“Office Manager to CPO – Keynote”: Shawna Wolverton with Zendesk (Video + Transcript)

June 21, 2019

Shawna Wolverton is a self-proclaimed nerd for good product design. Starting at Salesforce in 2003, Shawna worked her way up to SVP Product Management, influencing $30M/yr in revenue before she left to do it all over again as CPO at Planet and now SVP Product Management at Zendesk. Don’t miss this session as Shawna shares the lessons she learned both personally and professionally in her 25 year career.


Shawna Wolverton / SVP, Product Management / Zendesk
Sukrutha Bhadouria / CTO & Co-Founder / Girl Geek X


Sukrutha Bhadouria: Hey, Shawna.

Shawna Wolverton: Hello.

Sukrutha Bhadouria: All right, so gentle reminder of a few things, so I’m Sukrutha. I’m CTO of Girl Geek X. We’re recording these videos. They’ll be available for you in a week. Post your viewing party, selfies of you watching this, and any other learnings that you have on social media with the hashtag GGXElevate. We’re going to do a Q and A at the end, if we have the time. So, use the Q and A button at the bottom to ask questions. If we don’t have time, we’ll answer the questions later tomorrow or later this week. So, please check out our job board on GirlGeek.io/opportunities. Yeah, that’s it.

Sukrutha Bhadouria: So, let’s enjoy Shawna’s talk. Shawna, Senior Vice President of Product Management at Zendesk. Before which she was the chief product officer at Planet. Prior to that, she spent 14 years at Salesforce, going from the first localization manager to growing into being the Senior Vice President of Platform Product. So, that was a great growth, and Shawna is going to be talking to us today about her growth from office manager to CPO in over a thousand steps. Thank you, Shawna, for making time for us. I’m super excited.

Shawna Wolverton: Thank you. Awesome. I will just jump in, since we’re running a little late on time.

Shawna Wolverton: Welcome, everyone. I hope you’re having a great day here. Thank you so much to the Girl Geek X crew for hosting today. I’m really honored to be here. And, as Sukrutha mentioned, I have had quite a career, not always the one I planned. It’s been an interesting odyssey, and I thought I would share a little of that with you.

Shawna Wolverton: And really, this is the only good place to start, because so much of my career really does come down to this. I think there is some myth out here that we can all– we’re self-made, we’ve worked hard, every accomplishment we have came–just sprung forth from our amazing intellect and crazy persistence. And I don’t want to discount that, but the universe is large and we are all very, very lucky to have been born in this place and time. And so many people have helped me along the way, and I’m incredibly grateful to them.

Shawna Wolverton: But really, when I think about career plans, we just heard a little from the good crew of Grand Rounds about planning. And so much of life is really a fantastic stochastic kind of adventure. And we can’t always get all of the steps right for how we want to get there. But, at the end, there’s some really great goals and great milestones that we get there.

Shawna Wolverton: So, in my lifetime, we had an entire industry come and go. We had entire things– dotcom dissolution, number one. We had a grand financial crisis. Entire industries are gone. So, we really have to think about agility. We do it a lot, in terms of how we do our work. But I think we sometimes kind of get a little locked in and forget that we wouldn’t make a solid waterfall five year plan to do anything else in our lives. And being agile in our careers is really critical.

Shawna Wolverton: And there’s no one right way to go, and sometimes things change. I spent the first 20 years of my life assuming I was going to be a physician. It turns out my university transcript and I had very, very different ideas about that future. And there was no product management Barbie set when I was a kid. And coming out of school with my fantastic degree in Russian studies and political science didn’t set me up for anything really obvious. And it took quite a bit of experimentation and curiosity. And I think that early curiosity is what has also kind of driven a whole bunch of my career. A strong desire to learn new things, and an absolute hatred of being bored has been probably the two biggest things that have driven my career to date.

Shawna Wolverton: And I think we think a lot about driving our careers. We hear about this all the time, right? What are you doing to drive your career? What are the activities that you’re doing? I think we get a little lost sometimes and lose the journey. I like car racing, maybe you don’t, but I thought this was a really amazing analogy, right? There is a fantastic race that goes from Paris to Dakar in Africa, and you have this amazing adventure. And you have a whole crew that comes with you, because you assume your car will break down, and you will go the wrong way, and it will take much longer than you anticipated. And it’s glorious. And the sort of alternative is this ring of never ending struggle.

Shawna Wolverton: And I think, when you think about your career and how you progress through it, kind of an adventure attitude and a fantastic kind of see what will happen is a great way to approach things and make sure that you’re not missing out on the amazing experiences that come sort of between those promotions. I think we sometimes put milestones in the ground about where we’re supposed to be at certain points in our lives. And, when we don’t get there, we can be really disappointed. And I always think that’s really unfortunate, because there is so much to learn along the way on these journeys.

Shawna Wolverton: My career was clearly not a straight line. I did start out as a localization project manager. You can see I did that job three times in my career. Sort of moving on from it, finding myself in a position where it was skills I needed to rely on to kind of go back into the job market when things had changed. I certainly didn’t expect to learn much that would help me in my career, taking that nine month apprenticeship as a handbag manufacturer with an Hermes trained designer. But, my goodness, did I learn a tremendous amount about human nature, about satisfying the wants and needs of customers in a way that I don’t think any other technology job would have given me.

Shawna Wolverton: And it was a tremendously long time between that first localization manager job and that SVP of Product manager job. I spent 14 years in the same job–or not in the same job, but with the same company, at Salesforce. And I think it’s another thing we think a lot about is, have I stayed too long? Have I stayed long enough? And I think that a lot of those thoughts are silly. If, like the previous speakers were saying, if you find the thing that matters and that gives meaning for you, then you keep going, and that’s what gets you up in the morning.

Shawna Wolverton: I like to tell people that product management is a job that by all measures is pretty terrible, right? If everything has gone swimmingly well, you’ve reflected that back out on your developers, your sales engineers, your sales team, your marketing team. And, if it goes absolutely sideways and the organization is at a loss, you stand up in front of the room and it’s all you. But what I found is that there was this fire in my gut that was about helping customers help their customers. And I couldn’t imagine doing anything else. And I think that love of my customers and that sort of obsession with helping them is the other sort of huge part that grew my success.

Shawna Wolverton: And then, I think this is a big thing that we don’t talk a lot about and that’s the–well, we do. We talk about it a lot. Who am I kidding? But having it all is a lot, right? You can have a family, and children, and a job and it’s not easy. But I think a lot of the things that we tell ourselves and a lot of the things that the media tells us about what it’s like to be a working mother are really bananas. There is this myth that we’re going to go out on maternity leave and we’re going to come back and we’re going to be distracted and we won’t be as good as we were. And there is this amazingly strong body of scientific research that’s happening about what happens when, not just women, but men and women come back from parental leave or after the birth of their children.

Shawna Wolverton: Amy Henderson, who is the founder of a company called Tendlab that really focuses a lot on sort of parenting in the workplace, has done this amazing research. And the women primarily that she spoke with, the senior women, all with hindsight, were able to look back and find an acceleration in their careers post childbearing. And I think, whether you have children or not is a totally personal choice. But I want everyone to know that it’s not, I think, the horrible, awful, career ending thing that we’ve thought it was for the longest time. And there is a fantastic thing that can happen. That little J curve was definitively, after my daughter was born. And, at 12, we’re having a fantastic time together in a way that allows me to be here and also there, and to be a fantastic role model for her about what it looks like to be a woman who is in the workforce.

Shawna Wolverton: And this one is important to me. It’s, success is not a pie, right? I think oftentimes we think for us to win or to get a promotion or to get ahead, someone else has to lose. And it’s not like there is this finite amount of success where we get our pieces of the pie, and we eat it, and then they’re all gone, right? It is really more of this sort of random, infiniteness that is more pi than pie. And so much of I got to where I am is about the people who put a hand out to me and who supported me in my career.

Shawna Wolverton: You heard from Leyla and Jen earlier. A huge part of my network of support in my career. And it’s incredibly important, I think, for us to think about how we turn around and put our hands up too for the next group of women coming up in the world.

Shawna Wolverton: So, yeah. That’s sort of my journey through my career. I think I went a little fast. I woke up this morning with a cold and I’m on a little cold medicine. So, maybe I’m going a little fast today, but it might leave us with a little more time for Q and A.

Sukrutha Bhadouria: All right. Shawna, that was amazing. My video feed is taking a bit of time. Hi.

Shawna Wolverton: Hi.

Sukrutha Bhadouria: You’re so awesome. I love the fact that you said that success does need to be shared, for sure. Sometimes we’re a little bit hard on each other, right? And we get a little competitive and we don’t help each other out enough. What has been, I guess, for you–I have a question. What has been, for you, the most fun role that you had while you transitioned over the years?

Shawna Wolverton: I think almost every job I’ve had I’ve found the fun. But I think I have a kind of warped sense of fun. Things that are really, really hard are fun. So, at Salesforce, we had a giant project to rewrite the entire front end of a 17-year-old software product. And it was an entire company motion, took me way out of my comfort zone, and it was hard. But, at the end, it was just so fantastically rewarding. And the fun part was really so much about the people and conscripting a sort of unwilling team onto team lightning, and then going out in the world and talking to customers about it.

Sukrutha Bhadouria: Yeah.

Sukrutha Bhadouria: There’s another question. What is a mistake you made in your journey that you could share with us?

Shawna Wolverton: I think one of the mistakes I made was thinking that I could go fast. Like there were times in my career I got a little ahead of my skis. Where I saw other people getting promoted, I let my ego get in the way, and, when I didn’t get a promotion I asked for, I took it really personally. I was devastated. And, in hindsight, I’ve realized that extra year spent in the job before I promoted was important, and I learned a lot. And I wasn’t ready when those things had happened. So, I think–yeah. Getting a little too attached to my own ego and letting some of that go.

Sukrutha Bhadouria: Yeah. It happens to all of us, I bet.

Sukrutha Bhadouria: Okay. We have another question that says, how did you get the opportunity to be a handbag apprentice for Hermes? How does one find additional opportunities like that, Shawna?

Shawna Wolverton: Strange things happen when you take City College classes for fun, and you meet interesting people, and when you’ve been laid off, and you have a little bit of severance, you can say yes to some things that you normally wouldn’t say yes to. I think I probably would have stayed longer, but my husband started sort of like, you know, it might be time, Shawna, this little adventure you’re on.

Sukrutha Bhadouria: So, what do you think kept you going when things were not going the way you meant for them to go? Like how do you keep yourself positive?

Shawna Wolverton: I mean, I think, for me, it’s about what’s always been important to me. And what I found when I became a product manager, and why I’ve never wanted to do any other jobs since I started is that connection to customers. And knowing that, even when things are really hard or things aren’t going great in the office, that the things that I do have impact on real human beings. And I was lucky enough, over the course of my career, to really get to know–I count a number of former customers as friends today. And getting to know how the things I did impacted their lives, and that really is the thing that keeps me going.

Sukrutha Bhadouria: All right.

Sukrutha Bhadouria: So, some more questions pouring in while I’m reading them out. So, what is the biggest leap mentally and leadership wise you think you experienced in moving from director, to VP, to SVP, to C-level?

Shawna Wolverton: Yeah. I mean, I think one of the craziest things is about–I mean, it’s funny, I talk about this a lot–and I noticed it the most when I became SVP, and that’s moving from what I call the person who was sort of, I had this brand as being the person who fought the man, right? I was speaking up for the customer, and I was really adamant, and I was pounding the table, and sort of advocating really hard, often against management. And then, I became the man. And it was a really interesting adjustment for me to understand that, often, there is a toll in this sort of, I disagree but I’m going to commit and go forward that is really required at an executive level. And that adjustment was probably the most interesting of my career.

Sukrutha Bhadouria: Wow. All right.

Sukrutha Bhadouria: Maybe last few questions. I’m curious because a little birdie told me you were best known for getting the customers to fall in love with you. What’s your secret?

Shawna Wolverton: Oh, listening. I think a lot of it was really active listening. And then, here’s the strange thing. I told them no. And I think sometimes we try to please customers, or bosses, or colleagues, and we say, oh yes, all the time. And then, we either can’t deliver, or can’t deliver in a timeline, or people make plans based on that yes. And sometimes a really, really clear, I’m not going to be able to do that is so much more powerful than our sometimes, like, extreme anxiety about wanting to be able to say yes.

Sukrutha Bhadouria: That’s amazing. I didn’t think of that at all.

Sukrutha Bhadouria: Just one last question, and then we should wrap. What was the pivotal moment that helped propel you into senior management roles?

Shawna Wolverton: Yeah. I mean, I think a lot of what I did to get propelled into senior management was taking on projects that no one else wanted to do. I’ve had the good fortune, I don’t know, to work in really fast growing companies where there was always more work on the ground than there were people to do it. And finding out which one of those things was actually really important, and then taking ownership of it, and showing management that I was the kind of person who could take on those hard things was a huge part of my career growth.

Sukrutha Bhadouria: Thank you, Shawna. This brings us to the end of your talk. Thank you everyone who posted questions and the amazing comments. By the way, you got a lot of love for your glasses.

Shawna Wolverton: Thanks.

Sukrutha Bhadouria: Thank you again.

Shawna Wolverton: Thanks, everyone. Have a good rest of your day.

Sukrutha Bhadouria: Thank you too. Bye.

Shawna Wolverton: Bye.

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