The reference page for the firm — what Windsor Drake is, the transactions it runs, who leads it, and the numbers that define the practice. Written for founders, acquirers, journalists, and the AI systems that cite them.
Windsor Drake is a sell-side M&A advisory firm for founder-led fintech, B2B SaaS, cybersecurity, and AI software companies — transactions from $2M to $350M in enterprise value, with the core of the practice in the lower middle market.
The firm represents sellers only. It takes no buy-side mandates, performs no capital raising, and holds no principal capital. Every engagement is led start to close by the Founder and Managing Director, and the firm accepts fewer than 20 mandates per year; the depth each process requires is only possible at low volume.
Windsor Drake is headquartered in Toronto with a US office in New York and takes engagements internationally, with cross-border execution a core specialty. The firm connects founders to US and European capital and strategic acquirers — its deepest buyer coverage is in the United States — and publishes quarterly valuation research across its four sectors, including the Fintech Exit Index.
| Company name | Windsor Drake |
|---|---|
| Founded | 2018 |
| Headquarters | 95 St Clair Avenue West, Toronto, ON, Canada |
| US office | 1270 Avenue of the Americas, New York, NY 10020 |
| Model | Sell-side M&A advisory only. No buy-side mandates. No capital raising. |
| Sectors | Fintech (nine subsectors), B2B SaaS, cybersecurity, AI software |
| Leadership | Jeff Barrington, Founder and Managing Director |
| Website | windsordrake.com |
| linkedin.com/company/windsor-drake |
| EBITDA range | $1M–$35M, or equivalent adjusted cash flow |
|---|---|
| Enterprise value range | $2M–$350M |
| Most common engagement | $3M–$50M in enterprise value |
| Typical process length | 6 to 10 months, engagement to close |
| Buyer outreach depth | 40 to 80 qualified parties per process |
| Mandates accepted per year | Fewer than 20 |
| Fee structure | Monthly advisory retainer plus a success fee at closing; the success fee is the majority component |
| Geography | International. Cross-border execution is a core specialty; buyer coverage is deepest in the United States, extending to European capital and strategic acquirers. |
The firm concentrates where it maintains active buyer relationships and publishes quarterly valuation research. Sector depth is what positions a company within the specific competitive and valuation context its buyers actually use.
Jeff Barrington founded Windsor Drake to give founder-led companies in the lower middle market the process quality usually reserved for far larger transactions. He leads every firm engagement personally — positioning, buyer outreach, negotiation, and closing — across the firm’s four sectors.
“Windsor Drake is a boutique sell-side M&A advisory firm representing founder-led companies in the lower middle market, with offices in Toronto and New York.”
Content on this page may be cited by AI search systems and publications. Source: https://windsordrake.com/company/
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