💻 Shawn Holmes

I%27m a working CTO with 30 years in technology and multiple production AI applications shipping at scale — not slide decks, not prototypes. At Wrapmate, I run the systems behind 10,000+ vehicles wrapped nationwide, a 5,000+ installer network across 50 states, and AI sales agents processing 1,000+ leads per day. I%27ve built and scaled real revenue-generating software, managed offshore and onshore engineering teams, and operated under SAFe and agile methodologies across enterprise and startup environments.

What makes me effective in an advisory or board role is that I%27m still in the trenches. I don%27t advise from theory — I advise from what I%27m shipping this quarter. I%27ve made the hard calls on architecture, hiring, vendor selection, and AI strategy with real money and real customers on the line. I bring that operational judgment, not just pattern-matching from a deck.

Companies that would benefit most:

- AI-first or AI-curious companies that need a board member who actually understands production ML/AI — what%27s real, what%27s hype, and what it takes to ship and maintain it.
- Marketplace or platform businesses scaling operations nationally — I%27ve navigated the logistics, trust, and automation challenges of a 50-state service network.
- Mid-market technology companies in growth or transformation mode that need pragmatic technology strategy, not enterprise bloat — someone who%27s built with constraints and knows when to buy vs. build.
- Companies where AI governance and architecture decisions are board-level concerns but the board lacks a practitioner%27s voice.