Our Philosophy
Built for
the founders journey.
Designed for the institutions shaping it, Waymark exists to help
entrepreneurship support organizations develop more capable
founders, and create clear evidence of the progress that follows.
WAYMARK /noun
A waymark is a marker along a route. It's a sign that shows where you are, how far you have come, and where to go next.
That idea shapes how we approach founder development.
We know who
we are building for.
Waymark works primarily with Black-led entrepreneurship support organizations developing Black and racialized founders across Canada.
We help strengthen founder development, measurement, and ecosystem positioning where generic programming or duplicated services are no longer enough.
We stay intentionally focused so every engagement receives thoughtful attention and design, making a clear connection to the outcomes your organization is trying to create.
Agency by design
We work closely with organizations that want programming and advisory shaped around their founders, mandate, and role in the ecosystem.
Experience That Informs the Work
Our Founder
Charles F. Milton founded Waymark after experiencing Canada’s entrepreneurship ecosystem from both sides: first as a founder building companies, raising capital, and navigating uncertainty—and later from inside the ecosystem supporting other entrepreneurs.
His background in data and analytics shapes how Waymark measures progress, surfaces useful insights, and helps organizations communicate stronger evidence of impact.
A three-time founder and former venture facilitator, Charles brings a decade of entrepreneurial and ecosystem experience to the work, including firsthand experience navigating the system as a Black entrepreneur.
Award-winning Globe & Mail Changemaker
and Black Tech Founder to Watch
Charles F. Milton
Founder & Principal
Waymark 1837
Ecosystem Experience
Better founders make better business.
If your organization is looking for a more deliberate approach to
founder development and ecosystem strategy, let's start with the challenge in front of you.
Waymark 1837 © 2026 . All rights reserved.
Waymark 1837 is the operating name of Waymark 1837 Insights & Advisory Group Limited.
Waymark 1837 is a consulting practice operating in Kjipuktuk in Mi’kma’ki, the ancestral and unceded territory of the Mi’kmaq, and works with organizations across what is now known as Canada. We recognize that our work and the economic opportunities it seeks to create benefit from the lands, relationships, and Treaties that make this work possible. We honour the Peace and Friendship Treaties and recognize our shared responsibilities as Treaty People.