The Raindrop that Evaporated by Choice

Last month, I closed my first 7-figure deal after months of persistence and creative problem-solving. Today, I want to share the counterpoint - when walking away is your smartest move.

This week I walked away from a deal that was ready to pilot.  

The Sunk Cost Trap

When I joined Windsurf, I had 8 named accounts. “Raindrop” - my smallest by revenue and headcount, was a great logo and fit squarely in our ICP.  Over the course of 4 months, I met with 10+ people including their CPO, went onsite, earned their trust for Slack / text connections, and even got invited to speak at their conference.

Last week our primary point of contact said the magic words: “we’re ready to pilot.”

99% of AEs and Founders would double down.  Instead, I’m choosing to walk away.

The MEDDPICC Reality Check

Six months ago, my only focus was on generating pipeline. Now, with Devin in my toolkit and a territory refresh post-acquisition, I need to be ruthless about ROI and prioritization.  As tempting as it is to continue chasing Raindrop, I chose to slow down and use MEDDPICC, the qualification framework some of my former colleagues used to mock as “old school.”

The analysis was brutal:

[M]etrics: No clear project goals beyond “provide flexibility to our developer community.” Translation: we're headed for procurement purgatory, even if the pilot succeeds.

[C]hampion: My “champion” was actually a coach at best. He'd never run a procurement cycle at this company, couldn’t identify pilot users, and had zero urgency due to competing priorities.  I speak more about the dangers of coaches in Founder Mistake #2.

[I]dentify Pain: When I asked for 10 names of developers with specific pain points we could solve, he went silent. No identifiable pain = no compelling event.  I am not starting a pilot unless I know there is a cohort that are pounding the table for a clear painpoint we can solve uniquely well.  

The Uncomfortable Math

Let’s play devil’s advocate.  Here’s what happens if I ignore the MEDDPICC gaps:

The math is painfully clear.  Qualify out for now.  

Conclusion: Walking Away = Walking Forward

I sent the breakup note yesterday. I view this as a gift to my Coach as it frees up his time away from a journey that will not drive transformative impact in its current form. 

For me, MEDDPICC saved me from the sunk cost fallacy that kills quota attainment.

There’s a chance their CPO comes back with real metrics, a true champion, and quantified pain. Until then, I’m focused on opportunities where the stars align.

The hardest lesson in sales isn’t learning to close - it's learning when not to.

Note: Opinions and commentary in this article are solely mine and do not represent the views of Windsurf or Cognition in any way. Raindrop is a pseudoynm to anonymize the name of the prospect.