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Windsor Drake advises founders and owner-operators of lower middle market companies through every phase of a liquidity event: preparation, valuation, the sell-side transaction, and the diligence-through-close execution that protects net proceeds. Every engagement is led by a senior partner from initial meeting through close.
Core Service
Sell-Side M&A
Full-scope sell-side advisory from market positioning through close. Windsor Drake runs structured processes that put companies with $3M–$50M in enterprise value in front of 40–80 qualified buyers, creating competitive tension that drives valuations above what a single negotiation produces.
Diligence & Closing
Transaction Advisory
Quality of Earnings, financial due diligence support, deal structuring advisory, and integration planning. Transaction advisory protects net proceeds once the buyer’s team enters the room — defending normalizations, tightening working capital mechanics, and reducing retrades through close.
Pre-Transaction
Exit Planning
Most founders who sell underperform on valuation not because their business is weak, but because they started the process too late. Exit planning identifies the operational, financial, and structural changes that increase enterprise value 12–24 months before going to market.
Valuation
Business Valuation
Knowing what a business is worth requires more than a multiple applied to EBITDA. Windsor Drake conducts valuation analyses that account for revenue quality, customer concentration, recurring revenue mix, and sector-specific buyer appetite — the factors that actually move purchase price in a negotiated transaction.
The difference between an M&A advisor and a business broker is not the suit. It is the process.
A broker lists your company, waits for inbound interest, and negotiates a single offer. An institutional advisor builds a market for your business. That means identifying 200+ potential acquirers, running a structured outreach campaign, creating competitive tension between multiple bidders, and managing a process that gives you — not the buyer — control over timeline, terms, and information flow.
Windsor Drake operates at the institutional end of the lower middle market. The firm accepts fewer than 20 mandates per year and assigns senior advisory professionals to every engagement. There is no hand-off to junior staff after the pitch meeting. The person who structures the deal is the person who closes it.
For founders selling a business for the first time, this distinction matters more than it appears. The economics of a structured sell-side process versus a single-buyer negotiation often represent a 20–40% difference in total consideration — before accounting for deal structure, earnout terms, and post-close risk allocation.
Windsor Drake advises founder-led companies with enterprise values between $3M and $50M, typically generating $1M–$10M in EBITDA. The firm serves companies across several verticals, with particular depth in fintech, B2B SaaS, cybersecurity, business services, healthcare services, and home services.
The common thread is not industry. It is stage. Windsor Drake’s clients are founders who built real businesses — profitable, growing, defensible — and are now facing a decision about what comes next. Some are ready to sell outright. Others want a partial liquidity event with a private equity partner. Some are 18 months away and need to get the business ready first.
All of them share one characteristic: they have never done this before. That asymmetry — a founder negotiating against buyers who do acquisitions for a living — is exactly what an M&A advisory firm is designed to correct.
Every engagement begins with a confidential consultation. No obligation. No pitch deck. The conversation covers three things: what the business looks like today, what the founder wants from a transaction, and whether the timing makes sense.
If a founder is 12–24 months from being ready, Windsor Drake’s exit planning engagement identifies the specific changes that will increase enterprise value before going to market. Revenue concentration, customer contract structure, management team depth, financial reporting quality — these are the levers that move multiples, and they take time to fix.
If a founder is ready now, Windsor Drake moves directly into the sell-side process. That starts with a valuation analysis to establish the range of expected outcomes, followed by confidential marketing materials, targeted buyer outreach, and a structured process designed to generate multiple competing offers.
Once an LOI is signed and diligence begins, the dynamics shift. Buyers deploy financial and legal teams to validate — and often challenge — the seller’s assumptions. Windsor Drake’s transaction advisory capabilities cover Quality of Earnings preparation, due diligence support, deal structuring, and integration planning. The objective is to protect the economics negotiated during the sell-side process and maintain momentum through close.
The timeline from engagement letter to close typically runs 6–9 months for a prepared business. Less-prepared businesses benefit from the exit planning phase, which extends the total timeline but consistently produces better outcomes on price, structure, and terms.
Windsor Drake maintains dedicated coverage across six verticals. This is not a branding exercise. Sector knowledge determines which buyers get contacted, how the business is positioned, and what valuation benchmarks are relevant.
In fintech, the firm covers payments, regtech, wealthtech, insurtech, embedded finance, and lending platforms. Fintech acquirers evaluate businesses differently than generalist buyers — they care about API infrastructure, regulatory licensing, net revenue retention, and integration complexity. An advisor without fintech transaction experience will miss the positioning angles that drive premium outcomes in this sector.
The same principle applies across B2B SaaS, cybersecurity, business services, healthcare services, and home services. Each vertical has its own buyer ecosystem, its own valuation drivers, and its own diligence pressure points. Generalist advisors pattern-match across industries. Sector-focused advisors know which specific buyers are acquiring, what they are paying, and what deal structures they prefer.
Whether a transaction is six months away or two years out, the first step is the same. Windsor Drake offers a no-obligation consultation to assess where the business stands and what the realistic range of outcomes looks like.
All consultations are held under strict confidentiality.
Sell-side M&A advisory for founders.
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