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. Our mandates are founder-led fintech, payments, and technology companies with enterprise values between $5 million and $300 million.
We do not represent acquirers against our own clients, hold no lending relationships, 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 Market Transaction Index and quarterly valuation work, and is cited in Reuters, Forbes, PYMNTS, Carta, and Benzinga 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 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
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Senior Advisors
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Bruce Goldstein advises Windsor Drake’s financial services, fintech and payments work. He has spent more than thirty years in financial services, as a managing director at Keefe, Bruyette & Woods and an initial member of Sandler O’Neill & Partners, later a partner at Milestone Advisors and a founding partner of Middlemarch Partners.
His depth is in the infrastructure of the industry: sponsor-bank relationships and BIN sponsorship, Banking-as-a-Service and embedded finance, loan origination and servicing, and asset-backed funding. He has also been an operator, as a founding partner in a Mastercard issuing business and founder of an online consumer lending company.
- Sector coverage Fintech, payments, consumer lending, specialty finance, bank sponsorship, Banking-as-a-Service, embedded finance
- Contact Full profile · Request a confidential consultation
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Michael Culhane advises Windsor Drake’s consumer, retail, distribution, and business services work. He has spent more than twenty years as a chief financial officer in retail and distribution, across public, private-equity-backed, and family-owned companies in the United States and Canada, with particular depth in strategic mergers and divestitures.
His focus is closing readiness: preparing a company so the transaction completes and the transition holds, the work that matters most when an owner has rollover equity or an earnout at stake. His experience includes the $1.8 billion sale of 189 Zellers stores to Target Corporation, a transaction that required operational wind-downs, inventory liquidation, and lease settlements.
- Sector coverage Consumer, retail, distribution, business services, and other founder-led situations
- Contact Full profile · Request a confidential consultation
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Thom Gunderson advises Windsor Drake’s medical technology work. He spent twenty-four years as a Managing Director and senior research analyst at Piper Jaffray, covering medical technology companies in the public markets from 1992 to 2016, after thirteen years inside the industry at American Medical Systems, including as Project Director.
He is an independent director of Merit Medical Systems, where he chairs the Finance and Operating Committee, and of TransMedics Group, where he chairs the Compensation Committee and serves on the Audit Committee as a board-designated audit committee financial expert. He chairs the Minneapolis Heart Institute Foundation and is an Executive in Residence at the University of Minnesota’s Medical Industry Leadership Institute.
- Sector coverage Medical devices, cardiovascular technology, surgical products, diagnostics, healthcare innovation
- Public boards Merit Medical Systems · TransMedics Group
- Contact Full profile · Request a confidential consultation
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 sell-side process governs every engagement, from preparation through closing. Nothing in a Windsor Drake mandate is improvised.
Proprietary Data
The Windsor Drake Market Transaction Index, covering every major technology sub-sector, built and maintained by the firm rather than licensed from a vendor, with current counts computed on every build.
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
Published research on valuation and M&A activity across every major fintech sub-sector, 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 market events across every major fintech sub-sector, each documented to a primary source, alongside a published research library on valuation and M&A activity. Current counts are computed on every build and published in the Fintech Exit Index. 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.
Where the firm works
The firm works from 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.
