Strategic Advisory | High-Impact Strategic Guidance for Canadian Business Owners

What Is Strategic Advisory?

Strategic advisory is more than transactional consulting. It is long-term, high-trust partnership built to help business owners, boards, and shareholders make complex decisions involving growth, capital, succession, exit, and strategic repositioning. At Windsor Drake, we serve as strategic advisors to privately held Canadian companies operating in sectors where precision, timing, and clarity matter.

Our strategic advisory practice is designed to help clients navigate inflection points—whether preparing for a future sale, responding to inbound acquisition interest, evaluating capital markets opportunities, or planning internal transitions.

This is not about slide decks or financial engineering. This is about long-term alignment, decision readiness, and execution planning.

Our Philosophy: Clarity, Confidentiality, Execution

Our advisory model is grounded in the ethos of institutional investment banking but adapted to serve the needs of privately held companies in Canada. We work directly with owners, entrepreneurs, family offices, and private equity stakeholders to define, plan, and execute on the most important decisions they will make.

We do not offer outsourced strategy consulting. We work with clients when decisions matter—when outcomes are significant, when timing is critical, and when alignment must be built across multiple stakeholders.

Who We Advise

Windsor Drake provides strategic advisory services to:

Founders or families planning a business exit within 12–36 months
Owners evaluating unsolicited offers from buyers or investors
Companies considering recapitalization, succession, or dividend recap
Private equity portfolio companies approaching hold maturity
Family offices managing complex intergenerational ownership structures
Businesses in transition due to partner exits, market shifts, or leadership change

We work across sectors where clarity and planning are essential to long-term value creation, including:

Business services
Industrial and manufacturing
HVAC and infrastructure services
Software and tech-enabled services
Logistics and supply chain

Why Strategic Advisory Matters

Most companies are unprepared for the decisions they will eventually need to make. Strategic advisory helps owners think proactively, rather than reactively. The best exits, partnerships, and capital events are years in the making—not weeks.

Advisory work helps business owners:

Understand their valuation and market positioning
Prepare for buyer expectations and due diligence
Evaluate unsolicited inquiries with clarity and leverage
Reduce business risk and increase attractiveness to investors
Build organizational readiness for sale or succession

Our role is to turn a potential opportunity into an actionable path forward.

Our Strategic Advisory Offerings

1. Exit Planning & Pre-Market Readiness

We work with clients 1–3 years before they go to market, helping them align goals, normalize financials, strengthen operational leverage, and prepare for premium valuations.

Key services:

Preliminary market valuation and benchmarking
KPI improvement planning (margin, contract structure, client mix)
Financial statement cleanup and preparation
Buyer perception analysis
Go-to-market strategy planning

2. Inbound Buyer Readiness & Response

Many of our clients are approached directly by strategic or private equity buyers. We help you respond—not react—with structure, control, and leverage.

Our process includes:

NDA review and response protocols
Buyer qualification and motivation analysis
Rapid internal valuation review
Deal structure modeling and term sheet review
Option creation: how to respond with confidence and alternatives

3. Board & Shareholder Advisory

We support multi-partner businesses and investor-owned firms by providing guidance on shareholder alignment, capital deployment, and transaction strategy.

Ownership restructuring
Divestiture planning
Capital raise feasibility
Governance and fiduciary preparation

4. Corporate Development & Capital Strategy

For growing companies, we assist in evaluating partnerships, M&A growth, or strategic capital alignment without rushing to market.

Market mapping and partner identification
Strategic acquisition target identification
Joint venture and alliance modeling
Capital stack optimization

How We Work

Strategic advisory mandates are structured as either:

Retained Advisory Engagements: Monthly or quarterly retainers for ongoing access and planning
Project-Based Engagements: Defined deliverables, such as market readiness reports, transaction preparation plans, or buyer response playbooks

We engage with a maximum number of advisory clients at a time to ensure depth and focus. All conversations are confidential. All mandates are senior-led.

Why Windsor Drake?

M&A Expertise: We know what buyers want, how they think, and how deals are done. We prepare you accordingly.
Market Insight: We operate across Canada and are deeply familiar with capital markets, private equity mandates, and strategic acquirer trends.
Execution Focus: We advise to action. We don’t just deliver reports—we help you make confident, well-informed moves.
Trusted Relationship: Our clients view us as extensions of their executive team. We earn that trust over time.

Frequently Asked Questions

Do I need to be ready to sell to work with Windsor Drake?
No. Many of our advisory clients are 1–3 years away from a potential sale. We help them plan now to maximize future options.

I’ve been approached by a buyer. Should I hire an advisor?
Yes. Without a qualified advisor, you risk underselling, under-negotiating, or reacting under pressure. We help you assess and respond with clarity.

How long do engagements last?
Strategic advisory engagements can range from 3 months to 24+ months depending on the scope and nature of your business.

Do you advise outside of Canada?
We focus on Canadian companies but frequently advise on inbound international interest and cross-border scenarios.

Do you advise on capital raising?
Selectively. While we do not raise capital, we provide strategic input on capital structure planning, investor screening, and readiness.

Start a Strategic Conversation

If you are a Canadian business owner facing a high-stakes decision or considering a future sale, Windsor Drake offers high-trust, high-caliber strategic advisory grounded in real-world execution.

We help you:

Gain clarity on value and options
Build leverage and deal readiness
Execute strategic decisions with discipline

Windsor Drake | Strategic Advisory for Canada’s Business Leaders