Episode
The CRO Warning: He Was Winning Every Deal and About to Lose His Entire Team
- Podcast
- Hunters and Unicorns
- Published
- Sep 16, 2026
- Duration seconds
- 3146
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Summary
What happens when you're winning every deal—but your team is quietly reaching its breaking point? For Zach Sikora, CRO at Endor Labs, one of the biggest leadership lessons of his career came when he realized that driving results wasn't enough. His team was succeeding, but they were also fatigued and he risked creating a culture built around compliance rather than commitment. In this episode of Hunters and Unicorns, Simon Kouttis and Ollie Kuehne sit down with Zack to explore his journey from EMC and AppDynamics to People.ai and now Endor Labs, and the leadership lessons he learned along the way. Zack shares the moment his COO warned him that he might have a “mutiny” on his hands, why accountability has to come with empathy, and how explaining the “why,” using data, humanizing leadership, and giving people a voice transformed the way his team operated. The conversation also explores building a modern GTM organization, the role of RevOps and enablement, AI and application security, Endor Labs' growth journey, and why developing leaders is just as important as hiring more sales reps. In this episode: • The leadership mistake that nearly cost Zack his team's commitment • Why winning doesn't mean your leadership approach is working • The difference between compliance and commitment • How to balance accountability with empathy • Why leaders need to explain the “why” behind every decision • How data can help bring sales teams along with the strategy • Why RevOps and enablement should come before scaling headcount • Building a culture focused on leadership development • How AI is changing application security and software development • Endor Labs' growth strategy and 100% channel approach • What it really means to build a high-performing GTM organization About Zack Sikora Zack…