Property Services M&A Advisory | Strategic Sell-Side Representation for Canadian Facility & Property Services Companies

Institutional-Grade M&A for Canada’s Property Services Sector

Windsor Drake is a Canadian M&A advisory firm delivering sell-side representation for mid-market property services companies. We advise founders, families, and private equity owners on strategic exits, recapitalizations, and divestitures. Our process is modeled on the execution standards of top-tier investment banks and tailored specifically for Canada’s commercial and residential property services market.

From building maintenance and HVAC servicing to janitorial, landscaping, fire protection, and facility management, Windsor Drake runs confidential, competitive M&A processes that position property service providers for premium outcomes.

Why Property Services M&A Is Accelerating in Canada

The Canadian property services industry is undergoing a sustained period of consolidation. Market fragmentation, coupled with rising demand for integrated facility solutions and outsourced services, has attracted strategic and financial buyers alike.

Key drivers of deal flow include:

  • Private equity firms rolling up route-based, recurring revenue service businesses

  • Strategic acquirers expanding footprint, capability, or vertical specialization

  • Cross-border buyers entering Canada for platform acquisition

  • Aging founders and ownership succession across service-based SMBs

With buildings aging, ESG standards tightening, and outsourcing increasing, property services businesses with loyal clients, recurring revenue, and well-trained field teams are in high demand.

For industry data and trends, refer to Statistics Canada (https://www.statcan.gc.ca/) and Canadian Facility Management & Design (https://www.reminetwork.com/).

What Is Property Services M&A?

Property services M&A refers to the sale, merger, or recapitalization of companies delivering outsourced services to commercial, industrial, multi-residential, or institutional buildings. These include:

  • Building maintenance & facility management

  • Janitorial and custodial services

  • HVAC, fire protection, and mechanical maintenance

  • Landscaping and snow removal

  • Security, monitoring, and access control

  • Elevator, pest control, and environmental health services

Transactions often involve:

  • Share or asset sales to strategic buyers or sponsor-backed platforms

  • Recapitalizations with equity rollover for continued growth

  • Carve-outs of specific divisions or geographic territories

  • Succession-driven transitions with founder exit

M&A in this space requires domain knowledge of:

  • Contract-based recurring revenue

  • Seasonal workforce and subcontractor dynamics

  • Client tenure and renewal cycles

  • Pricing mechanisms, route density, and technician utilization

Who We Advise

Windsor Drake advises Canadian companies across:

  • Commercial janitorial & cleaning services

  • HVAC and building systems maintenance

  • Fire protection and life safety systems

  • Grounds maintenance and snow clearing

  • Full-service facility management providers

Typical client profile:

  • $5M–$150M in annual revenue

  • $1M–$15M in adjusted EBITDA

  • 50–500+ field employees (W-2 or subcontracted)

  • Multi-year commercial or institutional contracts

  • Strong local or regional brand presence

Our Sell-Side M&A Process for Property Services Firms

1. Confidential Strategy Review & Valuation Assessment

We begin with a private consultation to align on ownership goals and assess the business’s operational and financial readiness for market.

We evaluate:

  • Contract backlog and renewal history

  • Revenue seasonality and customer retention

  • Normalized EBITDA margins and labor costs

  • Geographic and vertical concentration

This informs a valuation range, potential transaction structures, and buyer targets.

2. Market Positioning & Go-to-Market Material Development

Our team prepares a professional, confidential marketing package to position the business for sophisticated buyers.

Includes:

  • CIM (Confidential Information Memorandum) detailing service lines, clients, team, and financials

  • Normalized financial model with labor metrics and margin by service type

  • Dataroom preparation with legal, HR, financial, and contract documents

We frame your business as a scalable, compliance-ready platform with defensible cash flow and operational infrastructure.

3. Controlled Buyer Outreach & NDA Process

We discreetly contact a curated list of pre-vetted acquirers:

  • Private equity firms active in property and facility services

  • Strategic consolidators seeking growth through acquisition

  • National and cross-border buyers targeting Canadian platforms

  • Infrastructure funds with yield mandates and ESG overlays

All outreach is conducted under NDA, and no information is shared without client approval.

4. Negotiation, Term Sheet & Structure Management

We coordinate multiple LOIs (Letters of Intent), driving competition and extracting optimal deal terms.

We negotiate on:

  • Enterprise value and equity consideration

  • Earnouts, seller notes, and working capital peg

  • Employment, transition, and equity rollover terms

  • Tax structuring and asset vs share transaction decisions

Windsor Drake protects seller leverage and ensures clarity across economic and legal components of the deal.

5. Diligence & Closing

We manage the diligence process from buyer data requests to final contract execution.

Diligence areas include:

  • Labor structure (W-2, T4A, union, independent)

  • Client contracts and renewal/termination clauses

  • Insurance, risk, and WSIB status

  • Equipment ownership, leases, and supplier agreements

  • Payroll, HR, and safety compliance (including COR, ISO)

We coordinate closely with your legal, tax, and accounting teams to ensure a smooth close.

Key Valuation Drivers in Property Services M&A

Buyers assess value based on:

  • Recurring vs project-based revenue mix

  • Client diversity, longevity, and contract renewal rates

  • Labor efficiency, field tech utilization, and margin structure

  • Seasonality management and route optimization

  • Safety compliance and industry certifications

Typical multiples:

  • 4.5x–6.5x EBITDA for general janitorial and grounds maintenance

  • 6x–8x EBITDA for HVAC and technical service contractors

  • 7x–10x EBITDA for multi-vertical or compliance-driven facility managers

Premiums are paid for:

  • Long-term institutional or government contracts

  • Regional density with scalable ops

  • Strong second-tier management teams

  • Documented processes, tech stack, and ESG alignment

Market Trends

  • PE roll-ups expanding in HVAC, fire protection, and janitorial services

  • Cross-border acquirers targeting platforms in Ontario, Alberta, and Quebec

  • ESG mandates increasing buyer interest in green-certified vendors

  • End users outsourcing non-core building operations more aggressively

Windsor Drake monitors buyer mandates, valuation comps, and strategic shifts across the North American property services sector.

Why Windsor Drake

  • Deep Industry Insight: We understand route-based labor models, seasonal margin structures, and property manager relationships

  • Elite Buyer Access: Our network includes private equity, corporate buyers, and infrastructure funds targeting this sector

  • Discreet, Senior-Led Process: No business listings. No public marketing. Controlled and confidential from start to close

  • Seller-Only Representation: We represent sellers—never both sides. Our interests are fully aligned with yours

Legal, Tax & Regulatory Considerations

Property services M&A often involves:

  • Asset vs share sale analysis

  • CRA tax planning, LCGE eligibility, and rollover structuring

  • Employment law compliance (particularly for union shops)

  • Subcontractor misclassification and WSIB review

  • Contract assignability, bonding, and insurance audits

We work with your existing advisors or refer M&A-competent tax, legal, and accounting professionals to support you.

See CRA’s resources: https://www.canada.ca/en/revenue-agency/services/tax/businesses.html

FAQs

Can I stay on part-time after the sale?
Yes. Many founders stay on in transitional or consulting roles for 6–24 months.

Can I sell part of the company and keep equity?
Yes. Partial recapitalizations with equity rollover are common.

Will my employees be affected?
We structure transitions to preserve continuity and protect team culture.

Do buyers prefer asset or share deals?
It depends on tax and legal considerations. We model both and help optimize the outcome.

How long does a deal take?
6 to 9 months on average from engagement to closing.

Begin the Conversation

If you own or operate a property services company in Canada and are considering a sale, recapitalization, or succession plan, Windsor Drake offers the experience, process control, and buyer access to deliver a premium M&A outcome.

We help:

  • Structure and execute a competitive, confidential sale process

  • Position your company to attract top-tier buyers

  • Preserve your legacy and maximize financial outcomes

Windsor Drake | M&A Advisory for Canada’s Property Services Sector

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