Go To Masters Show · 2026-04-17 · 34 min
Courtney Hickey is the Director of Revenue Operations at ParentSquare, a K12 communication platform serving school districts across the US. She didn't come up through traditional RevOps channels - she started in administrative and legal roles, learned the business by sitting in on executive conversations, and built her way into operations from the ground up. On this episode of the Go To Masters Show, she shares what that unconventional path taught her about designing systems that flex, where comp plans break trust before anyone notices, and why she thinks AI's biggest promise has nothing to do with speed. Why rigidity is the biggest risk in RevOps and why falling in love with the problem beats falling in love with the process The quiet side of comp trust erosion: when the RevOps team can't explain the plan either, you've already lost on both ends Why AI's real value isn't speed but signal quality, and what it looks like when teams build for the wrong metric
Stacey Mangold (Axway) on If a Rep Can't Explain Their Comp Plan in Two Minutes, Something's Broken88 / 100Hadas Sheinfeld (Sisense) on Leading the Energy, Hiring for Grit & Acting Like a Director First60 / 100Caroline Rocha (Just Eat Takeaway) on Designing Comp Across Cultures, AI Myths & Comp Transparency62 / 100Why the Person Running Your Comp Plan Should Be the One Closest to the Pipeline69 / 100
Jelle Berends (Oyster) on Building RevOps From 1 to 65, Why Playbooks Don't Travel & Comp Design