The Orchestration of Enterprise Deals - with Thomas Cser

Most enterprise deals don't die because of the product. They die because of internal alignment debt, over-engineered selling teams, and a champion with no budget. Thomas Cser, Head of DACH Revenue & Growth at Stripe — and former enterprise leader at SAP, Salesforce, and ServiceNow — joins Michael Jäger to unpack what it actually takes to move complex, multi-stakeholder deals from interest to decision in 2026. In this episode: ✌️ Win #1 — Go vertical or go generic: how building real industry depth — the right talent, the right language, the right use cases — accelerates trust, shortens cycles, and shifts conversations from "software features" to business impact. ✌️ Win #2 — Focus beats motion: why ruthless ICP discipline and geographic focus outperform opportunistic deal-chasing — and how long it actually takes for the compounding effect to show 🌱 Fail — The over-orchestrated deal: what happens when too many people get involved too early and why a small, sharp team with a strong AE beats a swarm every time. Whether you're running enterprise sales or trying to scale a complex GTM motion, this episode gives you a sharp lens on what separates precision deal-making from hope-based chaos. Connect with Thomas: 🔗 LinkedIn: https://www.linkedin.com/in/thomascser/ 🔗 Stripe: https://stripe.com 🎙️ Beyond Revenue is hosted by Michael Jäger, Managing Partner at Cremanski & Company. New episodes every Friday. ⏱️ Episode timestamps 00:00 — Intro & Thomas's background 01:53 — How enterprise selling has fundamentally changed in 20 years 04:55 — The real source of complexity most teams underestimate 06:33 — Early warning signs a deal is drifting 09:07 — What separates orchestrated from chaotic deals 09:57 — Win #1: Going vertical to win enterprise trust 13:27 — Win #2: Focus, focus, focus — ruthless ICP discipline 17:31 — Fail: Over-orchestrating deals with too many people too early 19:56 — Episode recap & key takeaways