Go To Masters Show · 2026-04-24 · 21 min
Matt Jacobson has spent 30 years in finance, investment banking, corporate strategy, venture investing, and the last 12 building and scaling venture-backed companies as CFO and COO. He's developed a simple framework for how careers and organizations grow: learning, doing, building. And in his telling, none of those phases ever fully ends. In this episode of GoToMasters Finance Fireside, Matt breaks down what it actually means to build sustainable finance operations at a high-growth SaaS company, getting org structure right before anything else, assigning real ownership rather than tasks, and compounding small improvements week over week until the gap between where you started and where you are becomes undeniable. He's equally direct on AI. Not hype, not magic, treat it like a junior analyst. It needs good prompts, constant correction, and a human who knows when the output is wrong. But when it works, it buys back the 15 and 30-minute chunks of time that add up to hours of strategic thinking you couldn't access before.
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