How Investors Evaluate CROs in Funding and Exit Decisions

When venture capital and private equity evaluate your company, sales metrics and execution are under the sharpest scrutiny. In this CRO Summit session hear what investors want to see in your sales organization—and the red flags that make them nervous.

You’ll hear directly from a VC and a PE operator about how they assess ARR, funnel efficiency, CAC payback, win rates, and operating systems, plus how they separate story-driven answers from real data.

The Problem Centric OS

Speakers

• Keenan – CEO, A Sales Growth Company
• Seth Levine – Partner, Foundry Group
• Drew Kiran – Pratice Director GTM, K1 Investments

Key topics covered:

• How VCs and PE investors scrutinize sales organizations at different stages
• Metrics that matter most: CAC payback, funnel conversion, churn, win rates
• Red flags that kill confidence in revenue predictability
• Why storytelling instead of data undermines credibility with investors
• How founders and CROs can prove repeatability and scalability
• The role of operating systems in driving sustainable growth

Chapters

00:00 Introduction & Session Overview

05:20 What Investors Look for in Sales Organizations

12:45 Key Metrics: CAC Payback, Funnel Conversion & Forecasting

22:10 The Dangers of Founder-Led Sales at Scale

31:05 Storytelling vs. Data: What Investors Really Want

41:30 Red Flags: Revenue Concentration, Excuse-Driven Leadership & Messy CRMs

53:00 How Investors Evaluate Predictability and Operating Systems

1:04:20 Audience Q&A: Betting on Early-Stage Unknowns

1:13:00 What Sales Leaders Consistently Get Wrong

1:20:00 Final Takeaways