Doug Milvaney — Product & AI Leader. Builder of things people actually use. Happiest when those things get people outside.

Hi, I'm Doug

I've spent 10+ years building AI-first products at Microsoft — Loop, Copilot Pages, Office — and I'm currently building Alpacalist, a packing app for people who do multiple activities on a single trip, because that's a problem I kept running into myself. I do this work because I believe technology should make it easier to spend time outside, not harder to escape it.

Passions

Product Strategy & Leadership

Figuring out what's worth building is the hardest part of product development. I build and grow high-performing, empowered teams who fall in love with the problems and don't get wed to a single solution.

Trails, Bikes & Skis

I've completed grueling gravel bike races (Rooted Vermont, The Ranger, Vermont Overland), rode my first Pan-Mass Challenge in 2026, and am halfway to becoming an Adirondack 46er. I also love finding ways to get outside with my young kids so they too can fall in love with nature and outdoor sports.

Climate & Sustainability

As a member of Protect Our Winters (POW) and 1% for the Planet, I've worked collaboratively to help increase the reach of the Outdoor State and research and choose impactful societal and climate action nonprofits to allocate donations to (such as StoveTeam International).

Career Highlights

Founded Alpacalist

Building a packing app for active travelers — designed around the reality that most trips involve multiple activities with different gear and packing needs, which generic list apps handle poorly. Started from a real frustration: I kept either overpacking or forgetting something critical on trips that mixed things like skiing, hiking, and biking. Now in invite-only beta.

Microsoft 365 Copilot App & Copilot Pages: AI Innovation

Lead product strategy and execution for core Microsoft 365 Copilot experiences, bringing model-forward, generative AI capabilities to millions of customers.

Product-Led Growth Initiatives

Defined and executed PLG strategy to drive awareness, adoption, and engagement of AI capabilities within Microsoft Loop. Leveraged in-product education, A/B experimentation, and GTM enablement.

Microsoft Loop: 0→1 Product Launch

Led early product conception, strategy development, and cross-functional execution for core pillars of Microsoft Loop—a new AI-first collaboration app.

Microsoft Office: Collaboration Experiences

Drove and delivered the asynchronous collaboration platform as part of Microsoft Office's reinvention of Word, Excel, and PowerPoint to unlock rich, customer-driven collaboration experiences.

Let's Connect

I'm a product leader who's spent a decade building AI and collaboration products at scale — and someone who'd rather work through a challenging problem out on the trail. I'm always happy to connect: whether you want to talk product, trails, or both.