Kevin Cannon

Background

About Kevin Cannon

I'm a cross-functional systems thinker who happens to have deep ML engineering experience and a finance background. After nearly five years building AI and ML systems at Thirty Madison — a telehealth company spanning multiple brands and care models — I'm making a deliberate move into product management.The pivot isn't about leaving technical work behind. It's about stepping into the part of the problem I've always been drawn to: understanding what people actually need, figuring out whether the conditions exist to solve it, and making sure the solution is legible to everyone it needs to reach.A few things the career record shows that don't fit neatly on a resume:I have a strong feasibility instinct. I've repeatedly identified the constraint that would sink a project before the team hit it — and I've been right often enough that it's a pattern, not luck. In product contexts, knowing when not to build is as valuable as knowing how.I'm a translator by disposition. Making complex quantitative work legible to non-specialists — not as a communication task, but as a design instinct — is something I've done throughout my career without being asked to. It shows up in how I build tools, structure outputs, and explain tradeoffs.I've done PM work without the title. At Thirty Madison I served as both PM and sole ML engineer on multiple projects — running discovery, managing stakeholder roadmaps, and making prioritization calls with no dedicated product support.Currently building a career management platform in stealth — a structured system for helping people surface, articulate, and leverage their full professional capabilities. It's the most direct expression of what I actually care about — and yes, I'm dogfooding it.