Technology M&A Advisory | Strategic Sell-Side Representation for Canadian Tech Founders

Premium M&A Advisory for Mid-Market Tech Companies

Windsor Drake is a Canadian mergers and acquisitions advisory firm built for technology entrepreneurs seeking a high-value exit. Our platform is designed to provide founder-led, bootstrapped, and venture-backed tech companies with institutional-grade M&A execution, grounded in the methodology of leading global investment banks.

We act as sell-side advisors to founders who are ready to unlock equity value through a full or partial sale, recapitalization, or strategic merger. We combine deep domain knowledge in software, cloud infrastructure, IT services, and digital platforms with a bespoke approach tailored to the Canadian market.

Why Technology M&A Is Booming in Canada

The Canadian technology landscape has experienced explosive growth over the past decade, supported by a vibrant startup ecosystem, competitive engineering talent, and proximity to U.S. capital markets. Today, M&A has become the primary exit path for most mid-market technology companies.

Contributing factors to heightened deal activity include:

  • An increase in private equity buyouts and strategic consolidations
  • Public and private acquirers seeking IP, talent, and market share
  • Founders seeking liquidity amidst volatile public market conditions
  • U.S. and global buyers seeking Canadian innovation at favorable valuations
  • Cross-border tax optimization and capital deployment mandates

For more data on market activity and investment trends, visit Invest in Canada (https://www.investcanada.ca/) and the CVCA (https://www.cvca.ca/).

What Is Technology M&A?

Technology M&A involves the sale, partial sale, or merger of a tech-driven business to a financial or strategic acquirer. Windsor Drake focuses exclusively on sell-side mandates, representing business owners through the following models:

  • Full exits to strategic buyers or private equity
  • Majority recapitalizations with PE or family offices
  • Acquihire and IP-focused transactions
  • Cross-border mergers and tuck-in acquisitions

A professionally managed M&A process ensures founders retain control, maximize valuation, and avoid common pitfalls such as underpricing, limited competition, or misaligned buyer relationships.

Who We Advise

Our clients include:

  • B2B SaaS founders with $1M–$20M ARR
  • IT service providers with enterprise or government contracts
  • Cloud infrastructure and DevOps platforms
  • Industry-specific software (PropTech, HealthTech, FinTech)
  • Technology-enabled services (TaaS, managed services)

Typical profile:

  • $2M–$50M in revenue
  • $500K+ EBITDA or high gross margin growth model
  • Founder-led, bootstrapped or lightly capitalized
  • Clean financials, scalable infrastructure, and strategic differentiation

We support early-stage, growth-stage, and mature technology companies, whether seeking a strategic acquirer or financial partner.

Our Technology M&A Process

1. Initial Assessment & Strategic Fit

We begin with a confidential discussion of your company’s history, capital structure, intellectual property, financials, and future objectives. We help founders define their goals—full exit, partial sale, strategic alignment, or other outcomes.

2. Valuation Modeling & Go-to-Market Strategy

We develop a valuation model based on:

  • Forward revenue multiples for SaaS and software
  • Gross margin, CAC/LTV ratios, and retention metrics
  • Benchmarking against recent M&A transactions

We provide guidance on positioning your company in the market to attract a premium valuation, including narrative framing, competitive differentiation, and IP defensibility.

3. CIM and Data Room Preparation

We build a confidential marketing package (CIM) and financial data room to support buyer diligence. These documents include:

  • Product architecture and tech stack
  • Customer concentration and cohort data
  • Financial performance and forward projections
  • Capital structure and ownership
  • Founder and team profiles

4. Buyer Outreach

We run a structured outreach campaign to:

  • Strategic acquirers in Canada, the U.S., and globally
  • PE firms focused on software and tech-enabled services
  • Family offices and tech-focused investors

All outreach is confidential. Prospective buyers are vetted and required to sign NDAs before receiving sensitive information.

5. Term Sheet Negotiation & Due Diligence

We manage buyer interaction, negotiate Letters of Intent (LOIs), and lead diligence processes across:

  • Legal (IP ownership, customer contracts, employee agreements)
  • Financial (revenue recognition, deferred revenue, EBITDA normalization)
  • Technical (code base, security, data management)

6. Closing & Post-Transaction Support

We coordinate with legal, tax, and accounting professionals to finalize the transaction and support post-close integration, earnout monitoring, or transitional involvement.

Key Valuation Drivers for Technology Companies

Buyers evaluate a wide range of metrics when assessing a technology business. Key valuation levers include:

  • Recurring revenue (MRR/ARR)
  • Gross margin and CAC efficiency
  • Retention rates and churn analysis
  • Product scalability and codebase maturity
  • Founder/management continuity post-transaction
  • Contractual stickiness and expansion revenue (net dollar retention)

Typical valuation ranges (as of 2025):

  • B2B SaaS: 4x–12x ARR (depending on growth, retention, and margin)
  • IT Services: 6x–10x EBITDA
  • Tech-enabled services: 5x–8x EBITDA

Valuation can be influenced significantly by buyer competition, market tailwinds, and positioning.

Recent Canadian Technology M&A Transactions

  • Vertical SaaS (Construction Software)
    $7.2M ARR | 93% Gross Margin
    Sold to U.S. PE-backed platform consolidator
  • Cybersecurity MSP
    $12.5M Revenue | $2.8M EBITDA
    Acquired by a national strategic acquirer
  • Cloud Infrastructure Management Tool
    $3.6M ARR | High logo retention
    Sold to a global infrastructure software suite

These transactions reflect the increasing appetite for Canadian innovation in software, services, and vertical technology applications.

Why Windsor Drake?

Our firm brings the technical acumen of a Silicon Valley advisor with the strategic discipline of an institutional investment bank. We are not brokers—we are M&A professionals who operate with discretion, clarity, and focus.

  • Deep network of strategic and financial acquirers in tech
  • High-trust advisory model with senior-led execution
  • Sector-specific valuation and positioning expertise
  • Focused exclusively on sell-side mandates
  • Full-stack execution: strategy, marketing, negotiation, diligence

Founders choose Windsor Drake when the outcome matters. We work with clients who want thoughtful advisory, a highly curated process, and discretion from start to finish.

Legal and Tax Considerations in Technology M&A

Canadian technology founders must prepare for several legal and tax structuring decisions:

  • Share vs asset sale (and eligibility for LCGE)
  • Treatment of IP and software licenses
  • Rollover equity and cross-border repatriation
  • Employment and incentive arrangements
  • Earnouts, deferred consideration, and founder retention

We coordinate with leading legal counsel and tax advisors to ensure clean execution. We also offer introductions to M&A specialists in corporate law, tax planning, and IP law when needed.

See Canada Revenue Agency’s guide to business ownership transitions: https://www.canada.ca/en/revenue-agency/services/tax/businesses.html

FAQs

How long does the M&A process take?
6 to 9 months from kickoff to closing, depending on complexity and buyer diligence.

Do you work with pre-revenue startups?
Our focus is on revenue-generating companies. However, we selectively advise early-stage companies with IP, traction, or strategic interest.

What if I don’t want to sell 100% of my business?
Many clients opt for a partial sale or recapitalization, retaining equity and leadership while de-risking.

Do you run auctions or exclusive processes?
We design the right structure for your goals. For most mid-market tech companies, a limited, competitive process works best.

How do you charge?
We charge a modest retainer plus a success-based fee on close. All terms are disclosed transparently.

Begin the Conversation

If you own or operate a technology business in Canada and are exploring M&A—Windsor Drake provides the clarity, credibility, and discretion you need.

We help:

  • Maximize valuation and optionality
  • Manage buyer dynamics and negotiation
  • Avoid common founder pitfalls
  • Execute with precision and discipline

Windsor Drake | M&A Advisory for the Builders of Canadian Tech

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