Jeff Barrington

From the Other Side of the Table

Jeff Barrington has spent his career building companies and making deals. After selling a business of his own, he joined Cushman & Wakefield, where he worked on complex transaction mandates across New York, Toronto, London, and Singapore.

Since entering the deal business in 2018, Jeff has advised on more than $750 million in technology transaction value and developed the research-led approach that underpins every Windsor Drake engagement.

He founded Windsor Drake to address a fundamental imbalance in the market. Most founders sell a company once. The buyer across the table does it for a living. The firm brings institutional research, disciplined competition, and senior judgment to the founder's side of the transaction.

The objective is straightforward: identify the full strategic value of the business, create genuine tension among qualified buyers, and protect the founder's interests through closing.

Most founders sell a business once. The outcome depends entirely on the quality of the person running the process: their judgment under pressure, their command of buyer psychology, and their willingness to protect the client's interest when it costs them convenience.

The Practice

Jeff advises a deliberately limited number of founders each year on transactions ranging from $5 million to $300 million in enterprise value. Windsor Drake accepts fewer than twenty mandates annually, allowing him to remain directly involved from initial positioning through buyer strategy, negotiation, and final terms.

He leads the firm's fintech and payments practice, with coverage spanning payments infrastructure, cross-border payments and foreign exchange, wealth technology, digital assets, insurance technology, treasury, and office-of-the-CFO software. He also oversees the firm's work across B2B software, cybersecurity, and artificial intelligence.

Each mandate is supported by a dedicated execution team working directly under Jeff. Research, financial analysis, transaction materials, buyer engagement, diligence, and negotiation operate through a single senior chain of command. There are no layers between the Managing Director and the work.

Research & Published Work

Jeff directs Windsor Drake's research program: the published research library, published quarterly across fintech, AI, cybersecurity, and B2B SaaS. The program includes the firm's Insight Reports, the Market Intelligence deal and valuation database, the Fintech Exit Index, and the Acquirer Index. Every report is built on the same analytical infrastructure the firm applies to live sell-side engagements.

Working Papers

Selected Publications — Q2 2026

The complete library of 70 reports is maintained in the Windsor Drake research archive. Founder-focused analysis on valuation, earn-outs, diligence, and exit planning is published in Windsor Drake Insights, authored by Jeff.

Recognition

Windsor Drake research and Jeff's commentary are cited by the journalists and platforms covering technology M&A and the private markets.

Practice areas: sell-side M&A advisory · founder-led business exits · fintech and payments transactions · B2B SaaS · cybersecurity · AI software · business valuation · cross-border execution in the lower middle market.  Page updated August 2026.