Windsor Drake
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Overview
10 - 49
Employees
2018
Year Founded
ABOUT WINDSOR DRAKE
Leading Sell-Side Tech M&A Advisory
Windsor Drake is a specialized M&A advisory firm that focuses on sell-side transactions for lower middle-market technology companies. We prioritize our clients by offering personalized, attentive service aimed at helping business owners maximize the value of their exits. Our team utilizes a strong network of strategic buyers and extensive expertise to provide customized solutions that lead to outstanding results. We recognize the specific challenges involved in selling a business and are dedicated to supporting our clients at every step of the journey, from valuation to completion. Windsor Drake is committed to maintaining the highest levels of integrity, professionalism, and results-oriented execution, making us a trusted ally for entrepreneurs looking to elevate their businesses. Our services include: Sell-Side M&A Advisory, Strategic Valuation and Positioning, Buyer Outreach and Negotiations, and Deal Structuring and Closing Support. Industries we serve include Technology, SaaS, and E-commerce. Allow Windsor Drake to help you realize the full potential of your business.
Languages Spoken
English
HIGHLIGHTS
10 - 49
Employees
2018
Year Founded
Services
Focus
Industries
Clients
Services Provided
69% Mergers & Acquisitions Consulting
16% Business Valuation Services
15% Business Consulting Services
About the Team
OUR STORY
Windsor Drake is a dedicated sell-side mergers and acquisitions advisory firm specializing in founder-led companies with $1M–$10M EBITDA and enterprise values between $3M–$50M. Operating from Toronto and New York, they expertly manage structured, competitive sales processes designed to maximize valuation, certainty, and alignment with sellers' goals primarily in fintech, cybersecurity, B2B SaaS, and AI software sectors. Their approach emphasizes senior professional involvement throughout, ensuring confidentiality and transparency. By systematically identifying and engaging a broad spectrum of qualified buyers—notably strategic acquirers, private equity firms, and family offices—they create competitive tension to secure superior transaction outcomes. Their tailored, research-backed methodology addresses the distinctive dynamics of technology-focused lower middle market M&A, delivering disciplined, high-standard advisory services with clear milestones and alignment to client success.