Founder bio
The operator behind the product.
Background
My career has been built one rung below the C-suite — as an engineer, then a manager, then a leader whose consistent work has been developing the Managers, Directors, and VPs around me. That mentorship — helping senior operators move into the roles they were built for, then grow through them — is the through-line and the domain knowledge WaypointCareer is built on.
The product extends that practice upward. Where 1:1 mentorship reaches one person at a time, AI scales the same craft into evaluations, playbooks, and decision-support tuned for the levels above mine. I’m interviewing CIOs, CTOs, and COOs as the platform evolves, so the executive-tier surfaces land in their reality and not in my assumptions.
Why I built WaypointCareer
The product started where these usually do — with a frustration. I’d been laid off, deep in a job search, watching rejections arrive faster than I could process them. The standard advice was the usual menu: hire a coach, upgrade LinkedIn Premium, get a recruiter on the phone. All of it expensive, episodic, and dependent on someone else being engaged when I needed them.
What I actually needed didn’t exist. A system I could run on my own, every day, that made small consistent moves compound — readiness calibrated against the next level, a network that didn’t decay between searches, a brand built over months instead of improvised on a deadline. A career run as a practice, not a panic.
So I built it. WaypointCareer is the flywheel I wish I’d had two years before I needed it.
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Try the product
The shortest way to understand what I built is to use it.