Toronto Investment Bank | Strategic Advisory for Mid-Market M&A and Capital Transactions

Institutional-Grade Investment Banking Services in Toronto

Windsor Drake is a Toronto-based investment banking and M&A advisory firm providing sell-side representation, strategic advisory, and capital transaction services to mid-market private companies. Our team combines global investment banking standards with hands-on execution to deliver exceptional results for founders, families, and private equity sponsors.

We specialize in complex M&A transactions, recapitalizations, and exit strategies for businesses generating $10 million to $200 million in annual revenue. With deep experience across industrials, technology, healthcare, and B2B services, we serve as a trusted advisor to Canada’s most ambitious privately held companies.

Why Toronto Is Canada’s Investment Banking Capital

Toronto is home to Canada’s financial core—including its most active private equity funds, family offices, commercial lenders, and corporate acquirers. The Toronto region accounts for over 60% of Canada’s middle-market M&A activity, and hosts the country’s most competitive buyer landscape.

A Toronto-based investment bank offers unparalleled access to:

  • Capital markets infrastructure

  • Legal, tax, and diligence support firms

  • Global acquirers and cross-border buyers

  • Deep relationships across institutional capital providers

This proximity to capital and talent enables Windsor Drake to structure and execute transactions that maximize value and minimize risk.

Our Core Investment Banking Services

Sell-Side M&A Advisory

We act as the exclusive sell-side advisor for private company shareholders preparing for a sale. Our mandate includes:

  • Exit strategy and valuation planning

  • Preparation of CIM and financial materials

  • Buyer outreach and relationship management

  • Term sheet negotiation and structure optimization

  • Coordination of due diligence and legal review

We manage competitive, confidential processes designed to unlock strategic value for our clients.

Strategic Advisory

For companies evaluating options ahead of a sale, Windsor Drake offers:

  • Exit readiness analysis

  • Business valuation and benchmarking

  • Capital structure and shareholder alignment strategy

  • Buy-side target identification (for growth-by-acquisition)

We help business owners make informed, strategic decisions well before they go to market.

Recapitalizations and Partial Exits

We advise on equity recapitalizations that allow owners to:

  • Take partial liquidity while continuing to grow the business

  • Transition family ownership without selling to competitors

  • Bring in growth capital or strategic minority partners

Our capital markets experience ensures alignment of incentives between buyers, sellers, and investors.

Debt and Growth Capital Advisory

We help growth-stage or asset-heavy businesses source:

  • Senior and subordinated debt

  • Growth equity and minority investment

  • Family office or private capital partnership

Windsor Drake evaluates optimal funding structures, then runs a capital raising process to source and secure non-dilutive, strategic capital.

Who We Serve

Windsor Drake represents privately held Canadian companies with:

  • $10M–$200M in revenue

  • $2M–$25M in EBITDA

  • Strong operating performance and growth potential

We advise businesses across:

  • Business services and B2B platforms

  • Software and technology (especially SaaS)

  • Industrial and construction services

  • Healthcare services and life sciences

  • Manufacturing, engineering, and distribution

Our clients are often founder-led, family-owned, or private equity sponsored companies preparing for generational transition or institutional sale.

Windsor Drake’s Toronto Investment Banking Process

1. Discovery & Strategic Positioning

We begin with a confidential discovery phase to:

  • Assess business performance and shareholder goals

  • Evaluate timing and market positioning

  • Normalize financials and identify valuation drivers

We develop a roadmap tailored to the client’s objectives.

2. Market Preparation

Our team prepares investment-grade materials, including:

  • Confidential Information Memorandum (CIM)

  • Adjusted financial model

  • Dataroom and diligence planning

  • Buyer/investor target list (strategics, PE, family offices)

3. Controlled Outreach & Buyer Engagement

We conduct a discreet outreach process to:

  • Qualified acquirers and capital providers

  • Pre-screened parties under NDA

  • Toronto-based and cross-border buyers

Outreach is fully managed and controlled to protect confidentiality.

4. Term Sheet & Deal Structuring

We lead negotiation of Letters of Intent (LOIs), focusing on:

  • Valuation and structure (cash, rollover, earnout)

  • Working capital targets and net debt

  • Tax efficiency and legal structuring

  • Employment/consulting terms post-close

We maintain leverage through competition and manage all term sheet dynamics.

5. Due Diligence & Close

We coordinate all diligence workflows:

  • Legal, financial, operational, and HR review

  • Buyer requests, Q&A, and dataroom control

  • Legal documentation and funds flow

Our role is to protect client interests through every stage of the transaction.

Why Windsor Drake

  • Toronto-Based: Embedded in Canada’s capital markets and buyer ecosystem

  • Sell-Side Specialists: 100% focused on advising sellers—not both sides

  • Industry Depth: Deep sector expertise across industrials, tech, and services

  • Senior-Led Execution: No handoffs. Our senior advisors manage your deal start to finish

  • Institutional Quality: CIMs, models, negotiations built to global IB standards

Legal & Tax Considerations in Canadian Transactions

We coordinate with your legal and accounting advisors to navigate:

  • Asset vs. share deal structuring

  • Capital gains exemption and CRA compliance

  • Employment law and subcontractor treatment

  • Lease and real estate transfers

We can also introduce trusted transaction law firms and tax specialists if needed. More info: https://www.canada.ca/en/revenue-agency/services/tax/businesses.html

FAQs

Do you raise capital as well as sell businesses?
Yes. We provide growth capital advisory for debt and minority equity.

Do you work with U.S. buyers?
Yes. Over 50% of our buyers are cross-border or international.

Can you keep my company confidential during the process?
Yes. We only disclose to qualified, NDA-signed parties approved by you.

How long does the process take?
6 to 9 months, depending on deal complexity.

Begin the Conversation

If you are a Toronto-based business owner or shareholder considering a sale, recapitalization, or capital raise, Windsor Drake offers elite-level advisory tailored to Canada’s mid-market.

We help:

  • Maximize value through structured, competitive processes

  • Connect you to strategic buyers, investors, and capital partners

  • Execute with discretion, precision, and alignment

Windsor Drake | Toronto’s Investment Bank for Privately Held Companies

Book a Private Strategy Call