Selling a company is not a transaction most founders will repeat. It rewards preparation, competitive tension, and control of information. Windsor Drake exists to give fintech and payments founders the same caliber of representation that larger enterprises take for granted.
We advise on a deliberately narrow set of engagements so that senior bankers remain involved from first conversation to closing. We do not staff mandates with junior teams and step back. The people who win the engagement are the people who run it.
We frame the equity story around the drivers a sophisticated fintech buyer underwrites: recurring and transaction revenue quality, program and interchange economics, regulatory posture, and the management depth that survives a transition.
Controlled, confidential processes engineered to create competitive tension among a curated set of strategic and financial buyers, without broadcasting a company to the market.
We manage the details that determine whether a headline valuation survives to closing: diligence, structure, working capital, and the terms buried below the purchase price.
The lower middle market is underserved. Bulge-bracket banks decline mandates below their fee thresholds; regional brokers lack the process rigor to run a competitive sale. Fintech founders are left to negotiate against professional acquirers who close dozens of transactions a year.
We close that asymmetry. Every engagement is led by a senior banker whose only objective is to represent the seller: no lending relationship, no research franchise, no capital markets desk with competing interests. The result is advice aligned entirely with the founder’s outcome.
We take on few clients by design, so every founder has our full attention. Selling the company you built is a responsibility we treat as our own.
Jeff Barrington, Founder and Managing Director
Founder-led fintech and payments companies with enterprise values between $5 million and $300 million, evaluating a full or partial sale, generational transition, or institutional recapitalization.
Every discussion is confidential and without obligation. Request a consultation ›