeopleSoft in technology. Then, I joined here in 2005 and worked with Lerk-Ling because it was PolicyCenter, the second product that I was able to go out and start to build the sales consulting organization.

Eileen Maier: Then, with so many of the opportunities, the same thing that Priscilla has spoken about and you’ll hear Lerk-Ling speak about it and Sandia as well is that just in a growing organization, there’s so many things that need to be done. You start building a sales consulting team. Then, you start building a global sales consulting team. Then, you realize we really need a demo team infrastructure so we need to build that. Then, we really need to enable our sellers better as we’re starting to scale the organization so you start to build that.

Eileen Maier: With a mission and a vision, you start to collect really good people around you. I’m so privileged. I’m humbled by the people that I work with. It really is this journey of curiosity but also being open to luck and go into learning conversations, curious to find out what you might hear but also be transparent with what you’re looking for because you might be really surprised. Somebody might be able to wag their finger at you and say, “I know exactly what you need to do.” Anyway, that’s my story.

Lerk-Ling Chang: We haven’t planned this, but my career, it merged there, was not planned. I didn’t set out to work in a software company. In fact, I didn’t even know that was there was such a thing called software product management. Graduating from college, I had an economics degree. Coming out of college, the two positions that people recruited for was investment banking and management consulting. I picked the one that I thought was most interesting, which was investment banking. Did that for three years. Went to business school. Didn’t hear about product management either. Didn’t want to do investment banking, so decided to do finance. Eventually decided that was not my track. When I moved out to California, I talked a business school friend.

Eileen Maier: Was it for a guy?

Lerk-Ling Chang: It was not for a guy. I was already married, so not for a guy but it was through a business school friend who was working for the startup in Mountain View. I had no idea what a software company was, no idea what even development looked like in a professional enterprise. He just said, “Hey! Why don’t you join this software startup? Got this cool health care tech, monitoring health system,” called Health Buddy. It’s like this cool, little system. “They needed someone to help them with product partnerships. Why don’t you come join? You have investment banking. They’re going to need help us figure out how to put deals together.” I was like, “Okay. Great. Let’s go figure it out.” Anyway, I joined. Pretty soon after, I realized the product was not quite ready for any partnerships of any kind. It needed a lot more work in order to support and not any partner of any sort.

Lerk-Ling Chang: Then, I started talking with the product team and said, “Hey, you know, it needs this, this, and this.” There was only one product manager, who was completely overwhelmed with work. He wasn’t going to have any time to do it. I just ended up deciding to write up all the requirements that I thought would be needed for the product. I didn’t know this was product management. I just started writing out learning requirements, step-by-step flow of what I thought someone would need. Then, just started socializing it with the head of the product team. This guy said, “Hey! Do you want a job? Do you want to be our second product manager?” That’s how I fell into product management. I did that for a bit.

Lerk-Ling Chang: Then, got a job at Ariba after that, where I ended up working with Ken Branson, who is one of the six co-founders here. That’s how I end up here at Guidewire. I did product management at Guidewire for, I guess, it’s probably about 12 years. Then, decided to switch out of that role into something completely different, focusing on corporate strategy.

Lerk-Ling Chang: What that means initially was two things, strategic partnerships and then second is acquisitions. It’s been fun doing that because I worked on acquisitions as an investment banker before, but, at that time, you run numbers. You say, “Hey! You can cut cost here. You can add here. You can the increased revenues by 10% 20%,” but you don’t really know what it looks like.

Lerk-Ling Chang: Now, I’m on the other side of the table where we have to go through systematically to understand, “Hey, can we really grow revenues, work with all the different teams around a company to understand how to plan an integration and make sure the acquisition actually comes to fruition?”

Lerk-Ling Chang: I’ve been involved in all of the five acquisitions that we’ve done. It’s been a really interesting experience seeing that. Now, I’ve had the opportunity as part of this to now lead up our venture investments, which are going to be starting out and doing a lot more of.

Lerk-Ling Chang: It mirrors the careers of these two ladies here. It’s not planned at all, taking the opportunity, taking the initiative when you see something that’s a problem that you think you can help fix, taking the initiative to suggest solutions, and then working with people to see if that can actually come to fruition. That has helped quite a bit.

Lerk-Ling Chang: But the other thing, too, is finding people along the way that have helped me. For example, Ken was instrumental in bringing me here but even in my first job in investment banking, I had a senior managing director who I was able to work really closely with. She let me run a bunch of her deals, which is pretty unusual coming out of college.

Lerk-Ling Chang: Then, now I get to work with Priscilla and Eileen. You get different opportunities and you find people who can help support you and give you new things to do.

Sandia Ren: Okay. Going to be the same themes. Tells you something about Guidewire, but I remember looking recently at my high school yearbook. It has the question like, “Where you going to be in 10 or 20 years,” or something like that. I said I was going to be an electrical engineer and I was going to have two kids. That’s totally wrong. I am past 20 years so you can figure out how old I am but I have a three year old, and I’m not an electrical engineer.

Sandia Ren: Certainly my life didn’t quite turn out the way that I thought it would be, but I did start out on that path. I did get a computer science degree out on the East Coast. Then, I came to California. I actually followed the gold rush because that was during the dot-com boom, but I caught the tail end.

Sandia Ren: When I joined the company that I joined, I think the stock price was at 200. When I got the offer, it was 200. When I actually started, it was like 20. I caught the end so I had to work.

Sandia Ren: Anyway, actually and it’s all about people connections, too. The reason that I actually ended up at that company was because of somebody named Charlie Lee, which some of you guys know from the industry. He invented Litecoin and all of that stuff. But Charlie and I were in school together. He said, “Hey, I interviewed for this great company. You should really come and meet with them.”

Sandia Ren: I met with them and my hiring manager turned out to be the future CTO of Guidewire. I worked with him and had fantastic mentors there who taught me how to be an engineer. I think in school, you learn how to code but that’s pretty much it. I had a mentor who taught me how to work with the requirements, not to just build whatever was given to you but take a step back, understand why and make sure that you feel like this is the right way forward. I don’t think that’s something you learn in school. Just the start of learning from many wonderful mentors along the way.

Sandia Ren: Anyways, really, it’s when one door closes, a window opens. As was happening often there, the development at the company that I was at because they had gone from 200 to 20. The team was getting smaller and smaller. They eventually decided to outsource everybody to India. I was told that I had six months left.

Sandia Ren: I kid you not. That very day I had lunch with former co-workers who had left. They said, “Hey, Guidewire is hiring. Are you interested in coming to meet with us?” Sure. It was my old team, my old hiring manager and all of my great mentors who were over there. That’s how I ended up at Guidewire. Like I said, I wrote unit tests for our very first version of our product.

Sandia Ren: Then, I was a software developer for a while. I thought, “Yeah. This is the path I’m going to do,” but that lasted probably just for three or four years. That was when I started thinking, “Do I want to do something different?” I got enough…it was starting to feel a little routine, so thought maybe a different industry, maybe just needed a change. I actually started looking outside of Guidewire.

Sandia Ren: Then, I remember what pretty much changed my life, it was an email. Again, full disclosure. I am a huge Red Sox fan, being from Boston, so huge Red Sox fan. The year was 2004 and our Liberty Mutual had just gone live with our first product. Our head of professional services said, “They’re so excited. They’re as excited about the go live as the Red Sox winning the World Series for the first time in 89 years,” which is impossible but that’s what he said.

Sandia Ren: A light bulb went off in my head that, “Hey., maybe I can stay at Guidewire but do something different here. Maybe I can move into the services team and it would also give me the opportunity to move back to Boston,” which is what I had been hoping to do.

Sandia Ren: At that time, we were still pretty small. It was 2005. I went to Ken, and I said, “I have this really crazy idea.” I told him about it. Actually, I was working on PolicyCenter then. He said, “You know, it’s not a bad idea. You built PolicyCenter, so you can go implement PolicyCenter when we sell it.”

Sandia Ren: I learned really quickly how hard that was. Lots of lessons learned there, but he was really open to it. Again, just I think that is just a leadership style that I want to emulate. It’s being open to people’s ideas. I really appreciate it he didn’t say, “You know, that’s crazy.”

Sandia Ren: That really kicked things off. I found that consulting professional services worked really well for me because I really like to understand the business side. But I still got to use my technical skills in helping our customers come up with solutions that would work for them.

Sandia Ren: Then, from there on just within Guidewire, I was open to opportunities. I had managers who had crazy ideas, too, and for whatever reason would let me help them implement it. I think there are many times throughout my career where I was given a role that we could have easily hired for externally and would have found somebody who had been doing it for 10, 15 years to do a really good job at it, but no. They let me have a shot at it. I don’t know why but I’m really appreciative of that. I think it’s a big part of our culture as you’ve probably heard throughout, what the other ladies have said.

Sandia Ren: Now, as a leader, as a manager, that’s what I try to do as well. I’m so grateful for all the different roles that I’ve had because it’s given me a really good perspective of the business. That’s the type of career path that I want to give to my team as well. My team really focuses on growing people, development. I highly encourage transfers. We transfer a lot of people between consulting and product development, even over to sales consulting and education all over, but I think it’s a win-win for both the company and for our team member. That’s my story.

Roopal Shah: Okay. All right. Hopefully, that gives you some insight into how these ladies got to where they are. I’m going to do a quick hit, just because I want to make sure we have time for these guys to ask questions.

Roopal Shah: We’ll start with you, Eileen. You’re known for your presentations. Do you have any tips, tricks, anything to share?

Eileen Maier: Sure. No pressure. I’m going to tag off with something that Sandia said because she said, “Start with why.” If you’re doing a presentation, you’re thinking about a presentation. First, have an answer to that question: why am I giving this presentation? One of the questions that I’d like to challenge people with is what is going to be different in the universe after somebody sits through your presentation? So why?

Eileen Maier: In articulating that why, you really want to define for yourself where is the audience starting from and then where do I want them to end up? Then, I can get into a lot of techniques of how you tell that story but I think the most important thing is to also remember that it’s not about you presenting it. I’ve got this idea. I want this idea to get across. I know why I’m doing it but I’ve got this audience that I need to pitch it to. You’ve got to spend a lot of time thinking about who is my audience? Why are they coming here? Why are they listening to me? What do they want to get out of the presentation? What do they want to get out of this meeting? How are they hoping that their world is going to be different after they listen to me?

Eileen Maier: I think that that’s where a lot of people fall down because people get so in their head about presentations. They’re in their head because they’re thinking about themselves. They’re like, “I’m going to embarrass myself,” or, “I’m going to put myself out there and people are going to be judging me.” Actually, they want you to succeed. They’re going to be judging you if you get up and you actually waste their time.

Eileen Maier: Spend a lot of time thinking about why you want to give the presentation and then spend a lot more time thinking about your audience because you want to craft your message at a place where they can meet you because good communication isn’t just about speaking good words. It’s about speaking words in a way that they’re going to be heard. That’s really, to me, the key of a great presentation.

Roopal Shah: All right. Thank you. Priscilla, this one’s for you. You’re on the board. I know, for a lot of people, that’s a goal, for whether it’s to get to the highest rung on the ladder or to actually make a big difference. Would love to just get your perspective on what it’s like and just share with us.

Priscilla Hung: Yeah. Interesting. I think that when people say, “I would like to sit on boards as a goal,” I find it very interesting because I will always ask the question, “What do you think board members do that you want to sit on boards?”

Priscilla Hung: First of all, let me show you what board members actually do. Board members have fiduciary duty for shareholders and also as an advisor to the management team but primarily as a CEO and a CFO and key executive of the company. They show up in board meetings four times a year typically and a little bit more, if you are participated in some varying committees, like compensation committees or audit committees, so on and so forth. Of course, you get compensated for that.

Priscilla Hung: When people say they want to sit on boards, you have to understand just like why do you want to be in a certain job? You want to know the job description. It is work and it is work that it will be fulfilling to you, if you want to be in that role, like you want to be an advisor and you truly, genuinely want to help the management team.

Priscilla Hung: Of course, board members are a prestigious job but the thing is, if the goal of being on a board is…it’s a more of a fame or ego-driven goal, then you would not be a good board member and people can smell it because you got to be interviewed to get on a board as well and management team will seek out attributes from you or your vibes, then, “Why do you want to sit on their board,” and how do you help them?

Priscilla Hung: I would say that people typically seek you out as board members as a reflection of all the hard work you put into your career. It’s typically is the experience that you built, the reputation you built that people will come to you and say, “Hey, you have worked in all these company. You have these experiences. We have a company that, at this stage, would like, it would be lovely if you can share your experience and guide the principals along.” That’s you how you sit on a board.

Priscilla Hung: It’s very difficult to set that as a goal because it’s not something you apply for but again is if you focus on your work, you drive, focus, excellent work product and I would say that sitting on boards is a reflection of all the hard work you put into your career.

Roopal Shah: Thank you. It’s working. Thank you for that. Okay. Lerk-Ling, so you’ve been here for 16 years. Can you share with us or what it’s like to work for a mid-sized company versus a startup and any perspectives?

Lerk-Ling Chang: Sure. When I joined Guidewire, there were 12 people. It’s actually the second startup I’ve been at. I was at a previous startup that was not quite that successful. In fact, similar story. It was dot-com bust years, that raised $20 million and then effectively let 75% of the staff go within a year of raising that money. It was those crazy times. I’ve seen the whole gamut of startup all the way through the mid-sized companies.

Lerk-Ling Chang: Some of the things to think about if you’re thinking of do you want to work on a startup? Should you work at a startup? A few things, a couple things. As a startup, you definitely get a breadth of experience across many, many things. In the very early days at Guidewire, I was not only the product manager, I was also the UI designer. I was also the product marketing person, also did the sales demos, also did desk manager sometimes, was also the scrum master sometimes in the QA. The list goes on. Y

Lerk-Ling Chang: ou just do whatever you need to because they’re just not that many people and there’s stuff to get done. The customer is waiting for you. You just do whatever you need to get done. Great experience. A lot of breadth and something you get a lot more responsibility but it’s also very exhausting. You can imagine. Which one do you prioritize? It’s fun whereas as the company gets bigger, your job has to get more focused. It frees you up to actually focus on the things that are most important.

Lerk-Ling Chang: For example, in product management, personally I was very glad not to have to do demos anymore when Eileen joined, for example. I didn’t have to fly to go. It’s too hard to focus if you have so many things to do.

Lerk-Ling Chang: As the company grew larger and you have people who are much, much better at doing demos than I was ever at, I could then focus on being a good product manager. I focus on really understanding what makes the design, what things we should put into the product and how best to do that. That’s one example.

Lerk-Ling Chang: The other example is about, the other thing to think about … Sorry, but this is mid-sized. I talked about the company going downhill, the other startup that I joined. That was, I guess about 20 years ago, but very few people know that actually Guidewire also went through tough times. We actually had a layoff. I can’t remember when that was. You remember that? I don’t remember that. It’s long gone, but very few people know that. Actually, Sandia probably remember that. It was not great. We had to pull the product out from the market, not great.

Lerk-Ling Chang: As a startup, you’re still trying to figure out what the fine line is. You may have gotten one success but to actually get beyond that first few customers, that jump to the next level customers is actually not that easy. Being able to do that successfully is actually a lot of work. It’s a lot of …

Lerk-Ling Chang: I did a lot of things that as a typical product manager in a larger company wouldn’t get to do but it was also incredibly, very stressful. Just those things to think about.

Roopal Shah: Okay. Then, Sandia, I’ve got a question for you. I know one thing that you’re doing is leading this initiative called GROW. Can you tell us a little bit about that and what inspired you to start that?

Sandia Ren: Yeah, sure. GROW stands for a Guidewire Recognizes Our Women. It is an initiative that we have within the professional services consulting team that is focusing on our female colleagues and how to provide better support for them. I think we know the reason for things like this is because we don’t have that many females in the tech industry. Then, you add on IT consulting and then that number really dwindles even more. It’s something that’s been in the back of my mind. Then, certainly, of course, their current events have raised it to the forefront as well, but I have to say it wasn’t really me. Actually, there are a lot of people on the services team, a lot of women on the on the consulting team, that I think we’re sharing the same sentiment.

Sandia Ren: We came together and our focus, again, is I think most importantly to provide a forum so that we can we can understand what challenges women face in consulting and in IT consulting. Then, hopefully figure out things that we can do to make it better. As part of my own research and development, I have gone to a women’s conference earlier this year. I found that just being within that forum and being able to talk to other women like me was a huge help.

Sandia Ren: To be able to hear that one of the most accomplished people in science felt the way that I do, which is a hot mess a lot of the times, was comforting to talk to other women. I see impostor syndrome right in front of me, like it’s yelling at me, but to talk to other women who also feel that way, that, “I’ve no idea of what I’m doing half the time but I’m going to figure it out.” It was really comforting to me.

Sandia Ren: That’s really what we want to do in the beginning is to at least is to provide that forum because I think events like this, it really helps me to be able to talk to other people who are in similar situations and realize that I’m not alone.

Sandia Ren: Those are the things that we want to do with this is to look at women in our consulting team. It’s hard with the travel, especially those who have families and who have kids that we want to be home with and see what we can do to make things better. Then, second, just as important, is to raise awareness.

Sandia Ren: Guidewire has a great culture. We have collegiality as one of our strongest traits but even so, I think there is awareness that can be raised about the challenges that women face. When I’d spoken to my male colleagues about this, they’ve been very receptive. I’m excited to see what we can do with this.

Roopal Shah: Awesome. Final question. Then, I would love to get some questions. Tell us your most embarrassing moment, professionally.

Sandia Ren: I’m glad you qualified that.

Roopal Shah: Who wants to start?

Priscilla Hung: I don’t have any. I can’t think of … Okay. You go. You go.

Eileen Maier: Where do I begin? It’s funny that you ask me the question, Roopal, about presentations because, actually, my most embarrassing moment actually comes from a presentation, so don’t do this. I’m working for PeopleSoft. We’re doing a product launch and we’ve got, I don’t know, five, 600 people at the Hilton up in San Francisco. It’s a big stage and everybody’s in the audience. I’m giving a demo. I’m doing it with my boss. I’m up on stage. I’m up towards the back. If anybody here has ever seen a product demo. Actually in the audience, you really can’t see anything. You have to use big, sweeping motions and so, “Up here, you know, you see blah, blah, blah and if you look down here,” and with one sweep of the arm, I fell right off the back of the stage. I was just gone. I was just gone. I’m all mic’d up. It’s a tuck and roll. I’m under the stage.

Priscilla Hung: Oh, my god!

Eileen Maier: The one thing that did happen that was actually good about this is that it was right before lunch. Now, everybody is now up. They were like, “Uh!” They’re just waiting because … I’ve got the mic on. They just start to hear, “Heh, heh, heh.” I’m giggling under the stage. I’m sure I’m in total shock. I come out from underneath the stage. I pop my head up. I think the really embarrassing part of the story is that, at the time, I had really short, bleached blonde hair. I think that’s really the more embarrassing part but they see this blonde head out on the suit, climb back up on the stage. I don’t even use the stairs. I just climb back up.

Eileen Maier: You don’t know what to do. I’m like, “Well, I guess I’ll just pick up where I left off.” I try to get back into it. I could just tell I wasn’t settled down, the audience wasn’t settled down. If you’ve been on a big stage like that and you’ve just got like these lights in your eyes, you really can’t see anything. I look out into the dark where I know people are. I just look at them. I pause and I say, “I wish I could say that was my most embarrassing moment.” They’re like, “Oh, okay.” I finished out the demo. Then, I think I went back to my hotel room and I crashed for a good eight hours, but I think from that it’s like just keep going. It can try to keep it out of your head and you just get it done. That’s one of mine.

Roopal Shah: Anybody else willing to share?

Lerk-Ling Chang: Mine is somewhat similar. We have an annual user conference. This was probably about 10 years ago. I was doing an intro to new things in PolicyCenter. I’m talking about all the cool stuff that we have been doing the last year, all the accomplishments. Then, talking about one of the biggest news that we had was a new partnership that we had signed that I completely blanked on the name of the partner. Completely, no idea. Silence for two seconds. It felt more like two minutes, right?

Eileen Maier: Mm-hmm (affirmative).

Lerk-Ling Chang speaking at Guidewire Girl Geek Dinner.

Lerk-Ling Chang: Luckily, someone from Guidewire shouted out the name for me, and I just try to go on. Lesson there is, as they say, just go on. We all have that moment. I guess the main thing is you just have to keep practicing and hope that your muscle memory eventually takes over. Mine didn’t, so just keep practicing. Things happen. It’s okay. We all live to tell it.

Eileen Maier: That’s right. You’re still here.

Lerk-Ling Chang: Yes.

Roopal Shah: Anyone else?

Sandia Ren: Mine’s not really funny, so I don’t know if it’s a great way to end, but, so in consulting, you get to meet all sorts of customers with different personalities and different thoughts about the way things should be. Anyway, I was involved, working with a customer. We had gone to do what we call an inception project kickoff. We had done that and then we had finished.

Sandia Ren: Then, what we typically do is we go back periodically to check on how … We do what we call health checks, which is to see how the project is going and check in with the team and check in with the customer and such. I guess either this hadn’t been explained to the big boss in charge or he just didn’t want to spend the money because I traveled there. I showed up. I was sitting there at my desk working away. He comes up to me. He just pretty much hovers over me and says, “What the are you doing here?” I just froze. I didn’t know how to answer that. I stumbled a little bit but eventually was able to say, “I’m doing a health check and these were the benefits of it,” and such.

Sandia Ren: He really didn’t buy into it. That was my last health check at that customer, unfortunately, but I think it was very awkward moment. But, now actually my coworker, who was there with me, he tells everybody as a joke because he thought it was just the most hilarious thing ever.

Sandia Ren: We can laugh about these things years later but I think, at least for me, the lesson learned was that actually I think he was trying to intimidate me. I thankfully recovered and just have confidence in what you’re doing. I got through it.

Priscilla Hung: I really don’t have anything good thing. Maybe just like a little while ago, I forgot what was the fifth thing that my mentor said but now, in hindsight, the whole time of thinking what’s the fifth thing. Now, I recover because there’s actually no fifth thing. It’s the four things.

Roopal Shah speaking at Guidewire Girl Geek Dinner.

Roopal Shah: I would have loved to have things to make. You guys have any questions, concerns?

Eileen Maier: There’s one right here.

Roopal Shah: Mic?

Audience Member: Hi. I can hear you. Yeah. Hi. My name is Vera. I’m early in my professional life. I, too, work at Oracle, first job out of college. I’m currently working in online business sales and I’ve been passively or actively looking to move into another line of business. Sales just hasn’t been for me, but I’m struggling quite a bit. I get calls and emails from recruiters for sales positions but not product marketing or product management or customer success, or other things I’d consider. Do you have any advice from your experiences transferring lines of business?

Eileen Maier: Yes. I think that if you have sales experience and you’ve been out with customers and you have had difficult conversations because selling is not easy. Selling technology is actually very, very hard. You’re facing a very skeptical audience. I think that you have incredible understanding and empathy for what that sales process is like. I

Eileen Maier:  think that there’s a ton of jobs out there in what’s called sales enablement and actually going in and saying, “Okay, I’m going to go inside the company but I’m going to think about the processes of what it takes to actually scale messaging,” because you know what it is that the sales team needs in order to be effective. Big marketing decks that have value propositions that start talking about the company first.

Eileen Maier: That doesn’t actually help you sell. You can come in and you can help organizations understand how do I actually make my sales team more effective? I know that there’s a huge hunger within the industry to actually be able to fulfill that. People typically go into marketing jobs and stuff.

Eileen Maier: I think that, given your experience, that’s a really good transition. I think one of the people that you should talk to, after we get done, is this woman over here because she worked with me but it was really her hard work that instituted sales enablement here at Guidewire. I think that we could probably give you a little bit more insight of some other things you could be thinking about, but that would be something I would think that would be worth you exploring.

Roopal Shah: I think there was another question. Yeah?

Girl geek asking a question to the panel at Guidewire Girl Geek Dinner.

Audience Member: My question is similar. I’m actually in sales enablement and I have a pretty diverse background but I want to scale back into marketing and I’m finding that, because my background is so diverse, it’s hard for me to market myself to a particular skill set. How should I go about doing that?

Eileen Maier: Okay. I feel like Roopal should start to answer some of these questions, too. With sales enablement and you’re thinking about going into product marketing or more corporate marketing or …

Audience Member: Corporate.

Eileen Maier: More corporate marketing. Yeah, I actually think that … I’m going to now reverse it but say the same message, which is I think the most important thing is to have empathy for the audience that you’re trying to communicate to. I think when there’s the corporate marketing mandate and what we’re trying to do in terms of increasing brand awareness and do demand generation or just brand establishment, I think that you’re doing it on behalf of the sellers who are out there in the field.

Eileen Maier: I think using maybe that angle of understanding the audiences that you’re trying to deliver value to, I think is really important because I think often times corporate marketing can get a little bit hung up in the brand and the message and lose sight of the connectivity to the people they’re trying to communicate to.

Eileen Maier: Again, going back to what I said about presentations. There’s always two sides to communication. Think about what advantage you bring, what experience you bring in terms of understanding the dynamics of that conversation because I think that you do have something special, having been on this sales enablement side.

Audience Member: I think that interesting observation during the corporate…

Roopal Shah: It might be working.

Audience Member: It’s impressive staying with the company 10, 15, 16 years, which is rare in the Valley not just from a startup perspective but the fact that you stayed with the company. I stayed at Cisco for 14 years. That does not looked very nicely. There’s a negative connotation. “Oh, you stayed too long. You didn’t change,” but then when I look at my career, I started in engineering, went to business, then went into marketing. I’ve done sales enablement. I’ve been through that journey and I lived globally, which has enriched my experience even further given the opportunities I had.

Audience Member: I’m just curious. Two questions. One is it seems like Guidewire did the right thing, at least from a diversity perspective. Seems like they retain all of you for all these years and encouraged your growth. What was the culture like with the founders?

Audience Member: The second question is how do you address the perception issue, which is completely opposite of what we see right now? Any advice or generally think?

Priscilla Hung: Maybe I can take a stab at that.

Eileen Maier: Sure.

Priscilla Hung: There a couple of things. Your observation is spot-on. I would like to go back to your first question first before we address the culture. Of course, we have a very, very strong culture in the company that we really live by. It’s not just marketing slogan. We really believe in collegiality. We really believed in working amount equals. I think that one of the reason why we stay here so long is I think, I don’t want to speak for all of you, but we genuinely are working among friends. We generally believe in the mission of the company.

Priscilla Hung: Also the company is in the last many years, it’s been doing very well progressively. We’re all proud of being the founding building blocks of it. This company really allow a very basically open view for all of us who developed. We all come into different job and end up here in a complete different job and in high places.

Priscilla Hung: It is an environment, an openness to so focus on not what you look like or what gender it is but it’s purely on how hard you work, are you a good worker, and you got recognized. Also, in my particular situation is, I don’t have a lot of experience in doing a lot of things but it’s so progressively I added more and more to my plates because my boss believed in you a competent person, a lot of the problems are … And, in fact, I think I can generalize it. It’s unlike you’re like a rocket science or you are doing something very specific. I think that going to school, it’s a lot more difficult than working.

Priscilla Hung: In fact, in working, it’s every day is your general competence and general problem-solving can go a long ways, of course, with hard work and dedication. The other thing is really dealing with people. A lot has to do with people, people communication. You work with people. I think that Guidewire paved a very, very good foundation for all of us who thrive and not just us, as all our male colleagues as well.

Priscilla Hung: But go back to the negative connotation as, “Hey. If I apply for another job, you’ve been here for 14 years,” but I think it go both ways. If I’m interviewing for someone right now who want a job at Guidewire and that person has stayed 18 years in a stagnant company, has a poor reputation, bad culture, going nowhere and you look at the progression of the companies, within the company, that person goes nowhere. Then, that is a negative thing but if you are looking at a company that has a reputation like Guidewire or other places that is small and going very big, it’s a is a very attractive profile.

Priscilla Hung: I think you have to put things in context in terms of what you mean by you’ve been a dinosaur in a company for a long time. I think the brand of the company and what it represents makes a difference in terms of the perception.

Sandia Ren: Yeah, and I would add to that, that when we’re recruiting, if I see a lot of short stints, that actually can concern me, maybe just because we’re used to people sticking around so long but it’s certainly something that I will ask is because at Guidewire, we do, we invest a lot in people. We all like each other. We want people to stick around and find their career in growth opportunities within the company.

Audience Member: I realize I’m in the audience but I think … I was at Guidewire for five and a half years, left for three and a half, just recently came back. The reason that I came back was because of the people on this panel and Guidewire cultural integrity. It really is a family environment.

Roopal Shah: Here, here.

Audience Member: Okay. I have a question.

Priscilla Hung: Oh. You’re…

Roopal Shah: Lisa Walsh, our Vice President of Alliances. There you go.

Audience Member: And anyway. You guys all talked about the importance of relationships and people in your careers. What do you look for, someone that you choose to mentor? Sort of like start to pay back. What are the attributes of someone that you think could be a good mentor, that you would like to mentor?

Sandia Ren: I can take that. Actually, as I mentioned, I was just in K.L. We were looking for a manager for the office and we were interviewing, met a number of a number of candidates who had managing teams for 10, 15 years, built teams from scratch, et cetera but then we met this girl or, I should say, woman. This woman who was … She even called herself a new leader. She’s only been managing team for a two and a half years but, as I talked to her, I could just tell that she was really smart, really clued in.

Sandia Ren: She really quickly picked up on the things that we were talking about. She was really excited to learn. She says she wants to switch jobs because she wants to be exposed to more people, different people because she thinks that that’s how she’s going to learn. I could tell the ambition was there and just the openness to learning.

Sandia Ren: Now, I’m like, “How do I hire her,” even though she may not be the best fit for what we’re looking for but it’s that eagerness to learn, that passion, I think that goes such a long way.

Lerk-Ling Chang: Yeah.

Priscilla Hung: I mean, for me, it’s just to build on that a little bit. I think, for me, it’s the chemistry has to work because I really believe in mentorship because I owe my career to my mentor, but first of all is you can’t mentor 200 … I mean, it’s the time with issue. I think that when you click, you click. Also, the second thing is just like Sandia said is, you will get a sense that whether the person in front of you actually is open due to change. If there is closeness there, it’s a waste of time.

Eileen Maier: Thank you, because we’ve been talking about this, Lisa. I think one of the things that’s really important is people say, “Well, you know, I’d like to find a mentor,” and, “It’s so important to find a mentor,” but I think this is probably the most important thing you need to know is that you actually get chosen. You can ask somebody to be your mentor but you are going to get chosen. It’s really how do you represent yourself as somebody who’s open?

Eileen Maier: You’re whip smart. Show that you’re whip smart but recognize that that’s how the relationship is going to happen is that you’re going to get chosen by that person because I think that if we think about people that we’ve mentored, it’s because that connection happened.

Eileen Maier: Make yourself available to those people that you’d like to mentor you and see if you can establish that connection in somebody’s … I guess I’m also saying you have to earn it.

Roopal Shah: I think we have time for … Okay. We’ll take these two as the last two. Do you need a mic?

Audience Member: Thank you. I’m really happy to have heard stories from all of you because just today I was feeling a little bit … “I’ve been at my company for 13 years. Am I considered a dinosaur?” Now, I don’t feel so bad because, like you said, I’ve done four different roles at the company. I know I’ve grown with the company. Thank you.

Audience Member: As a new manager, we were doing more focused on execution and planning. As I grew into a director role, it’s more about strategy. What is it at the VP level and at the COO level?

Priscilla Hung: That’s a very loaded question. I would say that, as a COO … I was just joking. Who I was talking to? My memory’s going. I was talking with someone today that I’m actually not really doing much. I’m not saying I’m lazy, but on a day-to-day basis, so my job is I’m thinking all the time. My job is to think about are we heading in the right direction? If we’re not headed in the right direction, how do I direct or influence the team to go to that direction? How do I make sure that people actually work together?

Priscilla Hung: That’s my job but I’m not giving you code. I’m not writing a paper. Sometimes I’m not doing my PowerPoint. Higher you go, it’s more about overseeing people. I would just say that when you’re individual contributor, you are measured on and you probably have something tangible that you’re delivering but as you get higher and higher, that becomes probably not majority of your job.

Priscilla Hung: Most of the time is you’re really thinking you’re working with people, you’re managing people. You’re making sure that you drive productivity in your team. I would just say that you think more and you work less. You produce less from the perspective when you get into more senior position.

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