The Upmarket Trap: How to Scale Without Breaking Your GTM
Access the Full GTM Playbook on Moving Upmarket at the end of this newsletter...
Scaling Upmarket is Not Just an ACV Jump—It’s a Whole New Game
You’ve closed a few bigger deals. The Board wants more.
But now your GTM motion is breaking—longer sales cycles, fewer conversions, and your sellers are stuck in SMB mode.
Sound familiar?
Too many teams pour months of execution power into an upmarket transition—only to realize they’ve misjudged what it takes to win in Enterprise sales.
I’ve seen this happen across SaaS, FinTech, and Cybersecurity.
The harsh truth? Most upmarket GTM shifts fail because teams underestimate the complexity involved.
