Michael Gross

WORK HISTORY

EDUCATION

SKILLS

ABOUT MICHAEL GROSS

I\'ve spent 30 years turning IT organizations around. Five times, different companies, different problems — the pattern is always the same: a team that\'s lost credibility with the business, delivery that\'s fallen behind, and leadership that needs to see a different future before they\'ll invest in one.AI is the sixth turnaround. And it\'s the most powerful tool I\'ve ever had.Right now I\'m Director of IT at Outdoor Cap Company, where I\'m doing something most IT leaders are still talking about: converting a traditional development team into an AI engineering group. Not adding AI tools. Restructuring how the team thinks, builds, and delivers — with AI as the foundation, not the feature. We went from dabbling to running multiple Claude sessions simultaneously in about three months. The target is 3x productivity by Q4 2026. We\'re on track.But I\'m not just doing this at work.In March 2026 I launched Coffee Tokens — an AI education brand built entirely in public, on a zero-dollar budget, using the same free and low-cost tools I teach about. Every framework, workflow, and lesson comes from real implementation, not theory. If it doesn\'t work at 5AM on a Tuesday before my workday starts, I don\'t teach it.That\'s the positioning no one else has: military background, serial turnaround leadership, hands-on AI transformation, and building in public — at the same time, in the same season of life.If you\'re an IT leader trying to figure out how to make AI real inside your organization — not a pilot, not a proof of concept, but a genuine culture shift — that\'s the conversation I\'m interested in.Follow along at Coffee Tokens. The build is live.