Before Stevie Case was a CRO, she was the first female professional gamer—dropping out of college to compete in Quake and eventually building games in the early days of the shooter universe. That competitive drive never left. It's the same thing that made her the number one enterprise seller globally at Twilio, and it's what's driven her nearly four-year run as CRO at Vanta, where she's led the company's push from a startup-focused compliance tool into a full enterprise trust platform.

In this episode of CRO Stories, Rachael Bueckert sits down with Stevie Case, CRO of Vanta, for a conversation on what it took to move Twilio from inbound-only to outbound, the enterprise hackathon play that blew deals wide open, why she resisted moving into leadership and what changed when she did, how Vanta used sales as the tip of the spear to validate an entirely new market, the counterintuitive bet on human SDRs in the age of AI, and how rebuilding post-sales raised net retention by 18 points.

[00:45] Intro to Stevie Case

[02:00] Competitiveness and stubbornness as career fuel

[03:58] "Why not me?" and overcoming imposter syndrome

[07:02] From Quake champion to college dropout to tech sales

[09:39] Saying yes to discomfort

[11:52] Best seller vs. leading sellers

[14:17] Trusting delayed results as a leader

[14:29] Moving Twilio from inbound-only to outbound

[16:50] The playbook is a hypothesis

[18:43] Why forcing your style on reps backfires

[22:17] Where uniformity matters vs. individual style

[24:03] Q4 2019: 279% of target

[25:47] Managing to the maximum possible outcome

[28:29] The foundational change behind the blowout quarter

[29:22] The Twilio Sandwich: bottoms-up meets top-down

[30:16] Enterprise hackathons and the U-Haul story

[33:50] In-person selling post-pandemic

[35:02] 5x outbound pipeline with human SDRs

[36:00] Building outbound from zero at a 100% inbound org

[38:21] One-call closes and the original Vanta motion

[41:18] Spotting the enterprise signal inside the customer base

[47:33] Sales as the tip of the spear into a new market

[48:16] Bifurcating the business: downmarket vs. upmarket

[49:32] What broke first: quotas, feedback loops, and org design

[50:34] GTM under a product GM for a year

[52:12] Building enterprise post-sales from scratch

[53:19] The Implementation Health Score

[55:10] Scaling into enterprise SDRs, SE, and market education

[58:14] Raising net retention by 18 points

[59:25] The counterintuitive bet on customer success

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CRO Stories: Competing, Scaling, and Making Enterprise Bets with Stevie Case

GTM Science - A show for GTM and RevOps leaders

CRO Stories: Competing, Scaling, and Making Enterprise Bets with Stevie Case