One Side of the Table
Windsor Drake does one thing. We represent owners selling founder-led and family-owned companies, and we do not do anything else.
We run no buy-side coverage, hold no lending relationships, manage no capital, and maintain no research franchise for hire. There is nothing on the other side of the ledger to protect, which means an owner never has to work out whose interest the advice is serving.
That exclusivity is also why the firm knows the buyers cold. A bank that covers ten sectors and both sides of every transaction is spread across a hundred buyer sets. We track one: the strategic and financial acquirers who buy fintech, payments, B2B software, cybersecurity, and AI software companies in the lower middle market. We know what they paid, what they walked away from, and what they are hunting this quarter.
Leadership
Jeff Barrington founded Windsor Drake and leads every engagement the firm accepts. He directs the firm’s research program, is the author of its transaction database and quarterly valuation work, and is cited in Reuters, Forbes, PYMNTS, Carta, and Seeking Alpha on technology M&A.
His view is that founders lose money in the space between a headline number and a closing, not in the negotiation over the headline number. Structure, escrow, working capital pegs, earnout mechanics, and the diligence requests that are really price retrades in disguise. Windsor Drake is built to contest that ground.
He works from New York and Toronto and is reachable directly by any owner considering a sale.
- Sector coverage Fintech, payments, B2B software, cybersecurity, AI software
- Published work Windsor Drake quarterly research, the Fintech Exit Index, and working papers indexed under ORCID 0009-0003-3662-3787
- Contact Full profile · Request a conversation · LinkedIn
The Platform Behind Every Mandate
Senior attention is the promise every boutique makes. What separates one from the next is what sits behind the banker when the process starts.
Process
A documented 145-step sell-side process governs every engagement, from preparation through closing. Nothing in a Windsor Drake mandate is improvised.
Proprietary Data
An internal transaction database of 256 tracked deals between $5M and $500M, built and maintained by the firm rather than licensed from a vendor.
Buyer Intelligence
Buyer lists assembled from tracked acquisition behaviour and stated theses, not purchased contact files. We approach acquirers who have shown they buy what you built.
Published Research
47 sourced reports on valuation and M&A activity across 23 sub-sectors, public and free to read, with working papers under permanent DOI.
Specialist Bench
Quality of earnings, tax structuring, and transaction counsel coordinated through firms selected for each mandate, and managed by us rather than handed to the client.
Cross-Border Reach
North American and international outreach runs on every process. The best buyer is frequently not the closest one.
Research That Levels the Table
Founders sell once. The buyers across the table transact constantly, and they hold the information advantage on valuation, on structure, and on what a business like yours has actually changed hands for. That asymmetry is where owners lose money.
Windsor Drake publishes against it. The firm maintains a sourced database of 1,459 market events across 23 sub-sectors, including 256 tracked transactions, and has published 47 research reports on valuation and M&A activity. The market intelligence database and the research library are public, sourced, and free to read.
The research is not marketing. It is the same material that sets pricing expectations and buyer targeting on every mandate. An owner should walk into a negotiation knowing at least as much as the party trying to buy the company.
New York and Toronto
The firm works from New York and Toronto, and runs processes into the United States, Canada, the United Kingdom, and Europe.
The right buyer for a founder’s company is frequently across a border, and a process that reaches only the obvious domestic names leaves money on the table. Cross-border outreach is standard on every mandate rather than an upgrade.
