Stevie Case (Chief Revenue Officer at Vanta) believes that the perfect resume is a myth, high level tech sales roles can be done by almost anyone, and that these roles should be the #1 pathway into tech. She shares her own career path (including being the first professional female gamer) and encourages women to embrace discomfort to grow.
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Angie Chang: I’m so excited that we are here today. If you can cheer us on in the chat, we really appreciate it, and tell us where you’re coming in from. I see we have people from all over. We have over 2,500 people signed up so far, and we’ll be open all day for registration, so if people are interested in joining, they can totally do so at any time and just register and click on that join link.
Sukrutha Bhadouria: Yeah. Hi, everyone. Welcome to ELEVATE 2023. Loving seeing everybody telling us where they’re joining in from. This is our sixth annual Girl Geek X: ELEVATE virtual conference where every year we celebrate International Women’s Day. This is Angie who just spoke and she founded Girl Geek X. It was originally called Bay Area Girl Geek Dinners, started all the way in 2008. Some years later, I’m Sukrutha, I cornered Angie into joining her and together we saw, with a lot of help around us, we saw this really take off from small meetups to huge, huge in-person meetups every single week. Booked up all the way to the following year. And then we were commuting to an event in the South Bay. Angie and I started to talk about what else could happen with this, and we are like, “Let’s do conferences and let’s keep it virtual, so we go beyond the Bay Area.” And that’s where we ended up. We also did podcasts along the way, and what we struggled with in the pandemic is while virtual, how do we also still encourage people to network? Which is why we incorporated the networking aspect into this particular conference. You must know somebody from everybody around you who’s looking for a job, especially in this climate. So, please do look at our sponsors page. The girlgeek.io/jobs link will take you to our list of sponsored jobs. Angie, do you want to give a shout-out to our sponsors?
Angie Chang: Yeah, we’re really excited to have Autodesk, Cadence, United States Digital Service, Dematic and CodeSee with us as sponsors and government participants, and you’ll be hearing from some of their women leaders and founders later today and tomorrow. I really encourage you to check out the agenda and go find them and bookmark them, so that you don’t miss a thing. I know it’s a really hectic day, so if you bookmark the sessions, you’ll get a calendar invite so you won’t miss it. And the link is girlgeek.io/jobs.
Sukrutha Bhadouria: Yeah, today we’ll be hearing from a diverse set of women working in various roles in tech, right? And that’s what we really are passionate about, Angie and I, we want to give the mic to anyone who hesitates to share their story, share their journey, and hence, end up inspiring more and more people to not just get into but stay into tech. In many years that we’ve been doing this, we’ve dramatically seen a shift in people wanting to get more, do more, push themselves more, and as we continue to see ourselves move the goalpost for ourselves, we also need to take a pause and take care of ourselves. So, throughout this sessions today and tomorrow, you’ll see us balancing that conversation. How do you seek out more while also putting yourself first? So, it’s going to be amazing and very, very interesting. But Angie, since we have you for a few minutes, we should hear from you, what’s the flavor of the week? What’s on your mind right now?
Angie Chang: I’ve been thinking about all this talk about imposter syndrome, and I also want to turn it back and say there has to be systemic change in the way that women are promoted throughout the levels. And I encourage women to come to events like the Girl Geek events and get out of their own organization or their own small group. I used to be in engineering and then I was in product and I was in these very small groups, but I also think that we need to look at how teams can work together to figure out how to solve these structural problems that exist across companies and not just your company’s problems, because they exist all over. And so together, we can work together in these big structural problems, hopefully, or point to researchers and Harvard Business Review researched on how to solve for that and not just say we all have imposter syndrome, which we do, but let’s leave that over there along with the bad stories you tell at the bar, and go ahead to find solutions together. I think that is what I am thinking this week.
Sukrutha Bhadouria: Well, I’ve been thinking about it is a very, very difficult place to work, this industry in the first place, and then now this industry is going through so much of a struggle with all the layoffs and I see so many stories that people share on LinkedIn about how much they’re struggling. And I keep getting reminded of, how do you lead people through these difficult times and how do you lead yourself to navigate through these difficult times? And something that keeps coming back to me is this piece of advice a mentor gave me several years ago, that it’s more important to lead with empathy than with force. So, whether you are navigating your own career or you’re trying to motivate your team through a difficult time, put your heart first, because that’s what’s going to last the longest. Yeah. Well, and with that, I want to remind everybody we have hashtags to use, so please continue to share the love on social media with the #ElevateWomen, because we want you all to lift as you climb, and the #IWD2023, because it’s International Women’s Day and we are so excited to have you all here with us today. Anything else, Angie, before I welcome an amazing, amazing speaker, Stevie?
Angie Chang: No.
Sukrutha Bhadouria: All right. We have our keynote speaker, Stevie Case. She’s a Chief Revenue Officer at Vanta. Before that, she was VP at Twilio, and also is an angel investor and advisor. Welcome, take it away.
Stevie Case: Thank you so much for having me. Good morning. I want to share a little bit of my story this morning because the truth is, I was never qualified for most of the jobs that I succeeded in. I want to start with a story of this girl, this young girl in the late 1970s, growing up in Kansas, not exactly a tech hub. Growing up on 300 acres of prairie, I actually did grow up in a little farmhouse on the prairie. And I grew up with a mom and dad who were very idealistic, who were not at all connected, who had big ideas about helping people. My dad, a biologist, my mom was a nurse and later, a social worker. They had really incredible view of the world, but we also had a pretty limited view of the world.
Stevie Case: Growing up in the country in Kansas. Growing up poor. I certainly had no passport. I had no concept of what was beyond the state borders in many cases. I definitely knew nothing of tech, but I did have big dreams. And as I made my way through high school and I saw what was ahead, I dreamt of being a lawyer, being a constitutional lawyer of all things. This is a real picture, I actually met Bill Clinton at the White House. I was on this path. I felt like, “Okay, I’m on my way. I’m going to go to law school and map out this future helping people.” At that point, I believed that politics was a great path to helping people. I’ve got mixed feelings on that now, although a lot of people are doing incredible work out there.
Stevie Case: And that idealism carried me through to college and I went to the University of Kansas, right down the street from where I grew up. Still big dreams of going to law school. And then this happened. If you were around in the late ’90s, early 2000s, you might recognize this as a LAN party. You’ll see the 21-inch CRT monitors back in the day. That person in the red circle there is me. And you’ll note, I think I’m one of two women in the room in this photo. And this was the beginning of the great derailment of my plants.
Stevie Case: And this moment came about because I started playing games. At the time we were playing Doom and then Quake. We were playing games in the dorm and I lived in this dorm on this honors floor, with all these really smart guys. They introduced me to these games and I fell in love with playing these games and I got quite good at it. And that took me on the road. I got to meet all these gaming legends. I got to play a variety of games and I got to compete. And as I competed and got better and better, I got the opportunity to challenge the man who had made one of those games. I ended up beating him at that game and I ended up dropping out of college.
Stevie Case: Imagine being my mom at 10:00 PM on a weeknight, when your daughter shows up with the U-Haul and says, “I’m moving to Dallas, I’m dropping out of college, I have no real plan and I’m going to just go down there and play video games.” This was not a popular decision in my household, but it did lead to this and it mled to some really interesting adventures. I got the opportunity to play professionally, to travel all over the world, and then ultimately, to make video games. I saw this evolution that I could undertake to get deeper into the industry.
Stevie Case: I took every opportunity to learn and ended up making video games for a living, and that was my detour into tech. Flash forward 25 years, it wasn’t all rosy, as you can imagine, in an industry that at the time was like 98, 99% male. It was rough. I was almost always the only woman in the room. I endured a tremendous amount of harassment and sexism and things that today blow my mind that they actually happened in the real world. And I recently told that story just last year in Vanity Fair.
Stevie Case: I’ve had an incredible adventure since then. I’m a single mom. This is my daughter. She’s 18 now. That’s her senior picture on the right. She’s a total sweetheart. She’s just about to graduate. I’ve had full custody of her since she was three. That was also not the plan, but here we are. And now, I’m the chief revenue officer at a company called Vanta. This is my team, just a few weeks ago, kicking off our year down in Austin where we did a big revenue kickoff event. Vanta is a unicorn. It’s a more than billion-dollar company and it is my first role in the C-suite at a company of this size. And we work in security and compliance, which is again, a fairly male-dominated industry vertical.
Stevie Case: I am so grateful for this ride and I could not have predicted it if you look back 25 years. Even at the beginning of my gaming career, I had no idea this is where it would take me. Over 25 years, I’ve built an incredible career. I am a self-made multimillionaire. I’ve got this daughter about to graduate high school, and I’ve got a life I am so excited about. But when I look back at the reality of everything I went through, I was absolutely never qualified for the vast majority of roles that I ended up taking and succeeding at.
Stevie Case: I’ve joked about this in some of the roles I’ve taken over time, that if you actually looked at the job description for the job I was doing, if we had a job description on the website, I didn’t meet the criteria. I was a college dropout. I didn’t have all the check-boxes. And yet, in each of those roles, I found a path to success. And I’m here to tell you today that there’s nothing magical about what I did, and I don’t think there’s anything particularly special about how I plotted my way through that journey. There are a bunch of tactics that I used, that I believe anyone can use to help open up opportunity and to plot out the kind of unique career with a unique background that I have been so lucky to have.
Stevie Case: I want to make a special pitch too, for tech sales. Sales has been really good to me and I think there are great reasons to consider it. I know that in tech there are times when it’s frowned upon, it’s seen as less technical or less sexy than coding, but I’m here to tell you it’s actually a great career.
Stevie Case: Let’s flashback a little bit to the beginning of that journey in gaming. I want to tell you a little bit more the mechanics of how I made my way to where I am now and then some of the tactics I used along the way. Flashback to the early 2000s, I was a pro gamer. I knew I wanted to make games. I knew that gaming itself had a shelf life. You’ve got have great twitch reflexes and I thought, “Okay, I want to become a designer. That seems like a great path forward.”
Stevie Case: I thought, “I need to gain some technical skills of some kind.” And the only technical job I could get at that time was taking calls in a call center. It was a support call center for Toshiba laptops. I will never forget this experience, and it was very much a fake-it-until-you-make-it experience. I had to learn along the way. I had to study and I got actually quite good at tech support. I continued to work within the gaming scene. I got an offer to do quality assurance work at a video game company. And this, to me, was a huge win. I got to join the team onsite, go work in the big office with the creative team. And granted, I was the lowest paid person at the entire company, paid less than our receptionist. It was total hustle, and I was so thrilled. And I took that job and again, I learned, and I would find time to go talk to the designers. I was trying to absorb everything around me. At one point, I slept at the office for two weeks and kept a suitcase under my desk, trying to learn the business.
Stevie Case: Over time with enough hustle, I got the opportunity to get a design job and I worked on the product side of games. I continued there in Dallas doing that for several years, and after a relationship gone bad, I fled to LA, and in LA I found more opportunity in gaming and I ended up at what I felt at that time was the pinnacle, as good as it gets, I was at Warner Brothers making mobile games and it felt like, “Oh my gosh, I’ve made it. I can go on this studio lot.” And for a Kansas girl, there are actors and celebrities and I’m making content with all this great IP. “This is it. I have made it.”
Stevie Case: And along that journey, I had a vendor and he approached me and said, “Hey, I need a junior salesperson and I think I can teach you to sell.” And I had no idea what that meant. I had a huge amount of social anxiety, I was very shy, and it sounded honestly, deeply, deeply uncomfortable to me. But one of the things that has defined all the life-changing moves I’ve made in my life is that they felt deeply, deeply uncomfortable and scary. So, I thought, “If I’m this scared of this, I probably should do it.” And I did.
Stevie Case: And ever since, 15-plus years on, I have been in sales. And through that journey I took first just a job as a junior salesperson. I went on the road. I was really bad at it. I had a great mentor who really just beat into my head what great sales looked like, what it looked like to be vulnerable. One of those core lessons he taught me in those early days is that the best way to have success in sales is to just be authentic and be vulnerable, and it’s actually okay if you make mistakes, because that gives the other person permission to be human. That lesson really stuck with me throughout my career.
Stevie Case: I started to climb the ladder. I had some great leadership roles. I started to have the opportunity to run a team. I ended up as a VP at a company that was acquired by Visa, worked my way into additional opportunities, running everything revenue-facing. And ultimately, I landed at Twilio, and Twilio was an inflection point in my career. When I was offered the opportunity to join, they offered me either an account executive, a salesperson role, or a leadership role, and I decided I wanted to have the opportunity to just own the quota.
Stevie Case: Twilio was very early, it was all self-service. There was not really a sales team, and it felt like kind of the Wild West. I thought, “If I can just be an enterprise salesperson and go sign a bunch of big deals, that could be a really cool experience.” So, I did that. Ended up spending six years at Twilio, first as an enterprise AE, signing deals with Fortune 500 companies for them, then as a frontline manager running a team, then as the second line manager running the Western US, and ultimately, as the leader of the mid-market business, a $400 million business. And at each step, there was so much luck involved and so much pressing forward and learning and challenge and deep discomfort. But there are some tactics I used both inside Twilio and along the way to get there, that I think everyone can leverage. I want to share those with you now.
Stevie Case: If you want to build an incredible career with a non-traditional background, my tip number one is that the online application pretty much will never cut it. When you’ve got a unique background, what makes you so special and a compelling candidate to any hiring manager is really difficult to articulate in a resume. And as somebody who is currently a hiring manager, I can tell you the deluge of resumes is incredibly hard to break through. If you are unique, if you bring a special skillset, it’s incredibly important that you get in front of people with your story, and your story in particular about what does make you unique and why someone should take a chance on you.
Stevie Case: Don’t settle for the online application. And if you get a lot of rejections through the online application, do not take it personally. It is not about you. There is so much limitation in a single page of paper that misses everything that matters about who you are. So, never settle for the online application. It’s got to be about the human connection.
Stevie Case: Number two is, own your story. And what I mean by this is, be you. You don’t have to fit the mold of what people are expecting. And rather than coming into a role, if you’re going for a stretch role, if you are applying for a job where you know you don’t meet the criteria, own that. Don’t pretend that you fit in that box, because if you pretend you fit in the box, you’ll often then get put up against the standard criteria. Hiring managers will say, “Uh, I’ve got somebody that fits this set of boxes better.” And it will be a struggle to succeed.
Stevie Case: What you’ll find is that if you truly own your own narrative and especially the parts of it that are unique about you, that will resonate, because really, hiring managers are looking for somebody that can do the job and can do so uniquely. And job descriptions are a very inaccurate and very rudimentary way to describe what they need. It’s a vague notion of what’s needed to succeed in a job. If you own your story and you tell them why you’re uniquely suited to do the job for reasons that aren’t on the page, that’s often much, much more compelling. And owning your story can mean writing it down. Get down the elements of your narrative that you think are unique and memorable. And be vulnerable. It’s okay if it’s not perfect and it’s okay if it doesn’t meet the requirements.
Stevie Case: The next is, do great discovery. And discovery is a word we love in sales. It really just boils down to asking great questions. Doing great discovery means figuring out all of the details about the situation, the people involved, what the expectations might be. And in many cases, especially if you’re looking to make a career pivot or you’re reaching for a job that you might not meet the requirements for, sometimes it’s just about knowing the right words. It’s incredible the power of mirroring and of spending the time to understand how the hiring manager and how the team you’re trying to join thinks about and talks about their business.
Stevie Case: Now, as you do this, one thing that I think is really important is that a lot of people who are trying to break into an industry or get a new job, they shoot high, they’ll go to the most senior person in the org or the hiring manager, or their boss. I would actually encourage you to make that connection and do discovery with people who are in the job today, people who are perhaps a little bit lower in the org chart, who are going to have more concrete information about the expectations that might help you form a great story about why you would be so wonderful for this role.
Stevie Case: Meet people, ask little of them, and just absorb their knowledge. You can do this in adjacent industries and folks who are in that role today, but ask the questions and spend the time to get to know people. You’ll be shocked in the ways that it pays off.
Stevie Case: The next is to paint the art of the possible. One of the things that really strikes me about hiring is that folks who are coming in who might be intimidated by the role they’re applying for, they want to justify their background. They’ll tell you a lot about the past, but really what hiring managers care about and what people building businesses care about is the future. One way you can counteract having a less-than-perfect resume or a non-traditional story, or different background than they might be looking for, is to talk to the hiring manager and talk to folks in building the company about the future and how you can help them build that incredible future.
Stevie Case: One way I manifested that at Twilio, when I was up for the VP role running this $400 million business, I had never run a $400 million business before. What I tried to focus on was rather than giving them proof points that might show them in the past, I’d done something similar. I focused instead on telling our CRO about my vision for the future of that business and how I was going to take it from $400 million to a billion dollars, and that forward-looking vision was compelling, and I explained the how. That got him on board, that while I might not have done it before, I did have a vision for it and I understood how to make it happen, and he was willing to take the risk.
Stevie Case: My next tip is, seek out opportunities that lack definition. If you’re trying to make big leaps in your career, if you’re trying to do something new, you’re going to have more luck doing that in places where it’s either early stage, people are building things that don’t exist before, or there’s a new opportunity that isn’t yet well-known. So, seek out these areas where it’s sort of the Wild West and you can help define and build something from scratch. It’ll give you an opportunity to show your unique skills and really stand out from the crowd, because you know that what you’ve got in your background makes you unique. Use that uniqueness to build something great where the expectations aren’t well-defined. In these situations, you’ve got a real chance to succeed and exceed expectations.
Stevie Case: And along the way, remember that every hiring manager is just another human. Everybody you’re trying to do business with, get a job from, connect with, they’re just other human beings. I have met some of the richest and most powerful people in the world. They’re not special, they’re just like you, they’re just like me. They’re just people. Approach them from the point of view of an equal. Approach them with confidence and vulnerability. Treat them like a human being and not somebody magical, special. Just be kind, just be normal and you’ll be shocked how far it goes. It’s very rare actually, the more senior you become that you get that equal treatment, and it’ll go a long way in establishing you as an equal on the playing field.
Stevie Case: And developing champions. I cannot recommend this enough. One of the ways that I see this go wrong is I think early in career, especially folks who are coming from backgrounds outside of tech, feel like they have to have formal mentorship. And formal mentorship is great, but what I have found in my career is that most of the folks who can actually make stuff happen for me, don’t have time for formal mentorship, but they’re willing to make things happen for me if they believe in me and if I’m willing to ask them and try to learn from them and also be respectful of their time.
Stevie Case: These are three of my champions. Matt Golden, on the left, was the first person who gave me a sales job and believed in me and taught me and was very hard on me and made me so much better. Alyson Welch, at Twilio, promoted me into a second line role when I’d never been a second line leader before. George was my COO at Twilio. He taught me so much and would really just open my eyes to the possibilities. I would not be in the C-suite today if it were not for George.
Stevie Case: Find your champions and be careful with their time. Don’t demand too much of their time, but really try to get deep on how they think about it, because the truth is as you move up, every role is a different job. The job of a salesperson and a frontline manager are extremely different. The goals are different. The way you think about the business is different. And every time you want to make that move up, start trying to discover from these champions how they think about that role and what matters there.
Stevie Case: And my favorite probably, celebrate discomfort. My most successful moves have come when I was deeply uncomfortable and I would encourage you to lean into that. It is okay. The worst case scenario is probably some embarrassment and an overreach of what is possible. And that’s okay. The world won’t end. And the more you lean into that discomfort and the more that you take those risks, the more you’ll know you’re growing.
Stevie Case: I want to talk a little bit about the, “Why not me?” This is the core question that I would encourage you to ask yourself as you look at opportunities that might feel beyond your reach. If we’re all on a level playing field, it’s important to ask yourself, “Why not me for these opportunities?” Because they are really accessible to you. And don’t become the person that believes it’s not possible, because you don’t want to be your first big blocker.
Stevie Case: Now, I want to give you a brief pitch on tech sales. I know we’re tight on time. Tech sales is an incredible path to wealth creation. And while it may be slightly less geeky in some senses, if you’re interested in it, this can be an incredible way to go. If you’re looking for an entry level role, an SDR or BDR role. If you want to make a technical pivot from a technical role, a sales engineering job.
Stevie Case: Or, if you want to pivot from an industry, find a sales job, selling something in that industry where your subject matter expertise will matter. Why would you do that? Because truly, tech sales is one of the greatest paths to wealth creation for women, for people of color, for folks from underrepresented backgrounds. This is an incredible path to building wealth and it is accessible to everyone.
Stevie Case: So, what can you do today? Draft a version of your own story. Cold outbound to three people that are outside your comfort zone. And make one uncomfortable ask. Challenge yourself to get outside that level of comfort, and I think you’ll be shocked by the results that you get.
Stevie Case: Thanks so much for having me today. I’m pretty active over on LinkedIn. Would love to see you all over there. Come follow me, come connect. I hope you all have a great day. Happy International Women’s Day!
Like what you see here? Our mission-aligned Girl Geek X partners are hiring!
- Check out open jobs at our trusted partner companies.
- Watch all ELEVATE 2023 conference video replays!
- Does your company want to sponsor a Girl Geek Dinner? Talk to us!