Mergers and acquisitions are defining moments — the result of years of hard work, risk, and ambition. At Windsor Drake, we guide founders through these critical transitions with clarity, discretion, and high-touch execution.
We specialize exclusively in sell-side M&A for profitable, founder-led businesses across technology, digital, and traditional sectors. Whether you’re preparing for a full exit, exploring a recapitalization, or seeking a strategic partner, we lead the process from start to finish — ensuring you achieve the best possible outcome.
Windsor Drake is a modern boutique investment bank built for entrepreneurs. We run discreet, focused sale processes designed to maximize value and protect your legacy.
Founder-Centric – We work exclusively for business owners. No dual agency. No conflicts.
Tailored Strategy – Every process is unique, designed around your business and your goals.
Curated Buyers – We bring strategic acquirers, private equity firms, and family offices to the table — not time-wasters.
Discreet Execution – We protect your confidentiality at every stage of the transaction.
We advise founders on full or partial exits, managing every phase of the deal process:
Strategic positioning
Financial preparation
CIM creation and buyer outreach
Deal structuring, negotiation, and due diligence support
We help Canadian and U.S. business owners navigate international buyer interest, structuring deals with strategic or institutional acquirers across North America and abroad.
We leverage our relationships with top-tier private equity firms, family offices, and corporate acquirers to create competitive tension and secure favorable terms.
Not ready to sell today? We work with founders pre-transaction to position the business, clean up financials, and build toward a premium exit.
We focus on founder-led businesses with strong fundamentals across:
Technology – B2B SaaS, MSPs, IT services, vertical software
Digital – Ecommerce brands, agencies, platforms
Traditional – B2B services, industrials, trades, construction, distribution
Typical financial profile:
$1M–$20M in revenue
$500K+ in EBITDA
Privately held and founder-owned
We work with a limited number of founders each year to ensure high-touch execution and strong outcomes. If you’re considering a sale — now or in the future — we’d be glad to have a confidential conversation.
Sell-side M&A advisory for founders.
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