About

Built by Leaders. For Leaders.

Waypoint Collective was founded by two people who have spent their careers at the intersection of leadership, strategy, and the transformative power of place.

Compass and map — the tools of navigation and intention

Our Story

The Conviction Behind the Collective

Waypoint Collective was born from a simple but deeply held conviction: that the most consequential decisions of a leader's career are rarely made in a boardroom. They are made in the moments between — on a walk at dusk, over a long dinner, in the silence of a landscape that demands reflection.

Chris and Ruth Moore spent decades watching exceptional leaders struggle to find the space, the peers, and the perspective they needed to do their best thinking. The corporate retreat industry offered templates. The conference circuit offered noise. Neither offered what these leaders actually needed.

So they built it. Waypoint Collective is the result — a company designed from the ground up to create the conditions in which great leaders do their greatest work. Every experience we design, every cohort we curate, every destination we choose is in service of that single purpose.

We did not set out to build a travel company. We set out to build a thinking company that happens to travel.

The Founders

The People Behind the Collective

Contact

[email protected]

Chris Moore

Co-Founder & Managing Director

Chris Moore has spent over two decades advising C-suite executives and boards across North America and Europe. His career has taken him from the trading floors of Toronto to the boardrooms of Fortune 500 companies, and through it all, he has been fascinated by one question: what are the conditions that allow exceptional leaders to think exceptionally well?

That question led him to found Waypoint Collective. Chris brings to every program a deep understanding of the pressures facing senior leaders, a global network built over twenty years, and an instinct for the kind of environment that unlocks genuine strategic insight.

When he is not designing experiences, Chris can be found somewhere between the Canadian Rockies and the coast of Portugal — usually with his Macbook and a good bottle of wine.

Contact

[email protected]

Ruth E. Moore

Co-Founder & Chief journey Architect

Ruth E. Moore is the creative and operational force behind every Waypoint Collective experience. With a background spanning luxury hospitality, executive education, and organizational design, she brings a rare combination of aesthetic sensibility and operational rigour to the work of designing transformative experiences.

Ruth's philosophy is simple: every detail matters. The sequence of a meal. The light in a room at a particular hour. The precise mix of structured conversation and unstructured time. These are not incidental — they are the architecture of insight. Ruth designs them with the same care a great architect brings to a building.

Her work has taken her to private estates in Burgundy, innovation labs in Seoul, and expeditions to the Galápagos Islands. She brings all of it to bear on every program Waypoint Collective designs.

What We Stand For

Our Values

Intentionality

Nothing in a Waypoint experience happens by accident. Every element — from the venue to the fellow participants to the arc of the facilitation — is chosen with deliberate purpose.

Discretion

The conversations that happen in our programs are among the most candid our participants will ever have. We protect that candour absolutely. What happens in a Waypoint experience stays there.

Excellence

We hold ourselves to a standard that most of the industry does not attempt. Not because it is easy, but because our participants deserve nothing less.

Impact

We are not in the business of pleasant experiences. We are in the business of consequential ones. Every program we design is measured against the outcomes it produces.

Ready to Connect?

If you are curious about what a Waypoint Collective experience might look like for you or your team, we would welcome a conversation.

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