The CRO Warning: He Was Winning Every Deal and About to Lose His Entire Team

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 Sikora is Chief Revenue Officer at Endor Labs, with leadership experience at EMC, AppDynamics, People.ai, and Endor Labs. His experience spans high-growth technology, enterprise sales, go-to-market strategy, and revenue leadership, with a strong focus on building teams and developing leaders. About Our Sponsor: Big thanks to Aurasell for sponsoring this episode. Aurasell is an AI-native GTM platform designed to intelligently automate every aspect of the sales cycle from prospecting and deal management to forecasting and coaching. Subscribe to Hunters and Unicorns for conversations with the leaders building, scaling, and transforming high-growth technology companies. #HuntersAndUnicorns #ZachSkora #EndorLabs #SalesLeadership #GTM #RevenueLeadership #SalesManagement #SalesStrategy #AI #Cybersecurity #B2BSales #leadership Timestamps: 0:00 — Trailer 1:28 — Welcome & Introduction 2:43 — When It Started to Click as a Leader 4:18 — Accountability With Empathy — The Turning Point 5:48 — How He Actually Implemented Change 7:47 — From Compliance to Commitment 8:31 — Leaning on Mentors Through the Hard Moments 9:09 — The App Dynamics Story — A Baptism of Fire 12:34 — What Made Him Choose App Dynamics Over MongoDB & Medallia 14:52 — Why Dolly Said He Wasn't Ready 16:05 — The Rise to Third Line — Zigs, Zags & Getting Passed Over 18:11 — How to Systematically Build a Team From Scratch