From startup to exit: What fintech founders need to know

Tiffany Haynes is a fintech operator and founder of Illumea Advisory, where she advises founders and growth-stage companies. Previously, she helped scale Fingercheck through a $150 million private equity exit and spent two decades in leadership at Jack Henry. She is also the host of Between Builds.

Founders think exits are won through growth. Buyers know they're won through operational trust.

Acquisition readiness starts with operations, but it extends well beyond the numbers. It also shapes how founders engage with buyers and lead their teams through the deal and the transition that follows.

The last company I helped scale was a bootstrapped, product-led B2B SaaS business. When I was first introduced to the founder and started to see how the business actually ran, I could tell the pieces and parts of a great exit were all there. 

But there were also several gaps that needed closing to allow for more growth. For example, the sales motion was strong, but there was no real marketing engine driving demand. Client support was strong and a key differentiator, but operations didn't have a voice in the product conversation, which meant the company was missing meaningful UX additions the support team could easily flag. Those inconsistencies made the go-to-market loop clunky internally, even as it appeared to be gaining momentum.

My job wasn’t to create momentum; it was to help the company harness what was already there. What the company needed was the operational layer that would keep things going so that when a buyer eventually looked at the business, they'd see something they could believe in and underwrite with clarity.

From my experience, the operational layer is what turns founder-driven momentum into reliable performance. It’s the collection of systems, processes, metrics, and leadership structures that allows the business to operate without depending on the founder’s intuition.

How to know what's needed

When we talk about the operational layer, it can be hard to articulate or even define, which is part of why so many founders skip it or under-rotate on it.

Every company needs something a bit different, and figuring out what that is for your specific company takes time and conversation. One founder I spoke with recently had implemented the Entrepreneurial Operating System (EOS) at his company and felt good about how that was driving organizational clarity and shared goals. The challenge was that the go-to-market and sales motion were still riding almost entirely on his intuition, his conversations, and his own ability to read what the customer needed at any given moment. The intuition was legit. But intuition alone isn't a system, and that's exactly what building the operational layer is meant to do.

Building those systems is one thing. The harder part is making sure every function is working from the same information and priorities. The most common version I see is sales and marketing data that doesn't tie out to finance. A buyer can ask something as basic as how you calculate customer acquisition cost, and the answer can reveal that the sales team and the finance team have been measuring it two different ways. The problem goes beyond the number itself and points to a lack of discipline in how the company defines and measures performance.

This is exactly what a buyer is trying to find out before they put money in. They're not asking to find a reason to pass. They're trying to understand what's been engineered intentionally and what still needs work.

When to know you're ready

Readiness is harder to determine than most operators expect because it requires honest dialogue and a clear-eyed read of both the business and its place in the market.

There are the obvious signals like sales growth, EBITDA bending in the right direction, and leadership stepping up, but past a certain point you have to feel it, and feeling it requires self-reflection and discernment.

Sometimes the numbers look great but the market itself is off, and you would be selling into a window that’s closing rather than opening. Or the business is going well, but the founder is still holding too tightly to the work, which means the leadership team isn't being allowed to fully succeed or fully fail on its own. A team with a clean record of execution and no visible failures is often a team that is still routing meaningful decisions through the founder. Buyers can see that within a meeting or two.

This is also where having a bench of advisors matters. It’s hard to reflect on something you can’t see or exercise good judgment without enough perspectives in the room. Reading the market, pressure-testing the numbers, and knowing whether the timing is right — none of this is something a founder or operator should be doing alone. You need people around you who have seen this happen before and who can help you sense what you can't see from inside the company.

That same discernment matters once buyers actually arrive at the table, because reading the company from the inside and reading the buyer from across the table require similar skills. Most founders I work with don’t realize that strategic and financial buyers aren’t asking the same questions. Creating a solid partnership requires slowing down to understand what each buyer is solving for.

Types of buyers

A strategic buyer is trying to understand where you fit into their existing product set, where you fill a gap, and how much overlap exists with what they already own. Overlap can cut two ways: sometimes it means they are paying for capability they already have, and sometimes it means they are paying to consolidate the market and take a competitor off the board. Either way, you need to know which case you are in, and it’s okay to ask them that question directly while you think through your own narrative and positioning.

A financial buyer has a completely different set of priorities. They want excitement and velocity, scalability that can absorb capital, a much larger TAM in view, and a credible flip in three to seven years. That distinction is cleaner in theory than in practice now, because many PE firms are running platform strategies where the question becomes a hybrid. They might be asking whether the company fits a platform they are already building, and whether the combined entity is ultimately flippable.

The underlying point still holds, though. Regardless of the buyer, the same company and product enter meaningfully different conversations. Founders who do this well know which story they are telling in which room, and they can navigate between them with confidence. Those who don’t often default to the strategic pitch because it most closely resembles how they sell to customers. Then they wonder why the financial buyer didn’t respond as expected.

All of this takes practice, and you won't get it perfect every time. Just make sure you're working on all the versions, not just the one you're most comfortable with. I'm still working on it myself.

Diligence coming due

Due diligence is the part founders tend to underestimate the most, and I know I did. It will feel like an interrogation no matter how friendly the room is, because the data requests are invasive, and the questions are skeptical by design. There will be days when you walk out of a call wondering if these people even like your company. Or you.

This is the part of the process I most want founders to be ready for, because I found it disorienting the first time and I want to spare them that. You're certain of what you've built, and you love it with everything you have. And now it's being called into question line by line, by people who don't know you and don't owe you the benefit of the doubt.

The standard advice in moments like this is some version of "don't take it personally," which is one of the least helpful things anyone can say. Of course it’s personal. You built this. 

What I have come to believe instead is that the work is not to feel less or care less, but to learn to hold two opposing things at the same time. This can be a company you are deeply proud of, and a company that is being formally called into question. It can be both sorrow and joy tangled together. 

The capacity to hold two true things together without collapsing one into the other is one of the marks of operational maturity I have come to respect most, and it is one I struggled to develop and still practice.

Transitioning post-deal

When I was chief people officer at a publicly traded company that did a high volume of acquisitions, I watched newly acquired teams take far longer to settle than any deal model ever assumed. The organization grieves even when the deal was a good one and the company exited on all cylinders. The team you built may have signed up for the company as it was, not as it is, and their experience of the transition will not match yours.

This is also where I have watched the most well-intentioned leadership instincts fail. As soon as you start projecting your version of the transition onto the team with some variation of “this is for the best,” you lose the room. One of the most important disciplines in that season is not trying to talk anyone into seeing it your way.

So if I’m leaving operators with one takeaway, it’s this. The operational layer is what makes an exit possible, but everything you build before the deal is really in service of the people who will be standing in the room with you the day after. Spend time listening and attuning to the team you built with, because they are going to be navigating a season they didn't necessarily choose. And give yourself plenty of time and space too, because it’s hard to process what something means to you personally while you’re also explaining it to others. The work of holding all of that together is real work.

Build the company so the operational layer is ready when you need it. Then bring the rest of yourself to supporting the people involved, because that’s what determines whether the work you put in actually meant something.