Toronto · Ontario

Toronto M&A advisory for founder-led companies.

Windsor Drake is a Toronto-headquartered sell-side M&A advisory firm. We represent founders, families, and private-company shareholders across the Greater Toronto Area — and only their side of the table — pairing an institutional process with direct access to the U.S. buyers that drive premium outcomes for Canadian companies.

Toronto HQ · New York access · Sell-side only · Senior-led

Request a Confidential Discussion

The Firm

Headquartered in Toronto. Built to reach the buyers that matter.

Windsor Drake is a Toronto-headquartered sell-side M&A advisory firm representing founders, families, and private-company shareholders in structured, confidential sale processes. The Toronto office at 95 St Clair Avenue West anchors the firm’s Canadian practice.

A New York presence at 1270 Avenue of the Americas provides direct access to the U.S. private equity firms, strategic acquirers, and financial sponsors that make up the cross-border buyer universe behind premium outcomes for Canadian founders.

The firm advises on the sell side only, never buyers, eliminating the conflicts of dual-side representation. Every engagement is led by the managing director from first meeting through close, and the firm accepts a limited number of mandates each year so that senior attention is never diluted.

More than half of Canadian mid-market exits cross the border.

A Toronto advisor without active U.S. buyer relationships can run only half the process. Our Toronto and New York presence reaches both sides of the buyer universe directly, without intermediaries.

Cross-Border Buyer Access

Access to the buyers that acquire Toronto companies.

Toronto is home to Canada’s most active private equity firms, corporate acquirers, and family offices — but a large share of mid-market exits involve a U.S. or international buyer. The advisor who can access and manage that buyer set generates a materially different outcome than one limited to the domestic market.

Windsor Drake’s dual-city presence reaches the categories that acquire Canadian private companies: U.S. private equity running sector platform strategies, Canadian sponsors building domestic portfolios, strategic acquirers expanding into Canada, PE-backed platforms executing add-ons, and family offices and independent sponsors pursuing proprietary deal flow.

Each buyer universe is built specifically for the engagement, by strategic fit, acquisition history, sector focus, and capital capacity, then sequenced to produce multiple simultaneous offers at the LOI stage. That is where a seller’s leverage is greatest.

Sectors We Advise

Where we have buyer relationships and valuation depth.

Sector focus determines whether your advisor speaks the buyer’s language, understands what drives multiples in your vertical, and can position your business against the right comparable transactions.

B2B SaaS & Software

ARR quality, net revenue retention, cohort economics, and gross-margin dynamics, positioned for the premium SaaS-fluent buyers assign to recurring revenue. SaaS M&A

Fintech

Payments, lending, wealthtech, and regtech, where M&A demands fluency in regulatory frameworks and the specific universe of financial-institution and PE-backed buyers. Fintech M&A

Cybersecurity

Recurring revenue, retention, and compliance-driven demand, positioned for the PE platforms and strategics consolidating the sector. Cybersecurity M&A

Business Services

Professional services, staffing, facilities, and outsourced BPO, valued on contract quality, customer concentration, and revenue predictability. Business services M&A

Healthcare Services

Clinics, diagnostics, home health, and specialized care, an active consolidation theme where U.S. sponsors increasingly enter through Canadian platforms. Healthcare M&A

Home Services

HVAC, plumbing, electrical, and restoration with recurring revenue and route density, attractive to platform acquirers building regional scale across the GTA. Home services M&A

How the Process Works

A structured, five-phase sell-side process.

Designed to create competitive tension, control information flow, and maximize the founder’s net outcome, managed by senior professionals from the Toronto and New York offices.

Strategic assessment & exit readiness

A full review of financial performance, operations, customer dynamics, and positioning, plus a preliminary valuation and a candid discussion of objectives. We identify the value drivers that attract institutional buyers and the gaps to close before market through exit-readiness work.

Materials preparation

A blind teaser, a confidential information memorandum presenting the investment thesis, and a financial model with normalized, properly documented EBITDA, prepared to the standard institutional buyers expect.

Controlled market outreach

An engagement-specific buyer universe, contacted discreetly and under NDA. Identity is not disclosed until authorized, and the most qualified buyers receive materials on a timetable built to produce multiple simultaneous indications of interest.

Negotiation & letter of intent

We solicit, evaluate, and negotiate LOIs on the full economic structure, cash at close, earn-outs, working capital, reps and warranties, indemnities, and employment terms, not just headline price. Competitive tension at this stage is the seller’s single greatest source of leverage.

Diligence & closing

We manage due diligence across financial, legal, operational, and regulatory domains, and stay involved through the definitive agreement, working-capital true-up, and closing, including Canadian tax-structuring considerations that affect net proceeds.

Canadian Considerations

Tax and structuring for Toronto transactions.

Canadian transactions present structuring decisions that materially affect a founder’s net proceeds. An advisor who understands them negotiates from the outset, rather than discovering structural problems after the LOI is signed.

Share sale versus asset sale

A share sale can give the seller access to the Lifetime Capital Gains Exemption on qualifying Canadian-Controlled Private Corporation shares and capital-gains treatment; an asset sale does not qualify but may be preferred by buyers for liability and depreciation reasons. The optimal structure is deal-specific.

Cross-border considerations

U.S. buyers introduce Investment Canada Act review, potential national-security screening, Canada-U.S. tax-treaty provisions, withholding obligations, and foreign-exchange dynamics, the last of which has increased U.S. acquisitive interest in Canadian targets.

Corporate reorganization

Many founder-owned businesses benefit from pre-sale reorganization, crystallizing the exemption, purifying the corporation, or implementing a holding-company structure. These steps must be planned well in advance to be effective. We coordinate with your tax and legal advisors from the start.

Why Windsor Drake

What distinguishes the firm.

Sell-side only

The firm never advises buyers. When it sits across the table from an acquirer, there is no relationship to protect on the other side, and no reason to negotiate anything less than aggressively.

Senior-led execution

Every engagement is run by the managing director from mandate through close. The person who signs the engagement prepares the CIM, leads buyer calls, and negotiates the LOI. No bait-and-switch.

Selective model

A deliberately limited number of mandates each year ensures concentrated senior attention across a process that typically runs six to nine months, a depth high-volume firms cannot match on any one deal.

Cross-border buyer access

The Toronto-New York presence is not branding. It provides direct access to the U.S. PE firms and strategics that acquire Canadian mid-market companies, contacted directly, not through intermediaries.

Institutional-quality materials

CIMs, models, and valuation analyses prepared to the standard institutional buyers expect. Materials that meet a deal team’s analytical bar get read; materials that do not get deprioritized.

Sector specialization

Coverage concentrated in the verticals above, which keeps buyer relationships active and specific, rather than relying on a generic database that treats every industry the same.

Selling a Business in Toronto

Frequently asked questions

What does a sell-side M&A advisor do?

A sell-side M&A advisor manages the entire sale of a private company: valuation, institutional-quality marketing materials, identification and outreach to qualified buyers, management of competitive bidding, negotiation of the letter of intent and definitive agreement, and coordination of due diligence through closing. The advisor represents the seller exclusively and creates competitive tension among buyers to maximize the founder's outcome.

How is an M&A advisor different from a business broker in Toronto?

A business broker typically lists a company and waits for inbound interest, often working a local buyer pool on a volume model. A sell-side M&A advisor proactively builds the full universe of qualified buyers, including U.S. acquirers, runs a structured competitive process, and negotiates the full economic structure of the deal. For companies of meaningful scale, the difference in buyer coverage and leverage is significant.

How much does an M&A advisor cost?

Most M&A advisory firms charge a monthly retainer plus a success fee, typically a percentage of enterprise value that declines as deal size increases. The relevant measure is net outcome: advised, competitive processes consistently close at stronger multiples and on better terms than unrepresented sales.

How long does it take to sell a business in Toronto?

A typical sell-side process runs six to nine months from engagement to close, plus any pre-market exit-readiness preparation. Cross-border transactions involving U.S. buyers can extend timelines due to Investment Canada Act review and cross-border tax structuring.

Should I sell shares or assets?

It is one of the most consequential structuring decisions in a Canadian transaction. A share sale can allow access to the Lifetime Capital Gains Exemption on qualifying Canadian-Controlled Private Corporation shares and capital-gains treatment; an asset sale does not qualify but may be preferred by buyers for liability and depreciation reasons. The right structure depends on corporate organization, tax basis, buyer preferences, and the economics of the deal.

Can I sell my Canadian company to a U.S. buyer?

Yes. More than half of Canadian mid-market exits involve a U.S. or international acquirer. Cross-border sales add complexity, Investment Canada Act review, Canada-U.S. tax-treaty provisions, withholding, and foreign-exchange considerations. Windsor Drake's Toronto and New York presence provides direct access to U.S. buyers without intermediaries.

Will my employees or customers find out?

No. Confidentiality is maintained throughout. Your identity is not disclosed until you authorize release; all buyer contact begins with a blind teaser, and NDAs are executed before any confidential information is shared.

Will buyers expect me to stay on after the sale?

Often, yes. Many acquirers, particularly private equity, request a transition period of roughly six to eighteen months depending on your role and the depth of the management team. It is negotiated within the LOI and definitive agreement, alongside employment, non-compete, earn-out, and equity-rollover terms.

Offices

Toronto and New York.

TorontoHeadquarters

95 St Clair Avenue West
Toronto, ON

Tel 416.386.6608

New York

1270 Avenue of the Americas
New York, NY 10020

Tel 212.540.5013

Confidential Inquiry

Considering a sale in the Greater Toronto Area?

If you are a Toronto-based founder, family-business owner, or shareholder preparing for a transaction in the next 12 to 36 months, we conduct a confidential preliminary assessment of every inquiry, with no obligation.

Request a Confidential Discussion

All inquiries are strictly confidential. Toronto: 95 St Clair Avenue West · New York: 1270 Avenue of the Americas.