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"?
In driving, heel-and-toe is a technique for changing down smoothly at speed — braking and blipping the throttle at the same time, so the car stays balanced through the corner and comes out faster.
It's a fair description of strategy work at an inflection point. Companies rarely get to stop to change direction. They have to slow one thing down and speed another up, simultaneously, without losing balance — a market exited while a product is launched, costs cut while growth is funded, today's business protected while tomorrow's is built.
That balancing act — deliberate, practised, and done at speed — is the work this practice exists to do. It is also, literally, our mark: the two pedals of the technique, 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 the technique itself: two pedals, worked at the same time. The tall pedal is the brake — judgement, restraint, the thing slowed down on purpose. The gold pedal, tipped forward, is the throttle — the blip that keeps momentum alive while everything changes gear. Slow one thing down. Speed another up. Never lose balance.
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.