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Stevie Case is the Chief Revenue Officer at Vanta, the $4B leader in trust management and compliance automation. Since joining in 2021, Stevie has scaled the company from sub-$20M ARR to north of $100M, navigated 40+ copycat competitors, rebuilt both pre- and post-sales engines, and led Vanta’s expansion from SMB into enterprise. A former world’s first female pro gamer turned tech sales leader, Stevie previously held senior roles at Twilio, where she helped grow the enterprise business to a $1B run rate.
Discussed in This Episode
- How Stevie’s path from pro gamer to CRO shaped her competitive edge
- Early-stage chaos at Vanta and the signs of undeniable product-market fit
- Battling over 40 copycat competitors with value selling and a “CIA” competitive squad
- Why execution, not first-mover advantage, is the only sustainable moat
- The challenges and lessons from scaling SMB sales and moving into enterprise
- Building go-to-market experiments before committing product investment
- Transforming post-sales into a growth engine and driving net retention up
- Stevie’s view on AI in revenue operations and personal productivity
Episode Highlights
00:00 — “Every business is subject to the laws of physics and math… Execution is the only moat.”
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=0
03:07 — Stevie on becoming the world’s first female pro gamer and how competitiveness fueled her career.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=187
06:25 — The undeniable product-market fit that convinced Stevie to join Vanta.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=385
14:02 — Facing 40+ copycat competitors and learning that flashy marketing can’t beat sustainable growth.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=842
16:23 — Transitioning from transactional selling to deep, value-based discovery using MEDDPICC.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=983
18:30 — Creating Vanta’s “CIA” Competitive Intelligence Agency to win back customers.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=1110
26:10 — Launching the experimental enterprise sales team and the patience it took to scale it.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=1570
47:08 — Rebuilding post-sales into separate customer success and account management functions.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=2828
50:56 — Vanta’s next big GTM bets: platform sales, public sector, and deeper enterprise expansion.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=3056
53:27 — How Stevie is using AI in revenue operations and her own work life.
Watch: https://www.youtube.com/watch?v=vIzHgCgTrAU&t=3207
Key Takeaways
- Execution really is the only moat.
Being first-to-market didn’t save Vanta from 40+ copycats. What did? Relentless operational discipline: faster iteration, sharper value storytelling, and a dedicated Competitive Intelligence Agency to win head-to-head battles. - High product–market fit can mask structural weaknesses.
Early Vanta had sky-high inbound demand and “one-call closes,” but no CRM discipline, no forecasting, and a purely transactional sale. Stevie’s first challenge wasn’t growth, it was installing the plumbing to make growth sustainable. - Going upmarket takes years, not quarters.
Vanta’s enterprise motion started as a six-person experiment that took two+ years before becoming predictable and scalable. Stevie budgeted for 50% quota attainment in Year 1, treated wins as bonus revenue, and resisted pressure to “over-forecast” the new segment. - In GTM, “prove it before you product it” can work, but it’s risky.
Instead of waiting for the perfect enterprise-ready product, she ran a GTM-led experiment to validate the market. Only after proof points did Vanta invest millions in product to support the motion. Most founders should reverse this sequence to avoid randomizing product roadmap. - Pricing battles are won with quantified value, not discounts.
To beat low-cost copycats, Vanta shifted from feature/price comparisons to ROI math—quantifying revenue unblocked, resources saved, and time to value. This justified a premium position even against “half-price” clones. - Morale is a GTM metric.
Team confidence was as critical as pipeline coverage. Segmenting teams, matching talent to motion, and keeping quota attainable were treated as strategic levers, not “soft” culture work. - Post-sales is the second growth engine.
To move net retention from ~100% toward enterprise-grade levels, Stevie split Customer Success (retention) from Account Management (expansion), hired a killer post-sales leader, and built a quota-carrying expansion motion. This took another 18+ months to pay off. - Build for the platform, not just the hero product.
Once the core compliance product matured, the next frontier was selling adjacent products (vendor risk, customer trust, access reviews) as standalone offerings. This required dedicated teams so reps didn’t default to the “easy sell.” - Patience + sequencing = compounding growth.
Nearly every major Vanta GTM win (from upmarket expansion to post-sales transformation) took 18–30 months to fully bear fruit. The through-line: start small, measure, iterate, then scale. - AI isn’t replacing sales, it’s rewiring it.
At Vanta, AI now touches almost every revenue workflow, from CRM updates to pre-call prep to onboarding agents. The goal isn’t replacing reps, it’s freeing them to focus on high-value work. Stevie’s advice: invest in AI and in your people so tech amplifies human impact.
Recommended Books
- Endurance by Alfred Lansing — A leadership and resilience classic about Shackleton’s Antarctic expedition
- Amp It Up by Frank Slootman — A masterclass in scaling with urgency
- The Qualified Sales Leader by John McMahon — Tactical guidance for high-performance selling
- The Challenger Sale by Matthew Dixon & Brent Adamson — Framework for leading with insight in sales conversations
Referenced
- SOC 2 Compliance: https://www.aicpa.org/soc4so
- MEDDPICC Sales Methodology: https://meddpicc.com/
- Archer (GRC software): https://www.archerirm.com/
- OneTrust: https://www.onetrust.com/
- Diligent: https://www.diligent.com/
- MetricStream: https://www.metricstream.com/
- Piper by Qualified:https://www.qualified.com/
- Trustpage (acquired by Vanta): https://trustpage.com/
Guest Links
LinkedIn: https://www.linkedin.com/in/steviecase/
Host Links
- LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
- X (Twitter): https://x.com/sophiebuona
- Newsletter: https://thegtmnewsletter.substack.com/
- Website: https://gtmnow.com
Where to Find GTMnow
- LinkedIn: https://www.linkedin.com/company/gtmnow/
- X (Twitter): https://x.com/GTMnow_
- YouTube: https://www.youtube.com/@GTM_now
- The GTMnow Podcast: https://gtmnow.com/tag/podcast/
Thanks to our Sponsor: Qualified
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The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
GTM 158 Episode Transcript
Stevie Case: 0:00
Every business is subject to the laws of physics and math. It looks magical from the outside. Every one of those businesses on the inside felt like chaos. We had 40 plus copycat competitors. It was wild. Execution is the only moat. Nobody cares if you were first.
Sophie Buonassisi: 0:39
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Sophie Buonassisi: 1:22
Today on the podcast, Stevie Case, CRO of Vanta. Vanta just raised a $150 million Series D and is now valued at over $4 billion. Stevie took the company from SMB to enterprise, battled over 40 copycats, rebuilt both pre and post sales engines and continues to lead revenue at the unicorn. In this episode you’ll learn early growth decisions, her first hires, her systems, what she deep prioritized, how she tested and scaled to enterprise, how Vanta beat over 40 copycats with pricing strategy, value selling and a CIA competitive squad. How they drive expansion and why execution is the only moat. We’re proud to be an early believer in and backer of Vanta as an investor. All right, let’s get into it. Stevie, welcome to the podcast. Thank you, so excited to be here, so excited to have you, and I mean what perfect timing with all the momentum that Vanta’s experienced. Huge congrats to you on the raise.
Stevie Case: 2:18
Thank you. I feel really lucky. We’re still having a lot of fun.
Sophie Buonassisi: 2:22
That’s the goal right. You can scale and have fun at the same time. That’s when you know that’s right Incredible. Well, take us back a little bit. You know, maybe even before you joined Vanta, you’ve got an interesting background. Love to unpack that a little bit and how that led you to Vanta.
Stevie Case: 2:41
Yeah, I’ve got a very non-traditional start to my background.
Stevie Case: 2:45
So I started at well.
Stevie Case: 2:47
I started out in college thinking I was going to be a lawyer and I was pre-law poli-sci doing that path and I kind of fell in love with video games and ended up becoming the world’s first female pro gamer world’s first female pro gamer.
Stevie Case: 3:07
And that was a long story, long series of events, but there are some common threads and that early beginning as a competitive gamer really put me on this path towards making games, which games are really just software at the end of the day. So then I was a product manager and ultimately ended up getting offered an opportunity to become a salesperson. Ultimately I ended up getting offered an opportunity to become a salesperson, learned how to do that and over time my portfolio started out as 100% video game companies and became more and more mainstream tech. And years later here I am and I think honestly I look back and it seems a little crazy like it’s a path that doesn’t make a lot of sense on paper, but there are absolutely common threads. Path that doesn’t make a lot of sense on paper, but there are absolutely common threads and my intense competitiveness is probably the single unifying thread from start to finish.
Sophie Buonassisi: 3:53
I love it. I always think we think about careers too linearly in a way, so there’s always a common thread. It’s more of an ecosystem than one linear path.
Stevie Case: 4:03
Absolutely. I’m a big fan of really leaning into things that are uncomfortable and I love to challenge myself and love to grow. And you know, if I had set out and designed a career early on that was only made of things that I knew about at the time, I wouldn’t have gone very far. You know, I grew up in Kansas City, kind of outside of Kansas City, in the country. I had no exposure to business, I had no exposure to a lot of things, and so I’ve been really lucky to get these opportunities where I’ve been able to expand the universe of what I am, what I even know about and what I get to be in the room to talk about. And so I’ve done that. I try to find those little edges that are a little more unknown or maybe a little more uncomfortable, and I tend to embrace those and sort of dive right in.
Sophie Buonassisi: 4:55
Incredible and you go from smaller towns pro gamer product manager to Vanta. What was Vanta’s revenue and go-to-market setup when you joined?
Stevie Case: 5:06
Yeah, we were much smaller so Vanta. Today you know we’re north of a thousand people. When I started we were less than 200 people. We were single double digits of millions in revenue, digits of millions in revenue. So like pretty early on the journey when I joined I just started with North American sales only. So when I joined on day one I had about 20 people on my team, mostly sales people, and it was very early days. There was a ton of excitement. It was super clear. There was this very intense product market fit, but from a go to market perspective, not a lot of structure. It was 100% inbound, not using CRM in a meaningful way, no forecast cadence, like you know it was. The vibes were high but the structure was not really existing yet. So I kind of liked that. It was a. It felt like the Wild West of it at that time.
Sophie Buonassisi: 6:12
Hey, better than the opposite. Right, that’s right, that’s wrong. The vibes are high. All the structure can be brought into place. Yeah, what made you believe that it could scale to be an $100 million plus company?
Stevie Case: 6:25
Yeah, you know I really I struggled with that question because I think it’s easy to look back and say, oh, I saw this thing and it was so obvious. I don’t think that’s often true. And there were some things at that point with Vanta that made it clear that the long term potential for the company was massive and the biggest of those was, honestly, just the product market fit was off the charts and you know people debate what that means or like how do you know you’ve got product market fit? What I can tell you is people were coming inbound at a wild clip and when we would get on the phone with founders we were seeing one call closes. We were seeing just these like oh my gosh, please give it to me now, because you are solving a pain that is so intense and so significant. And at that time our first use case was helping founders get SOC 2 compliant for the first time. And so they were coming to us and saying I have a customer deal and it’s requiring this customer’s requiring that I have a SOC 2 audit complete and that I can give them the report to get the deal done. So it was revenue blocking and I really liked that because you know people only really buy for three reasons. Right, it’s either going to grow revenue, it’s going to reduce costs or it’s going to reduce risk. At the end of the day, those are the only three reasons people buy things and of those, growing revenue is a much more compelling reason to buy than some of the other reasons. So to have that as our primary motivator was huge. And so to see there’s this like really intense pain. It’s a revenue blocker.
Stevie Case: 8:12
There’s a lot of inbound interest and in that process of getting to know the company, one of the things I did was one of the salespeople gave me a demo, so I got an AE to give me a demo. Salespeople gave me a demo, so I got an AE to give me a demo. And you know it was fascinating because it was, in some senses, the demo was super simple. The sales process was super simple. There was nothing. There were no, there was no like over the top sales magic to drive these deals to close. It was like that compelling of a product. So for me, that was the like okay of a product. So for me that was the like okay, this is very real and we can clearly sell more of this. There’s a lot of demand. The thing that I questioned and this came later was sort of like where does it go from there? And that became the big question of the next era.
Sophie Buonassisi: 9:02
And was there a moment early on when you had that question in your mind, where you thought you might have made the wrong call?
Stevie Case: 9:11
You know I don’t know that I ever felt like I made the wrong call, but there were some times that were very, very hard. You know, even in the beginning, as I was debating joining, you know I talked to Andrew Reid from Sequoia, who’s on the board Vanta, and you know I was asking him sort of like where does this go from here? Like this is obviously great, we’ve got good product market fit, founders love us, but we’re selling to very small companies and we’re selling very small deals. And you know I’ll never forget him saying this was like a Sunday night, as I was trying to like make this decision Sunday night at like 11pm or something, and I’m on zoom with Andrew and I’m like it’s a great wedge, but like to what? And he said I don’t know, but it’s a hell of a wedge and like there was like something in that. And you know, like the recognition, I was like okay, I actually can roll with that. Like I am totally good with ambiguity, I can, I am a big believer, I love to bet on myself and I think Christina, the founder of this company, is brilliant, like I want to bet on her. So the bet was we’ve got something really great and a lot of product market fit. We’re going to figure it out.
Stevie Case: 10:27
And that became like my first 18 months. So there was a lot of work. We had a lot of copycat competitors. We had like a whole thing to do in that first 18 months and then we also had to figure out where we were going as a company in the future. And you know, in that first 18 months there there were some extremely hard times. You know, we were in a revenue rut for a long time where three or four quarters in a row revenue didn’t really grow. And when you join as the chief revenue officer and you can’t grow revenue, it’s not good. So I wouldn’t say I thought I made the wrong choice. Necessarily I thought maybe they made the wrong choice. I was definitely.
Stevie Case: 11:09
Yeah, I mean, at the time, though, I was like I don’t, I can’t, I can’t crack the code, like I’m showing up every day trying to figure out how to make revenue go up and to the right, and like I cannot crack the code and I’m like trying everything I can think of. So you know, we did it. After about 12 months, things started to inch up into the right and then, about 18 months in, it was like okay, okay, we figured this out. We figured it out. I figured out how to get revenue to go up into the right, but, man, it was not easy. It was not easy.
Sophie Buonassisi: 11:47
And I feel like those are the common sentiments you hear from anyone in the early days. It’s easy to see Vantageous Series D now and think, wow, that’s incredible. But there were people in the trenches yourself and others, christina and everyone just just you know working day in and day out to make it go up into the right, so really it’s a testament to that.
Stevie Case: 12:06
I mean, I think that that’s for me, the biggest lesson, because you look back on this and it’s like, okay, it’s an obvious success and I just don’t know that.
Stevie Case: 12:17
That is true pretty much anywhere. You know, you look at all these companies Figma IPO’d this week and you listen to what they went through and incredible product, but it wasn’t linear. You know, it was hard and that was of those first 18 months. I think the biggest lesson in it was every business is subject to the laws of physics and math and while it looks magical from the outside and like there’s fairy dust and it’s just happening, and like revenue showed up and the growth was off the charts, it is so true that, like every one of those businesses on the inside felt like chaos, had to grind so hard, hit so many obstacles where they couldn’t figure it out or it didn’t make sense. And the proof point that I like to take for that with Vanta is that we had, at one point, 40 plus copycat competitors. Wow, it was wild and this is one of the reasons I was brought in as CRO is we had, you know, vanta was the first to market. Christina created this market and this concept of the product brought it to market first. We then had several companies see the product market fit and go, oh, we can build that. So they, you know, in some cases went off and like, built an offshore copy and like a third party dev shop and and then came with flashy marketing and we’re like, oh, we’re Vanta, just half the cost. And we went through this entire phase where, you know, it felt to us and, I think, to some in the market, like some of those copycat competitors were winning.
Stevie Case: 14:02
And what I learned through that process? I learned a lot through that process, but one of the biggest things I learned is that you can fool people with marketing for a little bit and you can use that as a cover to create a ton of momentum. But every business is still subject to those same rules, the same math. You’re still. You still got to figure out how to get your net retention to be positive. And on the up and up, you still got to figure out how to get your net retention to be positive. And on the up and up, you still got to figure out how to drive real sustainable growth. You still have to build a go-to-market engine. And you know, flashy marketing and software built cheaply offshore, it doesn’t really get you there. So you know I’m grateful for the lesson. It doesn’t really get you there, so you know it was a I’m grateful for the lesson. We you know we we have pulled away from the pack and that has been incredibly gratifying but was not easy.
Sophie Buonassisi: 14:52
Incredible, I think I mean more than ever. Now. There’s copycats popping up and it’s a common challenge for other companies, for other founders, for early stage go-to-market leaders, for other companies, for other founders, for early stage go-to-market leaders. How would you advise others against that? You know you’ve combated 40 plus other copycats.
Stevie Case: 15:18
How do you win? Yeah, well, I mean, I am a big believer that execution is the only mode. So you know, nobody cares if you were first, nobody cares if you originated the market or you know that you’ve been in it longer. They just want to know that you are going to give them the most value and that they are going to be well taken care of and, ultimately, that you’ve got the best experience that’s going to help them achieve their goals. Like that is all customers care about. So my advice to folks who get into this situation because it is so common now you’ll see there’s a successful business Immediately. People go out and build copycats and sometimes that number two ends up winning, and there are some key things you can do in there to head it off. So you know that focus on execution at the heart. The things you got to do. One is put your head down and start going faster. You know, use it as an opportunity to say, okay, there’s something here we need to now speed up and up our game. So you got to really get tighter on your execution. A couple of the key tactical things that I think really make a difference. One is you really have to focus on value.
Stevie Case: 16:23
This was the big transition that we made as a go-to-market organization in my first 18 months is we went from a inbound transactional sale. We used to say it was kind of like do you need a pen? I have a pen. It was very, very sort of we know what we have is valuable. You need the thing? Here’s the thing. Discovery-wise, we were doing a simple version of Bant. It was just like super, you know Bant, here’s the demo. Great, here’s the order form. We had to move from that to a really different value based sale with much deeper discovery. So we had to get really curious about why our customers were buying and why they were interested in us, what the pain was. So train the team on MedPick and really started to enforce that and like dive deep into the art of discovery, which is something I’m super passionate about. It’s like anytime I work with founders or anybody trying to build a sales team, my number one piece of advice is like learn how to do great discovery. If you do that like, it’s hard to go wrong. Everything else is kind of extra. But if you do great discovery and you’re super curious and you ask those second and third level questions, you’re you’re going to be on a great path. So that’s one.
Stevie Case: 17:36
Two, then, was to quantify the value of our platform. So it wasn’t just here’s the software, here’s the features and functions. Do you want to buy it? It was, okay, let’s understand the pain in your business. What are you trying to solve? Okay, this is blocking a deal. What’s the deal worth? When do you need to get the deal done? What are the resources you have to take this project on? Let’s start to quantify that.
Stevie Case: 17:59
And then we were able to tell a story of the revenue that we could unblock, of the resourcing we could save, the time we could save, and we were able to then compare to those cheaper competitors in a very favorable way, even though we are a premium solution. We were able to prove it with math that we were delivering more value for every dollar. That focus on value is at the heart of it. And then, from there, there’s like a lot of little tactical things we did beyond that value transformation.
Stevie Case: 18:30
Things like we created a competitive takeout squad and they weren’t on quotas, they were just on a takeout target. So they became our experts on these competitors and they learned them inside and out and they just developed the perfect talk tracks called them the CIA, the Competitive Intelligence Agency, and this squad of folks. They were doing their own deal, so they were going trying to like, rip customer logos and they’d go down all the logos on the competitor’s website and try to take them away. They would also get on calls with the rest of the sales team and be that voice of like here’s how you win and here’s what we know and here’s why we know we’re a better solution for you. So there was just a lot of tactics in there and at the end of the day, it was all about building confidence that what we were saying was true we have the better solution, we can deliver more value and we’re going to give you a better experience.
Sophie Buonassisi: 19:26
And that was one of the challenges that you faced in your first 18 months the 40 plus copycats. Take us back to the beginning Now. What was the state of revenue? And then you mentioned the go-to-market engine. Where it was. What were your first moves from a go-to-market standpoint to actually scale?
Stevie Case: 19:41
Yeah, I mean, in those early days the state of revenue, honestly, was unclear. One of the biggest challenges I had at the very beginning is that we had no measurement, and this is actually one of the biggest mistakes I look back at, because I came I came from Twilio where I was mentored by our CFO, george Hu, who at his core, is really an analyst like so deeply, deeply math driven I. That is how I lead a team as well. It’s very math driven. But when I arrived at Vanta, we didn’t have the. We didn’t have any analytics infrastructure, there was no measurement. I could not see anything and while I pushed to build that function and that team, I kind of accepted the no. When I got the no and I was told oh, we’ve got a product analytics team, use what they’ve got, it’s fine. I accepted that and that is probably the single biggest mistake I made when I look back on it, because it meant I went about a year without really being able to see what was going on in my business and it led me to make some incorrect decisions along the way, because on arrival, you know, one of the first pieces of advice I got was you need to hire like there’s a ton of demand. We’re not serving that demand adequately. Like hire people. So I went out and I hired a bunch of SMB sellers, like very junior SMB sellers, because at the time the business looked like a very down market business. And you know, the thought at the time was we can hire junior sellers at you know a fairly low cost and they can still be effective because our win rates are off the charts. But I couldn’t. I couldn’t measure anything. So I was going on instinct and advice and what we found was we brought those people in and won.
Stevie Case: 21:36
The competitive landscape shifted and our win rates went down and we found that the sale was actually more complex than it appeared to be from the outside and one of the things under the covers was that the customer base of prospects were a little more complicated than we thought. It wasn’t just sort of down market tiny startups and founders. There was like enterprise mixed in there. There was like some interesting kind of blend. There was like enterprise mixed in there. There was like some interesting kind of blend. And so these SMB like first time sellers were struggling.
Stevie Case: 22:12
So for the first time we had folks come on and like miss quota, and that was rough. So, going back to that, it was like that was my first mission was hire. And then I hired and it didn’t work. And not only did it not work, we had people join that didn’t hit quota. It obviously diluted the inbound lead flow.
Stevie Case: 22:28
So then you’ve got people that have been here a long time who were like kind of with not a ton of effort, doing like 300% of quota, who are now like maybe sort of making number and maybe not consistently and, as you can imagine, that like crushes the spirit of a sales team For sure. So it was like this very tough moment and there were a lot of lessons in there. For me, number one was never compromise on your measurements, like you have to be able to see what’s going on before you make real decisions, otherwise you are bound to fail because you’re going to make assumptions and you’re going to get it wrong. Number two was really like confidence in a sales team matters more than a lot of other things and keeping morale high and confidence high is fundamental to a winning culture. So lots of lessons learned in there. But you know we recalibrated and changed the plan.
Sophie Buonassisi: 23:22
And where did you pivot from there? What were the most defining go-to-market shifts after that point?
Stevie Case: 23:28
Yeah, the next big one was we had to really recalibrate. At that point as a business. A couple of things had become clear. One was I had gotten the talent profile wrong, so we had hired the wrong kind of folks, and to me that is one of the worst mistakes you can make, because these are people’s careers and you’ve just hired them into a job that they’re probably not set up to succeed at. So, like on a human level, that was kind of devastating. So we had to recalibrate on that. We knew we had to up level the talent.
Stevie Case: 24:07
The second thing we learned through that is, you know, I did not own marketing at that time and we had sort of made this growth plan together and we were going to double the size of the sales team and marketing had agreed to, you know, double the inbound pipeline, because at that time marketing was responsible for 85% of the pipeline. Well, not only did I get the hiring profile wrong, marketing was not able to double pipeline. So we hired all these folks wrong profile and then we did not feed them and we did not have the wherewithal to really drive outbound at scale yet. So we ended up in this position where we had a team that wasn’t getting enough inbound, wasn’t really able to close as much of what they were getting as they could before. And then, you know, we had to make some tough decisions. So we scaled down the size of the team a bit recalibrated, started to build in more measurements, we up-leveled in marketing and we decided to sort of give it a second go, but in a much more math-based way. So this time we, you know, locked hands and had an agreement that was math-based and we started to go forward with a little bit more senior talent.
Stevie Case: 25:27
We went a little more slowly and we started to, instead of like just making big bets and like hiring a bunch of people to go do something, we started to get a little more incremental. So in go to market, for example, you know, we started hiring a slightly different profile of person. We just hiring a slightly different profile of person, we just hired a few, we saw how that went and then we would incrementally add a little bit more. So it was a much more measured approach. We also took that realization that there was a little bit of enterprise and mid-market in our pipeline and what I wanted to do was start to go after that in a meaningful way. So we broke out a team for the first time.
Stevie Case:26:10
We segmented. Basically we had just had a sales team. There was no segmentation before, so segmented, built a team that was specifically tasked with working the sort of like lower mid-market to small enterprise leads. Started small with that, but that was the first time we really broke into two teams, two segments, and then we started to think about that opportunity a little differently. That muscle obviously is extremely different. The sales cycle looks very, very different than the down market one, so we wanted to create the space for them to go after that. So that was one of the next big inflection points was that split of like okay, this isn’t just a business that sells to startups, we’re going to actually go after something different at the same time.
Sophie Buonassisi: 26:52
And it sounds like the signal for that was you had inbound in your mix and when you created this team, was it experimental? Were you fairly confident that this would work and be your wedge to go up market?
Stevie Case: 27:05
It was experimental. It was experimental and you know, the thing that I saw was there was enough inbound from mid-market and enterprise in the pipeline that I knew there was something there, but I, like I did not know enough about what that thing was Like. We knew the use case down market was this you know, first time compliance for founders and we had then expanded the platform and we had added other frameworks so we were supporting things like ISO and HIPAA and GDPR. So we were kind of expanding with founders as we went up market. We just did not know. We did not know what was there and there was a whole space up there, it turns out, called governance, risk and compliance where these so we were starting to there compete against a totally different cohort of companies.
Stevie Case: 28:08
So legacy platforms like Archer and One, trust and Diligent and MetricStream these companies that, like frankly, I’d never heard of and we started to see them in deals and it was a tiny team to start. It was very much an experiment. I set the expectation that, like this is going to take time to work and we need to do the right thing by the team, which means, like giving them a little more ramp, giving them a little bit more buffer running, more spiffs, like giving them more space to learn, because we don’t know what we don’t know. But they did. They started to build a little momentum and you know our original head of sales, he took this on as a project to help us build this upmarket team and, like that small team started hitting numbers. So we started growing it and, you know, just started trying to kind of learn and like trying to learn even the vocabulary of that upmarket buyer, which was extremely different from that of the founders we had been selling to.
Sophie Buonassisi: 29:10
Because it was experimental and that’s great that you got traction. But how did you forecast that?
Stevie Case: 29:16
Yeah, you kind of can’t Fair enough. That in and of itself was something we had to get comfortable with and this has carried through the journey. So when it started as an experiment, you know, one of the agreements at our leadership team level was this is an experiment and the same math can’t apply. It’s not fair to take AEs who are going into a segment we’ve never sold into, we don’t even really understand what the market looks like, we don’t know the dynamics, we don’t know what the sales cycle is going to be, and then hold them to some artificial standards. We did put them on quotas, but then we really tried to do right by them. Frankly, we didn’t, at the top line, count on the revenue. We just, you know it was extra, it was bonus and we have continued to build that way. You know, the second year we did that it’s like okay, there’s something here. Then we built it into more of a true enterprise team. But you know, in a normal sales org you’re going to forecast that that team is going to attain a healthy amount of the rolled up quota. You know, 70%, 80% depends on the segment. With this enterprise team, you know we started out the first year and we said, we are only going to count on them hitting 50% because we just don’t know what we don’t know. So we’ll apply some math and we’ll test against it, but we’re going to set expectations low and then we’re going to work to take care of our people along the way and make sure they all are getting, you know, taken care of for helping us figure out this new segment. But as a business we can’t forecast it. You have to get comfortable with that and I think this is one of the biggest mistakes that people make. When they enter a new segment, or even, honestly, when founders make a first sales hire, they feel like, oh, I have to put this person on a quota and it needs to be an industry standard quota, and if they don’t hit that fairly quickly, things are wrong. It’s a huge mistake because you just don’t know what the right math is and if you don’t create the space to figure it out, you’re going to be doomed to failure.
Stevie Case: 31:24
You know I work with a lot of small companies. Worked with one recently and they told me a story I’ve heard a million times, which is they had an early sales team. They were paying that sales team a lot of money, and this is true often when businesses start they’re like, oh my gosh, salespeople make a lot of money and it makes them uncomfortable, like these salespeople are making a lot of money, they’re not hitting their target. So what this founder did was he fired that sales team and he hired a way more junior, cheaper sales team and then put them against a quota and he said, looking back, he’s like that was probably a mistake.
Stevie Case: 32:00
Yes, that was a mistake. Just because you’ve got expensive salespeople and they’re not quite hitting quota, that doesn’t necessarily mean your solution should be get cheaper salespeople. You’ve got to figure out how to give them the space to get to productivity and in the case of moving up market, that could take years. That might not be a one quarter or two quarter thing, that might be a two or three year thing. So you got to have the patience.
Sophie Buonassisi: 32:25
Great advice overall, with the patience and what time frame were you when you started this upmarket experiment? What year are we looking?
Stevie Case: 32:34
- This was like six months into my tenure, so we’re looking at like mid 2022. Like this is early, early in my tenure at Vanta. So we’re now three years in to that journey.
Sophie Buonassisi: 32:47
How long did it take for you to gain true enterprise traction from that experiment mid-2022?
Stevie Case: 32:54
From that point to get real enterprise traction two years, maybe even a little more. You know we had wins Not to say we didn’t have wins but there’s a difference between getting these sporadic kind of lumpy wins and getting to something that can actually scale. And we hit that point where I felt like this team has scalable success towards the end of last year. And that’s the point at which it’s like OK, we believe that we can hire new reps and know how long it’s going to take them to ramp and be relatively confident that we can give them enough pipeline and that they can hit a reasonable percentage of their quota. And if you can do that and you can put more reps on the team and you can repeat that playbook, then you know you’ve got something that can scale. And that does often take years and it did. It took two, two and a half years for us. And now that we’re there, it’s phenomenal and they will be, you know, a huge percentage of next year’s target. You know there are a material percentage of this year’s target. So we do count on them now to produce. But it doesn’t happen overnight and it doesn’t happen by just like giving people aggressive quotas.
Stevie Case: 34:20
Everything had to change. We now have three segments, but really a down market business and an up market business and those things are radically different. You know they’re selling to different buyers with different collateral, a different value prop, a different value story, the ROI and the way we tell that business value case completely different. And it’s also on a different cadence. You know it’s those enterprise deals are slower, even in our business and our cycles are quite short. But you know it’s a very different thing than like down market. With startups our sales cycle can be 16 days. You know, with an enterprise we’re looking at 70 to 90, in many cases a very traditional cycle we’re looking at more like six months. So you got to make the space for people to do that and it takes time.
Sophie Buonassisi: 35:15
How did you think about evolving product and go to market alignment during that shift?
Stevie Case: 35:21
Yeah, this was big and it is ongoing. This will be a forever thing. At the beginning I felt really passionate about this move up market and so this is a little bit of a I would say this is a little bit of a counterintuitive bet. I went go to market first at market. This is kind of ill-advised. This is actually not the advice I would give most people, but I felt really passionate about it. I thought there was something there and I thought I can build a team and make the math such that I can send the team after this opportunity and we can learn what the market looks like and we can use that to then bring data back to the rest of the organization and show the product team what we think we need to really win up there. So you know, in most organizations you want to go product first if you’re going to make this move. We did go the other way. We went go-to-market first. So what we did is we created this product feedback loop and we really doubled down on sales engineering for the first time, which was not a big function back then for us, but brought in our SEs and we started to develop a point of view on what is the product and what does it need to be for us to win really in the mid-market at that point? For us to win really in the mid market at that point, we had frequent sort of voice of customer meetings with products and we were bringing them really the intelligence on who is this buyer, what software do they use today, what are their needs? And you know, little feature by little feature, we were just asking them to sort of like build this future vision and at that point we were not, as a company, yet committed to that upmarket product. So it was, it was slow and plotting, and we were getting, you know, we were beg, borrow and stealing like resources, and convincing people to ship this little feature here, this little feature. And you know we made progress against it and we were able to then go back and show like, oh, that really landed. And we were starting to do all the things you do like prove that you’ve got a certain number of pipeline dollars against a certain feature request and stack ranking those. And you know it was just a lot of conversation. And at a certain point when we got enough traction and we felt like the product was then sufficient to meet this like larger buyer need.
Stevie Case: 37:49
Then we actually had a formal conversation as a leadership team and this was fun because I worked on this with Chase Lee, who came into Vanta as a VP product. He was the CEO founder of a company called Trustpage that we had acquired. So Chase was super entrepreneurial and he was seeing the same market opportunity as a VP product. He was the CEO founder of a company called TrustPage that we had acquired. So Chase was super entrepreneurial and he was seeing the same upmarket opportunity and so he was on the EPD side of the house and so I kind of like he became my ally in this and he and I made the case we brought this to the leadership team that we should make a real material investment in the millions of dollars, in not just go-to-market for upmarket, but also in the product. And we ended up greenlighting that investment and that was sort of the formal start.
Stevie Case: 38:35
But that didn’t happen until a good year after I had put this little go-to-market squad on going to prove the theory. So it was a long journey to get there, but then we had our proof points and once that was greenlit then we really clicked into. Okay, we now have a business where we’re building two separate things and, granted, it’s one product, but the product experience for a startup founder is very different than the product experience for, like, a CISO who’s our upmarket buyer. So then we were starting to build different engines in the business to take us after those different opportunities.
Sophie Buonassisi: 39:10
Why would you advise founders not to do that and go product first instead of go to market first?
Stevie Case: 39:16
You have to be really sure. It’s really easy to get distracted, especially by inbound lead flow. And this is a common thing because, honestly, every founder what they should be focused on is getting product market fit and then scaling that one thing they do really well. The failure mode for a lot of founders is like shiny thing syndrome, where it’s like we’re doing this one thing really really well, but then, oh, there’s this huge enterprise and they said, if we do xyz and we build these features for them, they’ll pay us a million bucks and like, oh, that would be a big deal for us. And then you get sucked into that and then you kind of don’t account for the fact that there’s like a huge amount of support required and it can really derail you from your core mission. So so I advise founders to go product first, because if you try to force something like that with go to market, you can completely randomize your product development and you can really take yourself off course and end up slowing everything down and kind of kill the product market fit of the thing you had that was working in the first place. So if you’re going to go after a new segment, you need to be really, really sure there’s something there and that was for me that, like the sign that it that it was a bet worth making at the time I did is one I had high confidence in myself and my own analysis and I deeply believed I saw something real. You know, I had seen at Twilio that journey from just serving small companies to serving large Like.
Stevie Case: 40:51
I joined as an enterprise AE at Twilio and they didn’t have an establishment of the enterprise segment when I started we were about 200 million in revenue there and we only had enterprise customers that were like big tech scale-ups, so like Amazon, netflix, these kind of companies, and we had a few but not a ton. When I left six years later, the enterprise business was a $1 billion run rate business and, like in my first couple of years, I personally landed dozens of Fortune 500 logos there. So I had seen that journey and I saw what it looked like at the beginning. When it you know, my first Fortune 500 deal, which at Twilio was a $500 deal, like, I saw that journey up to like $10 million deals and a billion dollar run rate.
Stevie Case: 41:38
So I knew what it looked like and smelled like and I felt, like at Vanta, I smelled it like it was there and I could see that there was something real. So I was making a bet that I could make the math work by pursuing this like tip of the spear strategy with go to market, going up market, because I believed there was something very real there. And I also knew, like you know, it’s a bet, it’s an experiment. If it doesn’t work out, we can recalibrate. I wasn’t confident enough at the beginning to say like, let’s make that multi-million dollar investment on day one. That’s kind of why I went to go prove it out. We sent this squad out to prove it out and luckily, what they found was it was real and we were able to capitalize on it.
Sophie Buonassisi: 42:21
And you probably wouldn’t have had that really high conviction if you hadn’t worn those shoes at Twilio and had that experience firsthand.
Stevie Case: 42:28
Yeah, exactly Because I had the confidence to know what a successful, scalable enterprise business looks like and I had seen the journey to get there and like what it looked like on day one and then what it looked like several years later. So because I had seen that and I knew how the math worked and I knew how to increase deal size. There’s some very like, there’s some mechanics in there of how you can build a package for enterprises from something that started as a small SMB product. So you’re right, I had the confidence of having seen that journey and I believed I could replicate it. So and it’s interesting in retrospect because you know Christina hiring me in the CRO role most of my experience had been enterprise, at least in the most recent years. So she kind of brought me into this very down market business. I know her thesis at the time is she wanted somebody that had seen both, that had seen small, like developers and SMBs, and somebody who had seen enterprise. So I think that that ended up paying off.
Sophie Buonassisi: 43:29
And it all comes full circle that moment when you’re questioning did they make the right decision to? Yes, they absolutely made the right decision.
Stevie Case: 43:37
Hopefully I’ve proven that out by now. I do. I definitely am coming from a place of higher confidence at this point, Like, yeah, it like takes a while as a CRO. This is the funny thing about taking your first CRO gig is everybody’s got advice. Nobody really understands what you’re dealing with.
Stevie Case: 43:54
You know, I remember at the very beginning, actually, the first person that the Sequoia team connected me with was Shant, who’s the CRO at Figma, and I was like, tell me what to do, what is the job? Where should I start? And he had advice. But he’s like every business is so different and that’s what you come to realize is there’s not a playbook, you have to build it for yourself and every is so unique and it’s a super sink or swim job. So like you can get these little nuggets of advice from people but nobody can really tell you how to do the job. You got to figure it out.
Stevie Case:44:33
Most CROs like 18 months is considered success in the CRO role. So I’m three and a half years in feeling good like I survived to tell the tale. But man, it’s hard. So you got to figure out how to get your hands on those gears and on the levers and if you can figure out how to make numbers move. That is really, at the end of the day, the job, and that sounds really simple. But trying to figure out how to move metrics is actually quite hard when you’re. The levers you’ve got are like dozens to hundreds of people and you’ve got all these different dynamics. So I feel very lucky and and here we are several years later and we’re having a blast.
Sophie Buonassisi: 45:13
And we’re north of 100 million. Were there any other pivotal go to market shifts along the journey to get there that maybe we haven’t covered? Oh my?
Stevie Case: 45:20
gosh. Yeah, I mean, the biggest of those, when I look back, was actually not pre-sales, so had a whole journey there, you know, getting new logo revenue going up into the right. But the next big inflection was actually post-sales and you know we had a very down market business. As you can imagine, we sell to founders and you know those like net retention when you sell to startups is naturally going to gravitate lower. If you just look at averages across the industry, you know companies who sell to SMBs are typically hovering around 100% net retention, whereas if you’re selling to enterprises to 120, 140. And as you get to bigger revenue targets and the law of big numbers becomes real, net retention has to go up. So that was my second sort of 18-month journey was figuring out how to get my hands on the levers in post-sales and drive gross retention up, but especially drive net retention up. We had no real expansion motion.
Stevie Case: 46:23
When I started we took on a customer success team. It was a big team. They were being asked to do everything renewals, expansion, customer education and health adoption, like everything and it was totally set up for them to fail because their job was like a hundred different things and you can’t succeed when your job is a hundred different things, and so there was this journey to redefine that team. We broke it into two pieces customer success and account management. That’s evolved. So customer success now owns gross retention, account management owns renewal and expansion. I hired an incredible leader in there, kelly Bray, who leads all things post sales for me, who is just crushing it. And similarly, it took about two years.
Stevie Case: 47:08
We had to build a sales engine in post sales and you know that has been wild and we’ve moved, you know net retention of double digit numbers and that was not easy. And it’s another one where there’s no playbook. Everybody does post sales very differently. It’s even less standardized than sales. So huge learnings in there, and I’ve been so grateful to have Kelly as a partner in it and I think we’re doing some really kind of groundbreaking stuff in post sales today, like where you got to.
Stevie Case: 47:42
It’s one of those unique things too, because it’s not just selling stuff You’ve got, there’s the entire customer experience You’ve got to. You know, ensure customers adopt the platform, that they’re satisfied, that they have a great quality experience, and then you want to tell them more about the rest of the platform and and get them to adopt even more of what Vance has built, cause we built a lot of products over the last year. You know we aren’t just now kind of that core compliance use case. We do vendor risk, we do customer trust, we do questionnaire automation. You know we’ve got this whole suite of products so that post-sales team have to be true experts on the platform, as they are also serving our customers. So big journey there as well and a lot of learning. That was a new one for me.
Sophie Buonassisi: 48:25
What approximate year was that, would you say?
Stevie Case: 48:28
I took that on initially about nine months into my tenure to start and you know I would say the first six months I was really just getting my hands around like how does this even work? Like how is this team working today? Like what are the basics here? Going out and I do anytime I take on something new I go out and talk to as many people as I can, so talking to tons of customer success leaders and account management leaders, just talking to anybody I can talk to to understand how they do it. So it’s about six months of investigation.
Stevie Case: 49:01
Then we started transformation and you know the first transformation was that breaking the team into customer success and account management, so two different functions and that first change was about 12 months after I took on the team and then from there that was a good you know. So it’s been, you know, a couple of years since we made that change and there’s been a lot of incremental change since then. So we’re about two years into the journey and we it took about a year and a half to really see that start to pay big dividends.
Sophie Buonassisi: 49:36
We’re hearing the pattern of starting initiatives and really waiting and having the patience to see it pay off, as opposed to the immediacy. Yeah, so time, yeah, yeah. And Steve, you now, I mean you’re north of 100 million ARR and Series D. Congrats again. What’s the next big go-to-market focus for you and where are the opportunities ahead?
Stevie Case: 49:57
Yeah, I’ve got a couple of big ones over this coming year. So one is really sell the platform and what that means for us is just like when I arrived and we kind of had one sales team and no segments. We now have multiple segments, this broad team, but that broad team is really selling the core platform. The reality is we have shipped a lot of other incredible products. This vendor risk product that’s becoming a true third-party risk product. Our entire customer trust platform. We’ve got these other elements in the platform. We’ve got an access review product. They can in many cases be sold standalone. So now a lot of the mission is let’s go sell those as true standalone products to different buyer personas and it means really creating separate teams and muscles and motions in our go-to-market engine. So that’s a big one. That’s a huge area of investment. We’ve got killer products in these areas.
Stevie Case: 50:56
But again, like the products don’t sort of like figure out how to sell themselves. You’ve got to go figure out how to build a funnel for each one, how do you identify buyers, and then you’ve got to create the space for a team to actually go sell that and not it’s counterintuitive, but like not get weighed down by the success of the core product. So if you give everybody you know the whole platform to sell, they’re going to sell the core thing that sells. Well, they won’t pay attention to, like the products that are emerging. So you got to create space for somebody to focus on just emerging products. So that’s the one big one.
Stevie Case: 51:28
The next big one is really going to be what we’re calling Vanta for government public sector. We just went down this path and just last week got our FedRAMP 20X low authorization, which is a big deal. It’s like the federal government is doing this pilot program to essentially expedite people being able to be fedramp compliant, which now allows them not just to sell to the federal government but in our case it makes it so we can help other companies become fedramp compliant. So they’re sort of like selling to the government and then they’re selling to other companies who sell to the government as well.
Stevie Case: 52:05
Massive opportunity for us. We’re really excited about it and we are committed to that journey to really work in that federal ecosystem. So, building out a public sector function, bringing in leadership there and doubling down on our opportunity there is another big area. And doubling down on our opportunity, there is another big area. And then the third is the continuation of the journey we’re on, which is serving larger and larger enterprises. So we do serve today a tremendous number of large enterprises. We’ve got customers in the Fortune 100. We are selling to not just tech scale-ups but like true kind of old school enterprise logos, and so continuing down that path and serving their needs around governance, risk and compliance is going to be a big part of the mission over the next year.
Sophie Buonassisi: 52:52
Incredible Well excited to see all of that in execution. And, stevie, I’ve got to ask you how are you using AI personally and in Vanta and learning about AI? How are you?
Stevie Case: 53:04
using AI personally and in Vanta and learning about AI. Yeah, we’ve got a couple of big angles here. So I am a big believer in AI. I am very bullish and, honestly, like what we’re doing at the heart of it is sort of remaking the way we think about revenue operations. So historically, revenue operations teams were more system admins, not necessarily builders and folks who wrote code.
Stevie Case: 53:27
We are moving in the direction of building an AI builder function within revenue operations. We’ve already got a team started there. So we are infusing AI into basically every workflow every workflow. So all of the basic things you would think of like updating CRM with AI, delivering pre-call prep notes to our teams with AI all of those workflows now exist. Now we’re starting to think about some next stage use cases, like we’re bringing in an agentic platform to help bring customers through onboarding in a really interesting way. We’ve, of course, infused it in support, where we can really shorten response times and get great high quality responses. So like we’re building it everywhere At the same time, we are making a bet on humans. So I look at AI and go to market as an opportunity to allow our humans to do the higher value work and really up level the way they function. So big investment on both the tech and humans. Personally, I am having a blast with it. I love it. I ended up buying an entirely new laptop so I could experiment and just sort of go wild.
Sophie Buonassisi:54:38
I love it.
Stevie Case:54:40
Oh yeah, I’m actually building an app right now. I’ve been playing around with both Cursor and Replit and having a ton of fun with that. I’m, of course, obsessed with ChatGPT and use it for basically everything in my life for everything from fun things and sort of entertainment to interpreting my lab work when I can’t get ahold of my doctor to. I actually did my taxes this year with the help of chat GPT. Highly recommend TurboTax plus chat GPT magical combination totally worked for me. So you know, I I’m a believer. I know there are a lot of skeptics and they’ll say, like you know that you should not, but I don’t know. I’ve had a great experience and I’m bullish. I think that you know. Ai gives us the opportunity to do things that are more human and can take out that minutiae, and I’m enjoying it.
Sophie Buonassisi: 55:41
What about the other side of the coin from AI? Are there any books that you’ve particularly enjoyed and that you’d recommend to anyone listening?
Stevie Case: 55:49
Yeah, it’s a great question. So right now I am reading a book called Endurance, not a business book but kind of a leadership book. You know it’s great. It’s about this shipwreck and kind of the way that this crew led themselves out of this very dire situation where they were shipwrecked in, of the way that this crew led themselves out of this very dire situation where they were shipwrecked in a very bad situation Book that was given to me by Varun, the COO and founder over at Clay Great crew. So that’s what I’m enjoying right now.
Stevie Case: 56:18
I do a lot of business books as well, as you can imagine. So it’s kind of nice to get a little respite from the business books. And there, you know, you got to do all the classics, the like. You know the, the Slootman books, you know the qualified revenue leader, always a fan of the classic challenger sale, like I still think that lands. I still go back to that structure. So, yeah, all all of those are great, but I’m trying to take a break it’s summer and read something a little more off the beaten path.
Sophie Buonassisi: 56:50
Yeah, yeah, fair enough. And where can people find you if they want to get in touch or follow your journey?
Stevie Case: 56:57
Yeah, they can find me on LinkedIn, so I am posting on LinkedIn super active, love to connect there, so come find me Awesome.
Sophie Buonassisi: 57:05
We’ll pop it into the show notes, Stevie. Thank you so much for joining. Congratulations again on the Series D, and we can’t wait to see the continuing progress that you and Benta have.
Stevie Case: 57:13
Thank you so much. It’s been great being here.
Sophie Buonassisi: 57:16
Awesome To everyone listening. Thank you for joining us and we’ll see you next week.
