Exit Planning | Long-Term Preparation for Maximum Business Sale Value

What Is Exit Planning?

Exit planning is the structured process of preparing a privately held business—and its shareholders—for a future sale, transition, or recapitalization. It is not a transaction. It is a strategy.

At Windsor Drake, we work with Canadian business owners to help them plan 1 to 5 years in advance of an M&A event. Our goal is to position the company for maximum valuation, ensure personal and financial readiness for shareholders, and design a transaction that reflects years of preparation—not weeks of reaction.

Why Exit Planning Matters

Most businesses are unprepared for the rigors of a competitive sale process. Financials may be inconsistent. Contracts may be informal. Key personnel may be undocumented. Growth stories may be unproven. The result is value left on the table—or deals that never close.

Exit planning eliminates these risks. It allows you to:

  • Understand and influence your valuation years in advance
  • Correct structural issues that reduce deal certainty
  • Prepare your team, clients, and operations for transition
  • Make personal financial and estate plans with clarity

We help founders move from business owner to asset manager—with control, leverage, and foresight.

Who Needs Exit Planning?

Exit planning is ideal for:

  • Founders planning to sell in the next 1–5 years
  • Family business owners with no clear succession plan
  • Entrepreneurial teams preparing for their first exit
  • Shareholders who’ve received unsolicited interest from buyers
  • Private equity portfolio companies within 24 months of hold maturity

Our clients range from $5M–$200M in revenue and operate across sectors including business services, industrials, HVAC, software, logistics, construction, and more.

The Windsor Drake Exit Planning Framework

Our exit planning engagements are structured and phased. Every plan is customized, but the framework remains constant.

Phase 1: Shareholder Alignment & Goal Setting

We begin by understanding the personal, financial, and professional goals of each stakeholder. Clarity at this stage ensures decisions stay grounded through the entire exit lifecycle.

Deliverables:

  • Exit readiness assessment
  • Shareholder liquidity objectives
  • Target timeline and flexibility range
  • Post-exit financial lifestyle planning

Phase 2: Valuation & Market Benchmarking

We perform a market-based business valuation using comparable transactions, sector-specific multiples, and normalized EBITDA analysis.

Deliverables:

  • Preliminary valuation range
  • Key valuation levers and risks
  • Buyer perception analysis
  • Competitive positioning vs. peers

Phase 3: Financial & Operational Optimization

This is the value-building stage. We help strengthen financial presentation, contract structure, pricing models, organizational alignment, and operational resilience.

Focus areas:

  • Revenue quality (recurring vs project-based)
  • Gross margin improvement
  • Contract terms, pricing stability, churn reduction
  • Management structure and documentation
  • Working capital and cash flow visibility

Phase 4: Diligence Preparation

We build a preliminary data room and begin organizing key documents, financials, HR materials, and compliance records in a diligence-ready format.

Deliverables:

  • Diligence checklist and data templates
  • Governance and shareholder documentation review
  • Clean-up of loose contracts and reporting gaps
  • Risk mitigation plan for buyer red flags

Phase 5: Strategic Process Planning

Once your business is structurally exit-ready, we work with you to design the optimal path to market—timing, buyer universe, transaction type, and process strategy.

This may include:

  • Auction vs. targeted process decision
  • Buy-side pre-marketing / interest gauging
  • Confidential outreach protocols
  • Selection of legal and accounting teams

Our Role as Exit Planning Advisors

Unlike brokers or tax accountants, Windsor Drake is an integrated exit planning advisor. We understand what buyers want—and we know how to shape a business so it commands premium terms.

We work alongside your existing team, including:

  • Accountants and controllers
  • Legal counsel and corporate governance advisors
  • Estate planners and wealth advisors
  • Tax consultants and family office leadership

Our role is to lead the business preparation process, structure the roadmap, and ensure your company is ready—when the market is ready.

The Cost of Poor Planning

Failure to plan leads to:

  • Lower sale price due to risk adjustments
  • Limited buyer interest due to financial gaps
  • Increased earnouts or delayed payments
  • Last-minute legal and tax surprises
  • Team disruption and client churn during process

Exit planning reduces these risks and gives sellers control over timing, valuation, and structure.

FAQs

Do I need to sell soon to start exit planning?
No. The earlier the better. Many of our best outcomes came from clients who started preparing 2–3 years in advance.

What if I don’t know when I want to sell?
That’s fine. Exit planning helps create readiness, even if the exact date is uncertain.

Will buyers know I’m planning to sell?
No. All work is done confidentially, with no external outreach unless authorized.

How long does an exit plan take to complete?
We typically work with clients over 6–18 months, depending on goals and company complexity.

Do I need to change my legal or accounting firm?
Not at all. We collaborate with your current advisors and enhance their ability to support you.

Begin Exit Planning with Confidence

If you’re a Canadian business owner considering a sale in the next 1 to 5 years, Windsor Drake provides the expertise, structure, and strategy to ensure your exit is not just successful—but exceptional.

We help:

  • Maximize valuation through proactive improvements
  • Eliminate red flags and increase buyer competition
  • Align ownership, legal, tax, and personal goals

Windsor Drake | Exit Planning for Canada’s Business Owners

Book a Strategy Session