Why 90% of CROs Will Fall Behind in the Next 2 Years

• 90% of CROs fall behind by 2028 — systems-first replaces human-capacity-first.
  • AI-native cos hit enterprise wall; legacy SaaS watching upstarts — both need hybrid.
  • Enterprise won’t self-serve by 2030; decades of cloud migration still incomplete.
• Next-gen CROs come from growth-ops/rev-ops/GTM-eng, not traditional sales tracks.
  • Case hired a GTM systems architect reporting directly to her — not under DevOps.
  • 20+ siloed SaaS tools are unworkable; unified systems architecture is the moat.
• Vanta runs 100% sales-led at 600 people — trust requires human-to-human interaction.
• Playbooks are anti-patterns; every biz requires bespoke strategy from first principles.
  • Vanta mistake: applied Twilio’s aggressive hiring playbook without segmenting demand.
  • 6–8 months of pain hiring junior reps for what proved to be complex mid-market.
• Hire Renaissance reps with curiosity + humility; industry-expert playbook-bringers fail.
  • Red flag: candidate seeking quota guarantees. Green flag: equity-over-commission mindset.
• First 30 days post-sale = highest-leverage retention window; frame it as 2-week sprint.
• CRO ≠ VP of Sales — generalist owning top-line revenue, not leading sales execution.
  • Operates on 24–36 month horizons; enterprise seller ramp alone is 6–12 months.

Stevie Case (CRO, Vanta), interviewed by Brett Berson (First Round Capital) · 2026-02-19 · Read on review.firstround.com