Sales In The Age of AI: The Playbook from The CROs of Databricks, Windsurf, Perplexity and Owner
We recently completed in-depth conversations with the CROs and VPs of Sales from Perplexity, Owner, Databricks, and Windsurf. Their insights on AI-driven selling come together here as a clear playbook for AI-powered revenue growth.
Top 10 Insights
The AI shift in sales is happening now. Those who adapt first will pull far ahead. After studying four revenue leaders on the front lines, these ten insights stand out as defining success or failure in AI sales:
- AI Creates a Great Bifurcation: Top performers become unstoppable; average reps fall behind.
- AI-Native Hiring is Non-Negotiable: Candidates must already be using AI tools.
- Speed Has Become the Ultimate Moat: AI users move faster than those who don't.
- Technical Sales Teams Hold a Massive Advantage: Deep product knowledge combined with AI is powerful.
- The “People Person” Sales Rep is Dead: Expertise and teaching matter more than charm.
- AI Implementation Demands Continuous Investment: No tool works perfectly out of the box.
- Revenue Models Must Blend Human and AI: Seamless customer journeys beat siloed experiences.
- CROs Must Become Hybrid Team Managers: Leading humans and AI agents is the new norm.
- Attribution Models Will Break (And That’s Good): Focus on total business value, not just commissions.
- Meeting Prep and Pipeline Analysis Are Just the Beginning: True change comes when AI handles direct customer interactions.
Learning #1: The Great Bifurcation – Elite Performers vs. Everyone Else
“AI boosts elite performers much more—it makes the best get better and widens the gap.” – Kyle Norton, CRO, Owner
AI isn't helping average salespeople catch up. Instead, it makes top reps far more productive while leaving others behind.
Evidence:
- Owner sees 3-4x productivity gains, but only from AI-native reps.
- At Windsurf, 7 out of 10 seasoned reps exceeded annual quotas quickly; one closed $1.6M in four months.
- Perplexity serves 5,000+ enterprise clients with just 5 salespeople.
- Research shows AI raises the floor on simple tasks but significantly boosts complex work.
What This Means: Identify your top and bottom performers now. Invest heavily in AI tools for your A-players. For C-players, give them 12 months to improve or consider transitions.
Learning #2: AI-Native Hiring is Non-Negotiable
“A key part of interviews now is: what are you doing with AI? How are you using it?” – Graham Moreno, Windsurf
Great sales skills alone aren’t enough. Candidates must show active AI fluency.
New Interview Standard: “If they’re not AI native, we can’t hire them.” – Kyle Norton
Actions to Take:
- Include AI usage questions in every sales interview.
- Ask for demonstrations of AI tools candidates use.
- Test curiosity about learning new AI applications.
Learning #3: Speed Has Become the Ultimate Moat
“Speed is the new moat. Your competitors are moving faster.” – Dmitry Shevelenko, CBO, Perplexity
Perplexity hit the market as GPT-3 gained power—before competitors reacted.
How to Move Faster:
- Use AI for pre-meeting research on every prospect.
- Automate CRM updates to remove admin delays.
- Deploy AI for rapid proposal and deck generation.
Learning #4: Technical Sales Teams Have a Massive Head Start
“Most of our salespeople are more technical than most. They can code, do POCs, and pilots.” – Ron Gabrisko, CRO, Databricks
Databricks grew from under $1M to over $3B ARR with a technical sales team.
For Non-Technical Teams Selling to Technical Buyers:
- Invest in technical training for sales leaders.
- Hire sales engineers to bridge gaps.
Learning #5: The “People Person” Sales Rep is Dead
“Being a ‘people person’ isn’t enough anymore.” – Kyle Norton
Customers want reps who can teach them something new, backed by AI-driven product knowledge and market insights.
Learning #6: AI Implementation Requires Continuous Investment
“You need to create content and tweak your AI every day, every week.” – Graham Moreno
Success Tips:
- Choose platforms with realistic expectations—get about 50% of what you hope at first.
- Commit to ongoing improvement weekly.
Learning #7: Revenue Models Must Blend Human and AI
“Aim for semi-self-serve with consistent customer journeys across channels.” – Kyle Norton
How To Build This:
- Design systems enabling smooth shifts between AI and human touchpoints.
- Train AI on your top sales conversations to keep quality high.
Learning #8: CROs Must Become Hybrid Team Managers
“My job includes managing both human teams and AI agents.” – Kyle Norton
Key Skills:
- Systems thinking focused on customer journeys.
- Understanding what AI can and can't do.
Learning #9: Attribution Models Will Break (And That’s Good)
“Is your job just to hit sales numbers or to build enterprise value?” – Kyle Norton
Changes to Consider:
- Shift from individual to team-based incentives.
- Measure customer satisfaction and long-term business outcomes.
Learning #10: Meeting Prep and Pipeline Analysis Are Just the Beginning
Windsurf uses AI that joins Zoom calls, answers questions, and sometimes jumps in proactively.
What’s Next:
Success will rely more on finding product-market fit and delivering value than just scaling go-to-market efforts.
The Bottom Line: Act Now or Get Left Behind
These insights come from leaders already living the AI sales future. The time to adapt is closing fast.
Your 90-Day Action Plan:
- Week 1-2: Audit your team’s current AI usage and curiosity.
- Week 3-4: Deploy basic AI tools for meeting prep and CRM automation.
- Week 5-8: Use AI for pipeline analysis and deal risk assessment.
- Week 9-12: Build hybrid human-AI customer experiences.
The future of sales belongs to those who build it. Start today.
For sales professionals looking to sharpen AI skills quickly, explore practical courses at Complete AI Training.
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