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The Cowboy Team

Donna Boyer

Executive-in-Residence (EIR)

Donna brings hands-on experience leading product teams through every stage of growth. She loves partnering with founders who turn bold ideas into products that make everyday life work better, and she is especially passionate about using data, AI, and behavioral design to reshape health and wellness.

Before joining Cowboy as an EIR, Donna served as Chief Product Officer at WeightWatchers and at Teladoc Health, helping both companies evolve toward more integrated, engaging consumer experiences while expanding their clinical offerings. Earlier, she held product executive roles at Stitch Fix, Airbnb and early-stage startups (where she first met Aileen way back when!)

Donna earned her degree in Economics from Swarthmore College and began her career at Harvard Business School researching emerging technologies and creative destruction. She lives in San Francisco and outside of work can be found hiking Bay Area trails, playing board games, or riding roller coasters.

What’s something you collect or are weirdly particular about?

I own multiple label makers—from a cute pink one I saw on Instagram to an industrial-strength model from a garage sale. My house is filled with of clear boxes with labels ranging from Mac chargers to gummy candies. It’s deeply satisfying and somewhat concerning.

What’s a superpower outside of work?

My family is uncannily good at escape rooms. We’ve got a mix of learning differences and neurodiversity that make us a spiky, unstoppable team, like the X-men

Favorite comfort food?

Popcorn. The stress level of my week is directly correlated to the amount of popcorn debris on my floor.

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