Go To Masters Show · 2026-04-11 · 17 min
Samantha Joswick is the Senior Manager of Sales Operations at H2O.ai, where she owns the full GTM engine: compensation, deal desk, analytics, and systems. Before H2O.ai, she spent several years at Adobe working on product-level comp plans for the global digital marketing sales organization, and led end-to-end compensation at Intermedia Cloud Communications. In this episode, Samantha talks about how she fell into sales ops by accident, spotted a quota overlap at Adobe that leadership was dismissing as rep complaints, and used data to prove it was structural. She shares her framework for comp design: start with the math, but don’t worship it. Use quantitative models as guardrails, then layer on qualitative context from the field to figure out what’s actually sustainable. She also covers how owning deal desk changed the way she thinks about incentives across the full deal lifecycle, where AI adds real value in sales ops (and where human judgment still has to stay in the loop), and her three pieces of advice for anyone building a career in the space: get close to the field, respect the data without worshiping it, and think in systems.
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