Nov 11, 2025
Welcoming Donna Boyer to Team Cowboy!

We’re thrilled our longtime Cowboy collaborator and friend Donna Boyer has joined as a Venture Partner on our investment team.
Donna brings an awesome and rare mix of product leadership experience to work with startups. She’s built and led both consumer and enterprise teams, worked in ad tech, marketplaces, healthcare and more - and led product teams from the earliest stages to public company scale.
Her career includes product leadership roles at:
- WeightWatchers, where she led Product, Design, Engineering, Clinical, and Operations—expanding the company’s GLP-1 offerings and launching their Menopause program.
- Teladoc Health, where – as Chief Product Officer – she expanded primary care, mental health, and pediatrics, and integrated chronic condition management to enable whole-person care
- Airbnb, where she was the first Head of Product for Hosts & Homes, launched Airbnb Plus, and led the company’s anti-discrimination initiatives
- StitchFix, where she built the company’s first Product team, accelerating growth through the introduction of business models, product lines and international expansion
- RMG Networks, where she served as GM and Head of Product, creating in-store digital experiences for brands like Starbucks and The New York Times (we worked together here, ramping product & revenue, raising a $20m series B, then weathering the great financial crisis)
- Yahoo, where she led network personalization—building the first system to tailor content across properties and evolve the company’s ad targeting models
- She began her career at Harvard Business School, researching the impact of technology disruption on legacy industries.
Donna will spend her time on:
- Finding & evaluating early stage healthcare-focused ventures
- Supporting Cowboy-backed teams on post-investment product strategy and execution
Healthcare - why now?
Many health-focused startups have faced headwinds in recent years. So adding a dedicated talent to help us find and back health-oriented innovators might seem a bit contrarian.
Yet the potential to improve healthcare outcomes remains enormous. We see this window as a great time to back founders who will be grounded by the hard lessons learned, and we still see the opportunity to provide meaningful value to consumers or enterprises in a multi-trillion-dollar industry in need.
In the age of AI, world class product vision, velocity and execution is more important than ever for teams to get right. Donna’s perspective, empathy for customers and teams, and deep operational experience make her an incredible resource for founders in the Cowboy community.
Please join us in welcoming Donna - she can be reached at Hello@cowboy.vc or Donna@cowboy.vc!
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