About this episode
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:
Cursor: https://cursor.sh/
Gong: https://www.gong.io/
Salesforce: https://www.salesforce.com/
Twilio: https://www.twilio.com/
Vanta: https://www.vanta.com/
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 i
