Windsor Drake advises founders and owners on the sale of their companies. Sell-side only, led by senior bankers on every mandate, with offices in Toronto and New York.
Built from the Windsor Drake Fintech Exit Index, with data through August 2026.
View the trackerWhat fintech companies sell for, by era and sub-sector. After the October 2026 Index review, completed deals announced since 2022 sit at a 9.8x revenue median, against 12.1x in 2020 and 2021.
Read the paperIn the press
Reuters, July 2026
Reuters cited Jeff Barrington in its reporting on how tournament demand and Middle East exposure are splitting the earnings outlook for US travel companies.
Read the coverage
Forbes, March 2026
A Forbes Finance Council article on why vertical software is being repriced in the AI cycle, citing Windsor Drake’s SaaS and AI valuation reports.
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Carta, July 2026
Carta quoted Jeff Barrington on fund specialization and the fundraising environment facing emerging managers.
Read the coverageWhat we do
Windsor Drake acts for sellers only. No lending relationships, no buy-side mandates and no capital conflicts. Every engagement is led by a senior banker from the first meeting to closing and staffed with a senior advisor who has completed transactions in the client’s sub-sector.
A confidential, controlled process designed to create competitive tension among 150 to 300 qualified strategic acquirers, private equity platforms and family offices, run across six gated phases over roughly nine months.
How we run a sale
Recapitalizations, minority sales, management buyouts and ownership transitions, each weighed against a full sale before any process is chosen.
Recapitalizations and transitions
When a buyer calls first. We establish what the company is worth, decide whether to widen the field, and negotiate from information rather than reaction.
Responding to an approachBefore any process
Before any process, a 30-day written readout: a price range built from the firm’s transaction data, the acquirers most likely to pay it, and a clear verdict on whether to sell now, sell later, or not sell at all.
About the ReadoutOur thinking
Fintech Exit Index
Verified fintech M&A transactions since 2019, each with primary-source documentation and classified by sub-sector. The reference for what fintech companies actually sell for, available by API.
Payments
Artificial Intelligence
Briefings from Windsor Drake
Which acquirers were active, what they paid, and what changed in the quarter. Four issues a year, written by the deal team.
Thank you. The next issue will reach you when it is published.
The firm
Windsor Drake Inc. is an independent investment banking firm headquartered in Toronto, with its United States headquarters in New York. The firm accepts fewer than twenty mandates a year so that the people who win an engagement are the people who run it.
No lending book, no research franchise and no capital markets desk. Windsor Drake acts for sellers only and has never represented an acquirer against a client.
Fewer than twenty mandates a year. Every engagement is led by the Managing Director and staffed with a senior advisor drawn from the client’s own sector.
The Fintech Exit Index, the Acquirer Files and the Valuation Lab are built in-house and published, because a seller should negotiate with the same data a buyer has.
Founder & Managing Director
Leads every engagement the firm accepts and directs its research program. Formerly Cushman & Wakefield in New York, Toronto, London and Singapore. Quoted in Reuters, PYMNTS, Carta and Benzinga.
Senior Advisor, Financial Services & Payments
Thirty years in financial services, including Managing Director at Keefe, Bruyette & Woods, an initial member of Sandler O’Neill & Partners, and founding partner of Middlemarch Partners.
Senior Advisor, Consumer, Retail & Business Services
Twenty years as a CFO in retail and distribution across public, sponsor-backed and family-owned companies in the US and Canada, including the $1.8 billion sale of 189 Zellers stores to Target.
Senior Advisor, Medical Technology
Twenty-four years as Managing Director and senior medtech analyst at Piper Jaffray. Independent director of Merit Medical Systems and TransMedics Group.
Offices
Canadian headquarters
95 St Clair Avenue WestUnited States headquarters
375 Park AvenueConfidential
advisory@windsordrake.comEvery inquiry is read and answered personally by a senior banker, usually within one business day. The firm runs sale processes into the United States, Canada, the United Kingdom and Europe.