How Not to Lose the Deal You Think You Won - with Ben Bauer

Most reps lose deals in the last mile, after the champion is bought in and everyone assumes it's done. Ben Bauer, VP of Sales at WorkFlex, where he runs a 30-person sales org inside a 40-person revenue team, joins Michael Jäger to break down why deals slip late, and what actually protects them: testing engagement instead of assuming it, and trading discounts for value instead of giving them away. In this episode: ✌️ Win #1 — The homework test: small tasks given on every call to test real engagement, so an at-risk deal shows up before it hits the forecast. ✌️ Win #2 — A discount table that trades a fixed percentage for a specific ask, a case study, reference calls, closing 200K ARR deals at 0-4% discount. 🌱 Fail — Loading the full worldwide rollout into deal one instead of land-and-expand, which slowed deals down without moving the needle. Whether you're leading enterprise sales or building a team's negotiation playbook, this episode gives you a concrete way to catch risk early and stop over-discounting. Connect with Ben: 🔗 LinkedIn: https://www.linkedin.com/in/ben-bauer-sales-director/ 🎙️ Beyond Revenue is hosted by Michael Jäger, Managing Partner at Cremanski & Company. New episodes every Friday. ⏱️ Episode's timestamps 00:00 — Intro & Ben's background at WorkFlex 01:32 — How enterprise sales has changed in five years 02:55 — The 150K ARR deal Ben was sure he'd won 03:34 — The phrase that signals a late-stage deal is at risk 04:22 — Process vs. intuition in closing enterprise deals 06:03 — Win #1: the homework test for deal engagement 07:49 — Win #2: a discount table that trades value, not margin 09:37 — The fail: full rollout vs. land-and-expand 12:48 — Key takeaways