Leading an early stage health startup to product market fit in 2 years
Empowering people to live happier, healthier lives
Founded in 2014, League set out to modernize an antiquated—and often broken—health system. What began as a mission to make care more accessible and equitable quickly evolved into Health OS™, a white-label platform that helps businesses improve workforce health by connecting improvements to overall wellbeing of employees to the lowering of premiums businesses pay to insurers.
I led the company’s 0→1 journey, shaping the design and product strategy that defined the core experience and carried it from concept to a live, scalable product. Those foundations now power a fully integrated, personalized healthcare platform serving more than 20 million people across North America and Europe.
Notable outcomes
$72M USD raised from Seed to Series B
By 2018, cumulative ARR had grown 430% and average deal sizes were 17× larger than the year before.
7x NPS score over industry average
Earned a score of 79 while I was lead and the company was simultaneously named to KPMG’s 2018 Fintech 100 and Deloitte’s Fast 50.
70% MoM app engagement
A steady 4.7+ star rating in the App Store, backed by more than 5,000 reviews.
For every $1 invested in preventative care, it saves a person $5.60 long-term
That single insight sparked a string of deep dives, interviews, and experiments that ultimately reshaped our direction. Instead of aiming to be a more customer-centric insurance broker, we expanded into a white-label health platform—one built with licensed practitioners and designed to offer rich education, seamless access to care, and reward systems that aligned with real health journeys.
This shift enabled the platform to surface truly relevant next-best actions for every individual, boosting engagement, satisfaction, and our ability to influence meaningful health outcomes.
Today, League’s core differentiator still stems from that evolution: delivering personalized healthcare engagement within an ecosystem that mirrors the full continuum of care.
❝
This app has completely changed my experience with my health insurance and my overall focus on health for the better. Love it!!
A League member
Personalized health for employees, data-backed ROI for employers
By the end of our first year, we’d hit $3M in ARR—clear proof we were onto something. With that traction, we pivoted toward employers, positioning HR leaders and CPOs as our primary buyers.
To keep pace in year two, I scaled the design team from two to five, adding product designers and UX researchers across onboarding, core product, and a brand-new employer experience team. Our mandate was simple but demanding: validate ideas fast across a diverse mix of buyers, end-users, and licensed health practitioners—and quickly discard anything that couldn’t sustain or scale.
What ultimately took hold was a tightly integrated health data platform that revealed the collective health of a company’s workforce and demonstrated how League could help drive down insurance premiums as employee wellbeing improved. Layer in insurance brokering, personalized onboarding, and a full-featured mobile app—complete with an early chatbot, pre-LLM era—and we built a platform flexible enough to serve businesses of any size.
A pursuit worth scaling, a legacy to be proud of
The foundation of what League is today was largely laid in year two. As the company moved upmarket, it expanded rapidly—adding more than 40 insurance carriers and introducing an in-house health concierge—all in the months leading up to its $47M Series B raise.
By then, I had already moved on from League, proud of the work and team I helped build and the patented Health OS™ ecosystem that evolved from those early design decisions.
A decade later, League’s continued growth is proof that an economically sustainable model can thrive in an industry long structured around profiting from illness rather than preventing it.
