The first time I realised a “big win” could quietly bankrupt a team…
was the day a rep closed a deal everyone celebrated, except the people who had to deliver it.
On paper, it looked perfect:
£100k+ ACV
Enterprise logo
Board-level visibility
Quarter-saving timing
Behind the scenes?
It was the deal that broke the quarter.
Here’s what no one saw happening:
1. The team rebuilt half the product just to satisfy one customer.
Engineering velocity fell off a cliff for 6 weeks.
2. Support volume tripled.
Because the customer was a fundamentally bad fit.
3. Three healthy deals died quietly.
Why? Every resource was protecting the “big win” instead of building repeatable value.
4. The rep who closed it never hit quota again.
Because they were now expected to repeat something that should never have happened in the first place.
Here’s the part leaders miss:
Bad-fit revenue doesn’t show up in Salesforce.
It shows up in burnout, churn, slipped roadmaps, and stalled momentum.
And when we finally analysed the pattern, the truth was painfully simple:
The deals that broke the business looked nothing like the deals that scaled it.
Fixing it didn’t start with pipeline reviews.
It started with one decision:
Stop chasing the deals that drain the business, and double down on the ones that compound it.
Tomorrow, I’ll share the framework we used to make that decision operational, not emotional.