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Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)

Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028.

In today's episode, we discuss:

References:

Timestamps:

00:00 Why early revenue hires fail
02:23 Who to hire at $5M in revenue
04:16 Coin-operated sellers vs. long-term builders
05:57 What excellence looks like in the CRO role
07:44 Metrics, confidence, and velocity
12:04 Should CROs lead sales?
14:39 From shy seller to revenue leader
16:36 Learning to scale at Twilio
17:44 "There is no CRO playbook"
19:58 Stevie's scaling mistake at Vanta
22:16 Why Vanta stays 100% sales-led
23:16 The value of planning 24-26 months ahead
29:54 When trusting intuition was the wrong call
30:49 Do humans still have a place in the future of GTM?
33:33 Stevie's leadership non-negotiables
36:36 The myth of hiring for industry expertise
40:00 What stays centralized in a 600-person company
47:09 The hidden leverage of a customer's first 30 days
53:42 Why the CRO role will face enormous changes by 2028
58:42 What leaders must do now to stay relevant
01:02:30 Unpacking the CEO-CRO dynamic

Brett: All right. Let's do it. Thank you for joining.

Stevie: Yeah, I'm excited to be here.

Brett: Why do you think that early revenue hires are some of the highest turnover people and roles in all of technology?

Stevie: There are a couple of things that make those first hires very thorny. One is unrealistic expectations. The early sales pre-product market fit sales are truly coming from belief in a founder. Yes, there has to be excitement about the product, but there's a certain amount of trust and faith, and a founder tells a story in a way that builds trust and faith in where it's all headed. Often, that first sales hire is coming in or first leader is coming in and they're expected to replicate that same success. They don't have the authenticity of the origin story. They didn't build the product, so their ability to tell the story the same way just isn't there. So founders trying to pass that responsibility to somebody else is one of those original kind of thorny problems.

Brett: What else can you share about that? So let's imagine a company's at five or 10 million in revenue. Maybe they have a couple of junior sellers that are supporting largely founder-led sales. What else can you say about who is ideal for that role and what would their background have been?

Stevie: You want somebody who is just deeply curious and can ask great questions. The counter-signals that you should be looking for when you're hiring somebody here are if you've got a sales interviewee or a leader interviewee who's asking you to give them some kind of confidence they're going to hit quota, that is a bad sign. You don't want somebody who's showing up looking for a guarantee of safety. You want somebody in that role who's going to swing for the fences. They may have no sales experience, but if they can ask great questions, I'm a big believer that everything really comes back to great discovery, they can probably figure out how to close deals for you.

Brett: One of the interesting dynamics of a lot of great people in sales, they are more coin-operated, and it's an interesting tension with what you're talking about because so much of an early-stage startup tends to be more mission-driven, but also most of the bestsellers actually do care about comp.

Stevie: I do think that there is a line after which you want those coin-operated sales folks. The end of the day, those top 1% CROs understand what the CEO and board are trying to achieve for the company and they are able to take that vision and those top-level goals and translate it down into a go-to-market strategy that realizes those goals. It is different every few months, but you have to be that translation layer between top-level vision and how we're making it happen.

Brett: What is velocity in that context?

Stevie: Velocity is going to be a measure of speed in some form. In simplistic terms, it's how long does it take to close a deal? How long does it take you to action a lead? It's how quickly can your team act on an opportunity once they see it, how quickly can you get a contract out the door, and then how quickly can you onboard that new customer?

Brett: If a lot of the way that you have grown is through being around some extraordinary people, what about the opposite of that? What's the only stuff that you learned that you can't just do it by watching somebody that you just have to be in the seat and figure it out?

Stevie: There's a lot. I think that what has been shocking for me in a lot of ways with the CRO role is there is no playbook. Ultimately, you need to divine the truth of your own business for yourself, trust your data and your instincts and then execute on that, because if you try to run somebody else's playbook in this job, it will always be not quite as good.

Brett: When you think about the role of a CRO in a business that's beginning to scale, so call it 30 to 50 million in revenue, what do you think excellence is?

Stevie: The top 1% CROs have to understand what the CEO and board are trying to achieve for the company and be able to distill those big visions and goals into something a team can actually operationalize.

Brett: On the first point that you made about basically rep confidence, is that something that's a judgment call for you?

Stevie: Yes, and it is more a judgment call to math. There's definitely math that matters here. Win rate is the most obvious place this shows up. But in the early days the way this shows up is when you bring in these early sales hires as a founder. You can feel it when they don't yet understand it, but they don't yet believe it, and you can feel it, but you can't measure it.

Brett: What's a good example from the last year?

Stevie: We are trying to move into serving enterprise customers and found it very hard. It wasn't until we hired a completely separate leadership team, we sectioned off our enterprise organization and we basically said, "You guys are completely separate and you're going to sit over here for a year."

Brett: What do you think is the difference between a top 1% CRO in 2026 and a top 1% CRO in 2028?

Stevie: I think in 2028, everyone will need to be systems first instead of human capacity first. If you can build a system and a human team that are really tightly intertwined and feeding off each other, that's what a top 1% CRO is going to be doing in 2028.