About
An independent practice, built around one idea: senior judgement, applied directly.
Heel Toe Strategy Consulting is a boutique strategy and advisory practice based in Toronto, working with companies across North America.
Why "Heel Toe"?
Heel toe is the shape of a single step. Your heel lands, your toe pushes off — that's one step, and it's how every walk and every run is built. Nobody gets anywhere in a leap. They get there one step at a time, at whatever pace the ground allows.
It's a fair description of how companies actually change. Not in one dramatic bound, but step by step — each step deliberate, balanced, and pointed at where you're going. Walk when the terrain demands care. Run when it opens up. Either way, the mechanics don't change: heel, toe, next step.
That rhythm — steady, grounded, always moving — is the work this practice exists to do. And it's our mark: one step, heel and toe, drawn at the top of every page of this site.
The practice
Heel Toe is deliberately small. We take a limited number of engagements at a time, work directly with founders, executives and boards, and stay independent of any vendor, product or platform. Our focus is the places where strategy, artificial intelligence and security now intersect, and where the cost of a muddled decision is highest.
Clients engage us when the question is consequential, cross-functional, and short on honest outside perspective: a direction to set, a bet to size, a board to convince, a course to correct.
The mark
Our mark is a single step. The long shape is the heel, planted — grounded, deliberate, the weight committed. The gold shape, tipped forward, is the toe pushing off — momentum, the next step already beginning. Heel, toe. One step at a time, whether you walk or run.
At a glance
- Independent and principal-led
- Based in Toronto; clients across North America
- Focus: AI and security strategy
- Audiences: founders, executives and boards
- Formats: assessments, projects, ongoing advisory
What we don't do
Honesty about fit matters as much as capability.
- We don't sell implementation, software or staff augmentation
- We don't take engagements where the decision is already made and only validation is wanted
- We don't work on volume — a small number of clients, done properly
How the practice is led
Principal-led, by design
Every Heel Toe engagement is led directly by the firm's principal — an advisor with senior, first-hand experience of decisions like these. There are no hand-offs and no junior delivery teams: the person in the first conversation is the person who does the work and stands behind the recommendation. Client relationships are confidential, and engagements are accepted selectively, a small number at a time. Principal details shared on introduction.
Start a conversation
A good first conversation costs nothing but an hour.
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 fit to help with it.