Jan 25, 2023 · 1h 0m · news
Stevie Case: World's First Female Pro Gamer; Hiring Tips for Sales; PLG vs Enterprise | 20VC #970 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, Vanta's Chief Revenue Officer, Stevie Case, shares her journey from professional gaming to sales leadership, offering tactical strategies for hiring, structuring compensation plans, transitioning from PLG to enterprise sales, and selling effectively in a down market.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 20.8% of the talking time here. How this is scored →
Harry as informed peer 2.3 Guest teaching 3.7 Guest disagreement 0.3 Harry pushing back 1.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 36:08 Stevie defends finishing her college degree
When Harry bluntly asks why she needed a degree given her career success, Stevie firmly reframes it as a personal challenge to prove her own determination.
Hardest push from Harry ▶ 23:08 Harry questions Vanta moving up-market into enterpriseHarry directly challenges the premise of moving into enterprise sales when SMB was working so well, forcing Stevie to justify the move as additive and experimental.
Biggest teaching moment ▶ 49:30 Stevie reframes slipped deals as discovery failuresStevie corrects common founder and seller assumptions by explaining that deals slipping to the next quarter are almost always caused by inadequate early discovery rather than late-stage timing issues.
Harry holds his own ▶ 49:15 Harry draws on board experience regarding slipped dealsHarry cites his experience sitting on startup boards to challenge the familiar excuse of deals slipping into the next quarter, pushing Stevie to address the root cause.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| How the World's First Female Pro Gamer Entered Sales | 1 | 3 | 0 | 0 | Harry welcomes Stevie and asks about her path from pro gamer to Vanta CRO. Stevie explains her background in gaming, mobile games, and mentorship by Matt Golden. | |
| Embracing Introversion and Vulnerability in Sales | 2 | 3 | 0 | 1 | Harry asks whether Stevie lost her introversion or embraced it. Stevie explains leveraging vulnerability in sales, while Harry shares his own interview technique regarding personal vulnerability. | |
| How Game Design and Product Management Inform Sales Leadership | 2 | 4 | 0 | 0 | Harry asks how game design experience influences sales leadership. Stevie explains software empathy, strategy, and viewing CRO revenue goals as the game score. | |
| Single Motherhood, Proving Doubters Wrong, and Creating Inclusive Environments | 2 | 3 | 0 | 1 | Stevie shares her experience as a single mother while building her sales career and overcoming doubters like John Romero. Harry asks about societal perceptions of mothers in tech and inclusive leadership. | |
| Mentorship and the "Revenue Game" Playbook from George Hu | 2 | 4 | 0 | 0 | Stevie discusses her mentorship under George Hu at Twilio and his operating model. Harry asks her to clarify what playing the revenue game means mechanics-wise. | |
| Navigating the Staggered Transition from PLG to Enterprise Sales | 4 | 4 | 1 | 3 | Harry probes the transition from PLG to enterprise sales, challenging the timing at Twilio and Vanta. Stevie outlines the dangers of comp confusion and explains Vanta's dedicated experiment up-market. | |
| The Founder's Playbook: Hiring and Scaling the Early Sales Team | 3 | 4 | 1 | 2 | Harry sets up roleplay scenarios around early sales hires and playbooks. Stevie breaks down founder storytelling versus sales execution and why every rep must be a hunter in the current macro. | |
| Defining and Testing for Grit: Stevie's 25-Year Degree Journey | 2 | 3 | 1 | 2 | Stevie defines grit and curiosity as key sales traits and shares her 25-year degree completion journey. Harry jokingly questions why she bothered finishing her degree when already successful. | |
| Structuring the Interview Process & What Good Discovery Looks Like | 2 | 4 | 0 | 1 | Harry asks how to structure sales interviews and test discovery skills. Stevie distinguishes between bad box-checking discovery and good curiosity-led discovery that uncovers core customer hooks. | |
| Designing Sales Compensation Plans and SPIFs | 2 | 4 | 0 | 1 | Stevie discusses sales comp design and using activity-based SPIFs to motivate reps. Harry jokes about the British slang meaning of spiff before Stevie explains cash and recognition incentives. | |
| Measuring Long-Cycle Effectiveness, Slipped Deals, and Strategic Discounting | 3 | 4 | 0 | 2 | Harry raises board-level frustrations regarding slipped deals in enterprise sales cycles. Stevie explains that slipped deals stem from early discovery failures and shares how strategic discounting can close deals. | |
| Selling to CFOs and Shifting Value Propositions in a Down Market | 2 | 4 | 0 | 1 | Harry asks how selling changes when CFOs scrutinize every purchase. Stevie highlights the need for multi-threading early and shifting value propositions toward cost savings and risk reduction. |
Statements from this episode (24)
Stevie Case was the world's first female professional gamer
“As the world's first female professional gamer.”
Demonstrating personal vulnerability is the best way to open people up
“The best way to open people up Is to give them comfort with your own vulnerability.”
Sales professionals can show imperfection because buyers buy from people
“Ultimately people still buy from people and you can be competent and also just a flawed human being who is uncomfortable and unsure at Times.”
Being a CRO is ultimately about math and score optimization
“And the math behind it to win being a CRO really is not all that different. You have to adapt constantly. It's very dynamic. You're putting together all of these different elements into a strategy. And ultimately the math has to work and really just the score …”
Workplace bias against mothers remains widespread in tech and business
“It is still very real in many corners. I think the thing that has changed is there are now places that we can work, that we can go where people are more enlightened and they understand that you can be both of those things. You can be in that world of being a p…”
Women should reject the narrative that parenting requires career trade-offs
“The single most important thing is don't apologize. Don't accept this narrative that it's a balance or a trade-off or you're giving something up somehow. It's up to you to define your own narrative, and you don't have to accept that idea.”
Twilio had a $200M run rate at IPO, aiming for $1B
“We, you know, IPO, we were two hundred million dollar run rate. And Jeff had set out this vision of we're gonna get to a billion dollar run rate.”
Combining PLG and sales too early creates customer friction
“You can, but I would caution you against trying to do both right away. I think in the early days of sales, you have to be very, very clear on what is the value prop for the customer and what is that experience. And when you try to combine PLG and a sales motio…”
Enterprise PLG requires sales reps to handle complex customer needs
“But if you're trying to sell into an enterprise, I am Pro-PLG in the enterprise, but you've got to have some sales folks to back it up as well because they always have needs that cannot be automated away.”
SMBs measure compliance speed while enterprise customers measure risk reduction
“So an SMB is measuring How quickly can I complete this process to prove I'm compliant? And a mid market customer is really measuring how much time can I save? How much risk can I reduce?”
Vanta created a dedicated enterprise team with a separate compensation plan
“And so in the middle of the summer, I created a team just to go after those mid-market and enterprise opportunities because it is, it's a very different cycle. So put that team on a different comp plan, gave them a little bit more space and time to experiment,…”
Individual sales reps cannot simultaneously handle SMB and enterprise deals
“I think the thing that goes wrong is when You've got a team focused on one segment and you ask them to dip a toe in the water of another segment. And it's very hard for any one person to both do, you know, high velocity bottom of the market deals and also do s…”
ACV experience matters more than domain knowledge when hiring sales reps
“Of those two, I'd go ACV. I think that it's actually much more important that somebody understand the profile and they understand the mechanics of doing a deal of that size with that profile. They can learn the subject matter expertise in many cases.”
Non-sales executives should participate in sales hiring interview loops
“I think it's actually extremely valuable to get the perspectives of folks who are not salespeople in that process. Just because they haven't sold doesn't mean they don't know what good looks like.”
Whiteboard roleplays expose sales candidates who interview well but fail under pressure
“You put them up at a whiteboard and ask them to do discovery in an uncomfortable situation. That's where a lot of them fall down.”
Sales candidates requiring guaranteed compensation are poor fits for early-stage startups
“Somebody who indexes too hard on those guarantees probably is not a fit in a startup.”
Effective sales compensation plans dictate daily priorities without management oversight
“At the end of the day, what you want out of a great comp plan early days as a founder Is something that is so clear that if a salesperson reads it, they understand exactly what they should spend their time doing when you're not in front of them.”
Sales spiffs should incentivize specific behaviors rather than top-line revenue
“A SPF is going to work best when you tie it to something else that might not be directly tied into how they're incentivized in the comp plan, but it's something you need them to do and is important to the business.”
Slipped enterprise sales deals almost always stem from poor initial discovery
“So many great salespeople suffer from this, and ultimately, this is a failure of discovery. When this happens, you can almost always trace it back to the beginning of the conversation in that deal, and a lack of understanding of some key factors.”
Avoiding CFOs early in the process causes enterprise sales deals to collapse
“The most important thing in an environment like this is that your sellers pull those people into deals much earlier. So the junior sellers approach in these kind of environments is I want to avoid the CFO at all costs. And like in the world of Vanta, I want to…”
Vanta is reprioritizing cost savings over growth drivers in enterprise sales
“The thing that does have to shift as we move forward now in this new environment is that the value drivers that matter are a little bit different. So we're going to have a little more emphasis on cost savings. And efficiency and yes, growth still matters. Ever…”
High-volume cold outbound sales outreach is dead and requires personalization
“Oh, high volume, cold, outbound at scale. It just is brutal. You've got to personalize. People are constantly hit from every angle. You got to give them something meaningful.”
Stevie Case successfully sued her Kansas school board over a banned book
“So I sued my Kansas school district because they banned a book. You know, I grew up in Kansas outside of Kansas City. The school board banned a book because it was an award-winning book, but it had homosexual theme. And I did not feel that was either right or …”
Vanta purchased Clari software despite having an active company budget freeze
“Of course, the tool had to be amazing. There had to be all the value there. They had to prove that value. They showed us so much value before we signed the deal, and then they gave us a great offer we couldn't refuse at the end of the quarter, and we got it do…”