SELL-SIDE M&A ADVISORY

Most founders sell their company once. The outcome depends entirely on the process.
Windsor Drake represents founder-led companies in sell-side transactions engineered to maximize valuation, compress timelines, and control outcomes. Fewer than 20 mandates per year. Every engagement partner-led from first meeting to close.
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MANDATES PER YEAR

$3M–$50M

CLIENT REVENUE RANGE

100%

SENIOR-LED EXECUTION

2

OFFICES IN NORTH AMERICA
THE FIRM

Institutional execution for founder-led companies

Windsor Drake was built for a specific gap in the market: founders of $3M–$50M revenue businesses who deserve the same caliber of sell-side execution that a $500M company receives — but from advisors who understand the dynamics of founder-owned businesses.

The firm limits mandates to ensure that every engagement receives full partner attention. Each process is structured to create competitive tension among a curated group of 10–15 qualified acquirers, compressing timelines while maximizing leverage at every stage of negotiation.

No junior staffing. No mass-market outreach. No passive listings. Windsor Drake runs controlled, confidential processes for founders who treat their exit as the most consequential financial decision they will make.

ADVISORY SERVICES

Three ways Windsor Drake serves founders

Sell-Side M&A

Full representation in company sales. Windsor Drake manages the entire process — positioning, buyer identification, outreach, competitive tension, negotiation, and close — so founders stay focused on operating the business through transaction.
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Exit Readiness

For founders 12–24 months from a potential sale. Windsor Drake identifies the operational, financial, and strategic adjustments that directly impact valuation — then works alongside management to execute them before going to market.
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Strategic Advisory

Majority recapitalizations, partial exits, and capital raises for founders who want liquidity without full exit. These structures allow founders to de-risk personal wealth while retaining operational control and upside in the next phase of growth.
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HOW WINDSOR DRAKE OPERATES

A process built for control, speed, and maximum value

01

Alignment

Define the founder’s financial, strategic, and personal objectives. Map the ideal buyer profile. Set the terms of engagement before a single outreach is made.

02

Positioning

Construct the investment narrative and materials that frame the business as the most compelling acquisition in its sector. This determines how buyers perceive value from first contact.

03

Controlled Outreach

Engage 10–15 hand-selected acquirers — each vetted for capacity, strategic fit, and track record. These are direct relationships, not cold introductions. Confidentiality is absolute.

04

Execution & Close

Drive competitive tension through a structured multi-party process. Manage diligence, documentation, and negotiations to institutional standards. Compress timelines. Close with certainty.
SELECT ENGAGEMENTS

Outcomes driven by process discipline

B2B SAAS

Vertical SaaS platform serving North American logistics operators

Sale to strategic acquirer. Process completed in under 5 months with multiple competing offers at close.
WINDSOR DRAKE — EXCLUSIVE SELL-SIDE ADVISOR
FINANCIAL TECHNOLOGY

Payments infrastructure provider with recurring revenue across SMB clients

Structured process with financial and strategic buyers. Achieved valuation above initial ownership expectations.
WINDSOR DRAKE — EXCLUSIVE SELL-SIDE ADVISOR
TECHNOLOGY-ENABLED SERVICES

Digital-first business services company with multi-year client contracts

Cross-border transaction involving Canadian and U.S. counterparties. Founder retained equity upside post-close.
WINDSOR DRAKE — EXCLUSIVE SELL-SIDE ADVISOR
INDUSTRY FOCUS

Sector depth where it matters

B2B SaaS

Vertical and horizontal SaaS businesses with $3M–$50M in recurring revenue. Windsor Drake understands the metrics buyers prioritize: net revenue retention, CAC payback, and gross margin structure.
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Financial Technology

Payments, lending infrastructure, insurance technology, and regulatory technology. The firm advises fintech companies where buyer interest spans both strategic acquirers and growth-focused financial sponsors.
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Cybersecurity

Identity, endpoint, compliance, and managed security businesses. Consolidation activity in this sector remains elevated, creating favorable conditions for sellers with defensible technology and sticky revenue.
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Business Services

Staffing, consulting, professional services, and technology-enabled outsourcing. PE buyer activity in business services remains among the highest of any sector, driven by recurring revenue models and margin expansion opportunities.
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Healthcare Services

Non-clinical healthcare services including revenue cycle management, health IT, behavioral health platforms, and care coordination. Regulatory tailwinds and demographic shifts continue to drive consolidation and premium valuations.
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Home Services

Residential services including HVAC, plumbing, electrical, pest control, and landscaping. Platform acquirers and private equity roll-up strategies have made this one of the most active sectors in lower middle market M&A.
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STANDARDS

What Windsor Drake guarantees on every mandate

The firm operates at institutional standards regardless of deal size. The same rigor applied to a $500M transaction governs a $15M engagement.

Absolute Confidentiality

Employees, customers, and competitors will not learn of a potential transaction unless the founder authorizes disclosure. Zero confidentiality breaches to date.

Partner-Led at Every Stage

The partner who leads the first conversation leads every negotiation, every buyer call, and the closing table. No handoffs. No delegation to junior staff.

Full Process Transparency

From the first week to close, founders know exactly what happens next, when, and why. Every milestone documented. Every decision explained. No ambiguity.

Controlled Timelines

Windsor Drake processes are measured in months, not years. Structured milestones, defined deadlines, and active management of buyer momentum ensure transactions close on schedule.
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Evaluating a potential transaction?

Windsor Drake accepts a limited number of new mandates each quarter. All inquiries are confidential and carry no obligation.

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windsor drake b2b saas investment bank

Sell-side M&A advisory for founder-led middle market companies.

 

Services
Our Firm
Offices
95 St Clair Ave E
Toronto, ON
1270 Avenue of the Americas
New York, NY 10020

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