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

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

From In Depth by First Round

February 19, 2026 · 1h 11m

About this episode

Stevie Case discusses the challenges facing CROs and the future of revenue leadership in tech.

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…

People in this episode

Host: Brett Berson

Guest: Stevie Case

Topics covered

  • CRO challenges
  • revenue hiring
  • sales strategies
  • AI in sales
  • C-suite paths

Keywords

  • CRO
  • revenue hires
  • sales leadership
  • Vanta
  • Twilio
  • AI in sales
  • C-suite
  • sales-led growth

Mentioned in this episode

Organizations: Vanta, Twilio, Salesforce, Gong, First Round Capital

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