Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)
In Depth
Intro
Brett introduces the In Depth podcast and welcomes guest Stevie Case to start the conversation.
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 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
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