In this episode of In the Trenches, Stefan Ross (early operator at Pigment and Celonis) joins Navin to unpack what actually happens when you’re an operator building revenue without a playbook.Stefan has been on the ground at Celonis and Pigment, navigating first GTM hires, early ICP bets, partnerships, and the messy reality between founder ambition and operator execution.We talk about what operators see that board decks miss, why comparison to outliers breaks decision-making, how partnerships actually work (and when they don’t), and what GTM teams should push back on harder.Chapters00:33 – The disconnect between VC's and operators07:49 – First principles for early startup hires13:58 – The most common mistakes founders make22:59 – How to crack the partnerships motion in a startup (Pigment & Celonis case studies)34:25 – Must-have operational habits for sales37:41 – Leveraging AI in business operations48:22 – Advice for sales🎧 Subscribe to the show for more operator-led GTM stories🔔 Subscribe for new episodes every Wednesday, 8:30AM CET

In this inaugural episode of IN THE TRENCHES, Jaap Boven, Enterprise Sales Executive @ charles, shares how enterprise deals are really shaped, reflects on joining tech scaleups DocuSign & Freshworks in their early days, and how GTM operators can influence outcomes before sales conversations even begin.

A grounded, operator-led conversation for founders and early GTM hires navigating complex B2B sales.

Chapters
01:11 – Anatomy of a big-tech enterprise deal (and how to win it)
11:04 – Scaling sales from day one at early-stage scaleups
23:57 – How outbound sales has evolved
26:05 – Lessons learned from M&A
28:27 – Using AI in sales today
36:35 – Common hiring mistakes in sales
38:56 – Advice for GTM operators

👉 Follow the podcast for weekly episodes on building GTM from the ground up