Gary Miller here, wondering why every startup that says they’re “not looking to sell” somehow ends up with new owners three months later.
So I’d been working this deal since last summer – a growing fintech startup, about 200 employees, perfect fit for our business software. The CEO, Sarah, was fantastic to work with. We’d had maybe six calls over four months, really building something solid. She understood exactly how our software would help them scale their operations, and we were talking about a $180K deal to start, with expansion potential as they grew.
I’m thinking this is going to close by end of quarter. Sarah and I have that good working relationship where she’s actually returning my messages, her team is engaged, and the budget conversation went smoother than usual. You know how rare that is these days.
Then I get a LinkedIn notification that stops me cold. Sarah’s updated her profile – she’s now “Former CEO” and there’s a press release about the acquisition. Some big financial services company bought them out. Completely blindsided me.
I reach out to Sarah immediately. She’s apologetic but realistic: “Gary, I’m sorry, but everything’s on hold. New ownership means new priorities, and honestly, they already have enterprise software relationships locked in.”
Of course they do. The acquiring company probably has contracts with our biggest competitor that go back years. All those months of relationship building, all those discovery calls where we mapped out their exact needs – none of that matters to the new owners.
I ask Sarah if there’s anyone I should connect with on the new team. She gives me a contact, but warns me: “They’re probably going to want to standardize everything on whatever they’re already using. It’s just how these things work.”
She’s right, naturally. I reach out to the new guy, and he’s polite but clear: they’re consolidating all their subsidiaries onto their existing platform. Doesn’t matter that our software is a better fit for what Sarah’s team was building. Doesn’t matter that we’d already done half the implementation planning. Corporate standardization trumps everything.
The kicker? Three weeks later, I see Sarah’s started a new company. She messages me: “Hey Gary, we should talk in six months when we’re ready to look at business software again.”
So now I’m back to square one with Sarah, except she’s got no employees and no budget yet. Meanwhile, that $180K deal I was counting on for Q4 just evaporated because of market changes I couldn’t have predicted or controlled.
This is the reality of business software sales in 2025 – external disruptions can kill your best deals overnight. You can do everything right, build great relationships, understand the customer’s needs perfectly, and still lose because of forces completely outside the sales process.
At least Sarah and I have a good relationship for her next company. In this business, sometimes that’s all you can salvage when the market shifts under your feet.
Leave a Reply