Toronto M&A Advisory | Strategic Sell-Side M&A Services for Canadian Business Owners
Elite M&A Advisory for Founders and Private Companies in Toronto
Windsor Drake is a Toronto-based mergers and acquisitions advisory firm providing institutional-grade sell-side representation to business owners across Canada. We specialize in helping founders, families, and private equity portfolio companies plan and execute premium-value exits with precision, discretion, and competitive tension.
Our firm operates with the discipline of a top-tier investment bank, offering full-process M&A advisory designed specifically for private middle-market companies. From valuation to negotiation, Windsor Drake delivers a senior-led, outcomes-driven experience tailored to the complexity of your business and the standards of global buyers.
Why Toronto Is Canada’s M&A Epicenter
As Canada’s financial capital, Toronto is home to the country’s most active buyer and investor ecosystem. The city hosts the headquarters of major private equity firms, corporate acquirers, law firms, and family offices. It is also the top region in Canada for outbound and inbound M&A activity.
Founders operating in or near the Greater Toronto Area (GTA) benefit from immediate access to:
Strategic buyers seeking industry consolidation
Private equity groups actively deploying capital into Canadian businesses
Advisory professionals with deep transactional experience
Cross-border and U.S.-based acquirers looking to enter or expand in the Canadian market
According to data from PitchBook and Mergermarket, Toronto accounts for over 60% of Canada’s mid-market M&A volume.
What Is Sell-Side M&A Advisory?
Sell-side M&A advisory is a structured, confidential process designed to position, market, negotiate, and close the sale of a business. For founders and shareholders, it is a one-time opportunity to extract maximum value—financially and personally—from the enterprise they’ve built.
Windsor Drake’s sell-side M&A services include:
Strategic exit planning
Formal market valuation
Preparation of all go-to-market materials
Discreet outreach to targeted buyers
Negotiation of deal terms and structure
Coordination of diligence and closing
We act as your lead advisor from beginning to end, managing the transaction while you continue to operate and grow your company.
Who We Advise
We represent companies based in Toronto and across Canada, typically with:
$10M–$200M in annual revenue
$2M–$25M in normalized EBITDA
Clear market leadership, differentiation, or scale
Recurring or contract-based revenue models
Clean corporate structures and growth potential
We specialize in M&A advisory for:
Business services and facility services firms
Construction, trades, and industrial contractors
HVAC, fire protection, and building systems operators
Technology and software companies (especially B2B SaaS)
Distribution, logistics, and value-added fulfillment
Manufacturing and engineered product businesses
Windsor Drake’s M&A Process
1. Exit Planning & Shareholder Strategy
We begin with a confidential strategy session to align on:
Timing and readiness to sell
Owner involvement and post-close goals
Key valuation drivers and risks
Tax optimization, legal structure, and wealth planning (in partnership with your advisors)
This ensures that all parties understand the road ahead and that the deal strategy reflects real-world business dynamics and personal priorities.
2. Market Valuation & Preparation
We conduct a valuation based on:
Comparable private and public market transactions
Sector-specific EBITDA multiples and buyer trends
Business performance, customer profile, and growth trajectory
Our team prepares a full suite of marketing and diligence materials, including:
Confidential Information Memorandum (CIM)
Normalized financial model with EBITDA adjustments
Dataroom and documentation structure
Preliminary diligence checklist and buyer-facing summaries
3. Buyer Outreach & Qualification
We run a targeted, NDA-protected outreach campaign to:
Strategic buyers (industry peers, consolidators, international firms)
Private equity firms with experience in your sector
Family offices and independent sponsors with operational alignment
All outreach is discreet, and your identity is not disclosed until you authorize release. Our buyer pool includes hundreds of pre-qualified groups active in Canada and the U.S.
4. Term Sheet Negotiation
We create competitive tension by managing multiple interested buyers through:
Initial calls and management meetings
Simultaneous LOI (Letter of Intent) solicitation
Valuation comparison and term structuring
We negotiate on:
Purchase price and consideration structure (cash, earnout, rollover)
Working capital target and net debt adjustments
Employment or consulting arrangements post-close
Tax efficiency and legal structuring (asset vs. share sale)
5. Diligence, Closing & Transition
Our team manages diligence across financial, legal, operational, and regulatory domains. We coordinate with your legal and accounting advisors to:
Organize contracts, employee data, customer documentation
Prepare for legal review and Q&A workflows
Manage exclusivity timelines and negotiation pacing
Ensure a clean close with minimal disruption to the business
We stay involved through closing and post-transaction transition support, including earnout planning and integration.
Key Valuation Drivers in Toronto M&A
Buyers of private Canadian companies assess value based on:
Normalized EBITDA and historical margin consistency
Recurring revenue, backlog, or contract base
Customer concentration and retention
Team strength and management depth
Growth trajectory and capital expenditure profile
Working capital and cash flow conversion
Toronto-based companies often receive a premium due to:
Proximity to major buyers and capital markets
Access to talent, infrastructure, and deal professionals
Demand from cross-border and international acquirers
Why Windsor Drake
Sector-Specific Expertise: We understand the operating and financial dynamics of the industries we serve.
Elite Buyer Access: We maintain deep relationships with strategic and financial buyers across North America.
Full-Process Execution: We lead from strategy through close, managing every detail with precision.
Alignment & Discretion: We act exclusively for sellers—never both sides—and operate confidentially throughout the process.
Institutional Standards: Our materials, models, and negotiations meet the expectations of sophisticated buyers and capital partners.
Legal and Tax Considerations
Selling a Canadian business involves:
Asset vs. share transaction planning
CRA tax strategy, LCGE use, and capital gains deferral
Employment law and subcontractor classification
Lease, customer, and vendor contract assignment
Real estate and IP transfer or licensing
We coordinate closely with your legal, tax, and wealth advisors—or introduce experienced M&A professionals where needed. For CRA resources, visit: https://www.canada.ca/en/revenue-agency/services/tax/businesses.html
FAQs
Can I retain a portion of the business post-sale?
Yes. Many deals involve a partial sale with retained equity or rollover into the new entity.
Do buyers need me to stay on?
Often yes—typically 6–18 months depending on your role and team depth.
How long does the M&A process take?
On average, 6–9 months from engagement to closing.
Will my team or customers find out?
No. We maintain strict confidentiality and only disclose as authorized.
Do I need audited financials?
Not required. Reviewed financials are often sufficient when normalized properly.
Begin the Conversation
If you are a Toronto-based founder, family business, or shareholder preparing for a sale in the next 12–36 months, Windsor Drake offers strategic advisory and full-process execution to deliver exceptional outcomes.
We help:
Maximize valuation through competitive positioning
Run institutional, buyer-driven M&A processes
Protect your legacy while creating long-term financial results
Windsor Drake | Toronto’s Sell-Side M&A Advisory Firm for Privately Held Companies