Mergers & Acquisitions

Sell-Side M&A Advisory for Founder-Led Businesses

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.

Our Approach

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.

How We Help

Sell-Side M&A

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

Cross-Border Transactions

We help Canadian and U.S. business owners navigate international buyer interest, structuring deals with strategic or institutional acquirers across North America and abroad.

Private Equity & Strategic Buyer Engagement

We leverage our relationships with top-tier private equity firms, family offices, and corporate acquirers to create competitive tension and secure favorable terms.

Pre-Sale Preparation

Not ready to sell today? We work with founders pre-transaction to position the business, clean up financials, and build toward a premium exit.

Sectors We Serve

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

Let’s Talk

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.