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Vanta CRO Stevie Case is on Executive Function this week to unpack how revenue leadership is evolving in the AI era. “In 2028, CROs will need to be systems-first instead of human capacity-first. That's not to say we won’t have large go-to-market teams, but we’re going to have to have CROs who know both sides of that equation. And I think less than 10% of current CROs are capable of making that transition.” Stevie Case is no ordinary revenue exec. A former pro gamer, she found her way into sales when a mentor took a chance on her, climbing her way up as a sales leader at Twilio before joining Vanta as CRO. She sat down with First Round Partner Brett Berson to dissect how she operates as CRO today, and how she thinks her role is going to change over the next few years. She shares: - What founders get wrong about early sales hire: Founders filter for pedigree when looking for the first sales hire, when they should be looking for hunger. “A lot of times founders are hiring for someone with shiny logos on their resume. But the right profile for a first sales hire in your company is probably not that big logo person. You need what we call a Renaissance rep, somebody who’s more creative, more entrepreneurial. They're not necessarily going to have the prettiest resume.”
- Why “Midwest assassin” is such a powerful seller persona: "We've got this Midwestern vibe of people at Vanta who feel like they're outsiders and have this hunger," she says. To find those people, Stevie asks candidates to describe a time they had to grind to get an outcome they wanted, personal or professional, playing close attention to how they tell that story. “When people tell you the story of something they had to really work hard to achieve, you either hear somebody who is ultra-confident and tells you how everything went right, or somebody who can own the things they did wrong."
- Why the next generation of CROs will be technical: Stevie says CROs in 2028 won’t necessarily have a profile like hers. “You're going to see people who have enough exposure to sales, but also are technical and get systems. It could be someone with a growth, RevOps or GTM engineering background, and it won’t necessarily be somebody who came up through 10-plus years of selling.”
We’ve got a lot more interviews lined up in the coming weeks. Here are some of the incredible execs you’ll be able to learn from: - Chris Degnan, former CRO at Snowflake
- David Singleton, former CTO at Stripe
- Katie Burke, COO at Harvey
- Sheila Joglekar Vashee, CMO at Figma
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