Enterprise Deals Are Won Before the Demo | How Enterprise Sales Actually Works, Jaap Boven (Charles)

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.Chapters01:11 – Anatomy of a big-tech enterprise deal (and how to win it)11:04 – Scaling sales from day one at early-stage scaleups23:57 – How outbound sales has evolved26:05 – Lessons learned from M&A28:27 – Using AI in sales today36:35 – Common hiring mistakes in sales38:56 – Advice for GTM operators👉 Follow the podcast for weekly episodes on building GTM from the ground up