Heel Toe Strategy Consulting · Toronto
We help founders, executives and boards think clearly about where to compete, what to build, and how to grow — and then turn that thinking into decisions people can act on.
The situations we are brought into
A growth plateau that could be a market problem, a product problem, or a focus problem. An AI opportunity everyone can see and no one can quite scope. A board that needs an independent view before a major bet. That's the work we do.
An experienced, independent voice in the room for the decisions with the longest shadows: major investments, leadership transitions, strategic transactions, and course corrections.
What does AI actually change for this business — its products, its costs, its defences? A grounded strategy, separated from the hype cycle, with a sequence to execute against.
Where should the company compete, and where should it stop? Market selection, positioning, portfolio focus, and the growth bets worth making — in that order.
Security is now a board topic, a sales topic and a product topic at once. We help leadership treat it as strategy — not just compliance — especially where AI is changing the threat and the opportunity.
Partnerships, acquisitions and investments evaluated on strategic fit first and spreadsheet second — including the honest case for walking away.
Strategy that survives contact with the calendar. Turning a decision into priorities, owners and measures — and cutting the initiatives that dilute all three.
Why Heel Toe
Large firms sell leverage: a partner sells, a team delivers. We work the other way. Every engagement is led directly by the principal — the person you meet is the person who does the work, sits in your meetings, and signs the recommendation.
That model isn't right for everything. It is right when the problem is judgement, not manpower: when you need someone who has sat on both sides of the table — operator, investor, board member — to help you see your own situation clearly.
The mark tells the same story: two pedals worked at once — one slowed on purpose, one blipped to keep momentum. It sits at the top of every page; the full story is on the About page.
How we work
Every engagement — a two-week assessment or a year-long advisory relationship — follows the same discipline. Read more about our approach →
Understand the real problem, in evidence — not the problem as first presented.
Frame the genuine options, price their trade-offs, and make a recommendation.
Turn the decision into a plan: priorities, sequence, owners, and measures.
Stay close enough to execution that the strategy survives reality — and adjust it when reality argues back.
“The value of an outside advisor isn't more information. It's a clearer decision — made sooner, with the trade-offs named out loud.”
That principle shapes every engagement we take. If we can't help you reach a clearer decision, we won't take the work.
Start a conversation
Bring the decision you're weighing — a market to enter, a product to bet on, an AI strategy to set, a board question to work through. You'll leave with a clearer frame for it, whether or not we work together.
The first step is a short, confidential conversation. No pitch, no obligation — just a direct discussion of the problem and whether we are the right people to help with it.