Why Our First Acquisition Was an Operations Company

I’ve spent my whole career building revenue. More than $100 million of it. And in all that time, I never once bought another company — because acquiring a business takes a kind of conviction I hadn’t felt until now.

Last week, that changed. The Whisper Group acquired Upwell Strategies, a done-for-you operations firm, and its founder, Caitlyn Wells, joined us as Chief Operating Officer.

If you’re waiting for the glamorous reason, there isn’t one. And that’s exactly the point.

Here’s what we’ve learned advising women toward their exits: the thing that costs them at the table is almost never revenue. It’s operations.

Founder after founder came to me ready to sell. They had the revenue. Some had healthy profit. And then we’d open the hood. No documented systems. No standard operating procedures. No data room a buyer could actually walk into. Revenue is vanity, profit is sanity — but clean operations are what a buyer needs to close a deal. When they’re missing, a buyer either walks or knocks the price down, and the founder is the one who pays for the mess.

I knew this because I’d lived the other side of it. The woman who ran operations for my own business built systems so clear that when she went on maternity leave, the work didn’t stop. Her team of freelancers kept everything running — because her SOPs were that good. That was the moment I understood what I actually had in front of me. It wasn’t one talented operator. It was a repeatable machine.

So we bought it.

I’ll be transparent about the structure, because I want more women to see how these deals actually work. This was, at its heart, an acqui-hire — we acquired the business and its founder came with it. We brought Caitlyn on full-time as COO. She received equity in The Whisper Group plus a payout tied both to the business she brought with her and the business she can grow inside our operations practice. That structure does two things at once: it gives her every reason to stay and build, and it protects our downside, because we’re acquiring real, existing revenue, a proven freelance team, documented SOPs, and products we can now offer our own clients on day one.

That last part matters. Caitlyn now leads systems and operations for our private advisory clients — the founders who are one to two years out from a sale. The exact people who used to come to us with the revenue and none of the readiness. Now readiness is something we build for them.

I talked with my co-founder Maggie, and with Caitlyn, about sharing this so openly, and we were all in. Here’s why I’m telling you all of this. Acquiring a company felt, for most of my career, like something other people did. Bigger people. People with a playbook I hadn’t been handed. It isn’t. It’s a strategic move available to you too, and the best acquisition might not be the flashy one. Sometimes it’s the operator quietly keeping the whole thing running.

That was mine. And I’ve never been more sure of a decision.

— Carrie