A founder called me earlier this year and said something I don't hear often enough: "I'm in over my head. I need to build a lean team, solve problems, and execute against our goals."
That kind of honesty is rare. It's also exactly the condition where a fractional COO does their best work.
It took 45 days to get to contract — not because of indecision, but because they were doing it right. Tech partners integrated. Product tested. Beta users signed and ready. They wanted to hand me something worth executing against, not a pile of assumptions.
The first 10 days were heads-down with the team — mapping goals, surfacing fears, sequencing every dependency. We built the go-to-market strategy from the ground up.
Then, right before we pressed go, our payment processor pulled out.
Not a negotiation. Not a technical issue. They were never going to work with us — they just hadn't bothered to say so for two and a half weeks while we built our entire infrastructure around them.
One infrastructure assumption. That's all it took to stop a fully loaded GTM strategy cold.
We had no time to sit with it. We identified seven potential payment partners and started working the list. Three rejected us outright. Two could technically support us, but the margin hit made the business model unworkable. We were down to two options, and neither was a clean fit.
What made it hard wasn't just the rejections. It was the language. Every meeting ended with some version of "we can't support marketplace functionality" — delivered with zero explanation and zero alternative.
For anyone outside payments: all we wanted to do was accept a payment from a customer, send the majority to the service provider, and keep a small platform fee. Turns out that's called a marketplace model. It's classified as high-risk by a lot of processors, and plenty won't touch it. We didn't just need a new vendor. We had to learn an entire industry, almost overnight.
Six weeks behind. Cash burning. Early adopters losing patience.
Here's where it turned. We had two viable partners left. One was a name nobody would recognize — small, scrappy, attentive, willing to work with us from day one. The other was the established player — history, integrations already built, a marketplace offering that matched what we needed almost exactly. We'd nearly written them off.
At the last minute, we found the right person inside that organization — someone who could actually say yes. He scoped a custom solution that fit our model, and just like that, we were back.
We hit our 90-day milestone. Not without scars.
Here's what I'd do differently:
- The biggest name doesn't mean the best fit. We built our entire infrastructure around a household name that was never going to work with us. Reputation is not a substitute for a signed agreement.
- No deal is done until ink is on paper. While a vendor is telling you you're close, ruthlessly pursue every alternative. Hope is not a pipeline strategy.
- Surface your hardest problems first. Whatever a vendor might not like about your business, lead with it. I'd rather know we're incompatible on day one than day forty-five.
- Learn their world, not just yours. We had to become fluent in an entire vendor industry's vocabulary almost overnight. That knowledge turned uncomfortable conversations into productive ones.
- Test your assumptions before you build on them. We were handed an infrastructure assumption that felt settled — because it had never actually been tested under real conditions. The GTM plan was meticulous. The foundation it sat on wasn't. That's the first thing I validate now, before I build anything on top of it.
The best operators aren't the ones who avoid chaos. They're the ones who know what to do when it finds them.