When I stepped into the Head of Product role at Healthpilot, we were in the middle of a big shift. We had just transitioned from a B2B2C model to a direct-to-consumer product. The platform had potential, but it was not working. Conversion rates were low, users were dropping off early, and no one was really sticking around.

The product felt heavy. The backend was complex and slow to move. Compliance restrictions made every change feel risky. There was no experimentation and very little learning. We needed a reset.

My first focus was simplifying how we worked. I partnered with engineering to clean up the architecture and unblock our delivery pipeline. At the same time, I worked closely with our compliance officer, government regulators, and our carrier partners to define new guardrails. That unlocked more flexibility than the team had ever had. We started running real experiments and finally had a way to learn from what users were doing.

We also went deep on research. I spent time listening to real users, interviewing seniors and caregivers, and watching where they got stuck. Most of them were confused or overwhelmed. They just wanted to know they were making the right decision, and they wanted to feel like someone had their back.

We rebuilt the product from the ground up. We focused on simplifying the UX, reducing friction, and helping people feel confident in the choices they were making. We added a guided questionnaire, redesigned the flow to match how people actually think about coverage, and layered in personalized recommendations using data from prescriptions and claims.

Over 2 years, we had created an enitrely different product. But more importantly, it started to actually work. It helped real people. We grew out conversion rates by 30x and provided over 125k personalized quotes in 2024. It became something we were proud of.