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Windsor Drake is a sell-side mergers and acquisitions advisory firm. We advise founder-led companies on the sale of their businesses, running structured competitive processes designed to maximize valuation, certainty of close, and alignment with the seller’s objectives.
Windsor Drake advises companies with $1M–$10M in EBITDA and $3M–$50M in enterprise value across four primary sectors: fintech, cybersecurity, B2B SaaS, and AI software. Offices in Toronto and New York.
Most founders sell a company once. The quality of the process—who runs it, how many buyers are engaged, how competitive tension is managed, how information is controlled—determines the outcome. That is the problem we solve.
We do not list businesses for sale. We run structured, time-certain sell-side M&A processes that systematically identify, qualify, and engage the full universe of relevant buyers—strategic acquirers, private equity firms, and family offices—and create the competitive conditions that produce superior transaction outcomes.
Every engagement follows a defined process with clear milestones, deliverables, and timelines. The methodology is consistent. The execution is tailored to the company, the sector, and the buyer landscape.
Preparation & Positioning
Financial analysis, market positioning, and creation of institutional-grade transaction materials—confidential information memorandum, management presentation, and financial model. The company is positioned the way buyers and investors evaluate acquisitions.
Buyer Identification & Outreach
Systematic mapping of the full buyer universe—strategic acquirers, private equity platforms, and financial sponsors with active mandates in the sector. Outreach is direct and senior-level, not mass-distributed.
Competitive Process Management
We control the timeline, the information flow, and the competitive dynamics. Multiple qualified parties are advanced through a structured process with defined bid rounds. Competitive tension is engineered through process design, not left to chance.
Negotiation & Close
LOI evaluation, definitive agreement negotiation, due diligence coordination, and transaction close. We evaluate offers across eight dimensions beyond headline price—including execution certainty, structural protections, and post-close alignment—to ensure the outcome reflects the seller’s full objectives.
Most advisory firms in the lower middle market rely on a limited network of buyer contacts. We rely on a systematic process that covers the full buyer universe for every engagement. The difference is measurable in both the number of qualified parties engaged and the competitive dynamics at the offer stage.
The senior professional who leads your engagement at the outset is the same person calling buyers, running negotiations, and managing the process through close. We do not hand engagements to junior teams after signing. Direct senior involvement at every stage is the standard, not the exception.
For each engagement, we build a buyer universe specific to the company’s sector, size, and strategic profile. This includes active strategic acquirers, private equity firms with relevant platform and add-on mandates, and qualified family offices. Buyer identification is research-driven, not limited to existing relationships.
Competitive tension is a product of process design. We control the timeline, the sequence of information disclosure, and the interaction between buyer parties to create the conditions under which acquirers submit their strongest terms. This is deliberate. It is not a function of luck or timing.
Confidentiality is maintained through strict information controls at every stage of the process. Company identity, financial details, and strategic intentions are disclosed only to qualified, vetted parties under executed non-disclosure agreements. No information is shared without the seller’s explicit written consent.
We concentrate advisory resources in sectors where we maintain active buyer relationships, publish proprietary valuation research, and have direct transaction experience. Sector depth allows us to position companies within the specific competitive and valuation context buyers use to evaluate acquisitions.
Fintech
Payments, wealthtech, insurtech, fraud and compliance software, cross-border infrastructure, treasury and AP/AR automation. Learn more →
Cybersecurity
Identity and access management, cloud security, endpoint and network security, DevSecOps, SIEM/SOAR, and AI-driven security platforms. Learn more →
B2B SaaS
Horizontal and vertical SaaS across healthcare, logistics, construction, proptech, manufacturing, and enterprise software. Learn more →
AI Software
AI infrastructure, MLOps platforms, workflow automation, AI-enabled healthcare, and AI-native cybersecurity applications.
We work with founder-led and privately held businesses in the lower middle market. Typical engagements involve companies with the following characteristics:
Confidentiality. Your employees, customers, competitors, and the broader market will not learn of your intentions through our process. All buyer engagement occurs under executed non-disclosure agreements. We do not list companies on any public marketplace, database, or platform. Disclosure is deliberate and controlled at every stage.
Transparency. From the first week through close, you will know what is happening, what comes next, and why. Every milestone, deliverable, and negotiation decision is communicated in advance. We do not operate behind closed doors.
Alignment. Our fee structure is weighted toward success. We earn the majority of our compensation when the transaction closes on terms that meet your objectives. Our incentive is to maximize your outcome, not to close any deal at any price.
Direct access. You will work directly with the senior professionals responsible for your engagement. Strategy, buyer dialogue, and negotiation are not delegated to junior teams.
Most founders sell a company once. The process determines the outcome. We exist to ensure that process is run at the highest standard.
The lower middle market—defined broadly as companies with $3M to $50M in enterprise value—is the most active segment of M&A by transaction volume and the most underserved by institutional-quality advisory. Founders in this segment frequently encounter advisors operating as business brokers: limited buyer outreach, no structured process, and minimal competitive tension. The result is a transaction negotiated bilaterally, where the buyer controls timing and terms.
A disciplined sell-side M&A process reverses this dynamic. When multiple qualified buyers are engaged simultaneously through a structured competitive framework, the seller retains control of the timeline, the information flow, and the negotiation leverage. The result is not just a higher valuation—it is a transaction with better structural protections, more favorable terms, and greater certainty of close.
Technology sectors—including fintech, cybersecurity, and B2B SaaS—trade on metrics and buyer dynamics that differ materially from broader M&A. Valuation in these sectors is driven by recurring revenue quality, net revenue retention, gross margin profiles, unit economics, and the defensibility of the company’s competitive position. An advisor without current sector intelligence cannot position a company effectively to the buyers who value these characteristics most.
Windsor Drake publishes quarterly valuation and M&A research across our coverage sectors. This research informs how we position every engagement: the comparable transactions, the operating benchmarks, and the buyer landscape are current, not drawn from generic databases or outdated references.
Windsor Drake operates from offices in Toronto and New York, advising on transactions across North America. Our cross-border positioning is particularly relevant for Canadian technology companies with U.S. buyer interest, a dynamic that is increasingly common in fintech, cybersecurity, and enterprise SaaS. We maintain active buyer relationships with acquirers and private equity firms in both markets.
Founders evaluating an exit readiness assessment or exploring the current M&A environment for their sector are welcome to begin a confidential conversation.
We advise companies with $1M–$10M in EBITDA and $3M–$50M in enterprise value. This places us in the lower middle market segment of M&A, where institutional-quality advisory is most needed and least available.
Our primary sectors are fintech, cybersecurity, B2B SaaS, and AI software. Within each, we cover specific subsectors where we maintain active buyer relationships and publish proprietary valuation research.
No. Windsor Drake is exclusively a sell-side advisory firm. We represent sellers only. This eliminates the conflicts of interest inherent in firms that advise both sides of transactions.
Our fee structure includes a monthly advisory retainer and a success fee payable at closing. The success fee is the primary component, aligning our compensation directly with the transaction outcome achieved for the seller.
A well-prepared sell-side process typically takes six to ten months from engagement to close. The timeline depends on the complexity of the business, the buyer landscape, and the pace of due diligence. We design each process with a defined timeline and clear milestones.
A confidential introductory conversation. We discuss your objectives, your company’s profile, and the current market context for your sector. There is no obligation, and the conversation is held under strict confidentiality. Contact us to begin.
The firm operates from offices in Toronto and New York, advising on transactions across North America with particular depth in cross-border M&A between Canada and the United States.
If your company meets the profile described above and you are evaluating a potential sale, we welcome a confidential introductory discussion. No obligation. No information is disclosed without your written consent.
All inquiries are held in strict confidence.
Sell-side M&A advisory for founders.
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