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:

Why early revenue hires fail
What a top 1% CRO actually does
The scaling mistake Stevie made by copying Twilio's playbook at Vanta
Why Vanta remains 100% sales-led at every segment
AI vs. humans in go-to-market

References:

Where to find Stevie:

LinkedIn: https://www.linkedin.com/in/steviecase/

Where to find Brett:

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson

Where to find First Round Capital:

Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast

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