I've shipped consumer AI at Microsoft, helped lead a commerce startup to an exit with eBay, and built the AI program inside a national retailer. I've worked both sides of discovery — the platform deciding what customers see, and the brand fighting to be seen. I help leaders figure out which specific thing to do next.
I worked on the first version of Microsoft's Consumer Copilot, then built and co-led an enterprise AI program from scratch — governance, enablement, product strategy. I help you get past pilot theater to capability that survives both a board conversation and a legal review.
I taught Leader as Coach at eBay, developed product leaders for two decades, and spent years at a company built entirely around workplace culture. Coaching here is direct feedback from someone who's held the job, not a framework off a shelf.
I helped lead a commerce startup to an exit with eBay, built products inside a national retailer, and worked with early-stage companies at Madrona Venture Labs. Now I help brands navigate a harder question: how do you get found when AI assistants are the front door?
The Snoqualmie is my home river. Its three forks come together near where I live, and the country around them is where I run, ride, climb, and fish. It's terrain that rewards people who give it seasons, not visits.
Same with organizations. Most AI advice is either vendor enthusiasm or risk theater. Useful advice takes knowing your systems, your customers, and your constraints well enough to name the next move — and say what it will cost you.
I've been on both sides of that room: the operator accountable for shipping, and the advisor when the decision gets made. I taught mountaineering, climbing, and backcountry skiing before joining mountain rescue, and both taught the same thing — the party that reads conditions honestly is the one that comes home.
I've been both a product leader and a CTO. I can tell you whether the thing is worth building and whether it can actually be built.
You get named next steps and tradeoffs, not a maturity model.
Most AI programs fail on change management, not technology. That's where I spend the time.
The goal is your team's capability, not a retainer that never ends.
I helped lead a commerce startup to a successful exit with eBay and spent years there building marketplace and shopping products. I've since worked as a CTO as well as a product leader, which means I can go deep on architecture and feasibility, not just roadmap. Later I worked on the first version of Microsoft's Consumer Copilot — one of the earliest attempts to put a real assistant in front of a mass-market audience — and spent time at Madrona Venture Labs with companies at the earliest stage.
Most recently I led AI product strategy, governance, and enablement at REI, working directly with the C-suite on how a values-driven co-op adopts AI without compromising what it stands for. Coaching has run alongside all of it — I taught Leader as Coach at eBay, and my time at Limeade, a company built around employee wellbeing, taught me that technology strategy and culture strategy are the same conversation.
That path put me on both sides of the same problem: inside marketplaces and retailers that decide what gets surfaced, and alongside brands working to get surfaced — a problem changing fast now that AI assistants sit between customers and what they buy.
I work with a small number of clients at a time — private equity operating teams, commerce and retail leadership, and executives navigating the AI transition — as a fractional operator, advisor, and coach.
When I'm not working, I'm outside: trail running, biking, climbing, and fly fishing around the forks of the Snoqualmie — the river this firm is named for. That country taught me most of what I know about patience, conditions, and choosing routes. The rest I learned the hard way, in rooms where the decision actually mattered.
I take a small number of engagements at a time. If you're weighing an AI investment, a commerce shift, or your own next move, the first conversation is free and direct.
larry@middlefork.ai