As the founding PM at Ollyinsurance.com, you will define the strategy and UX for an AI health companion powered by Gemini and behaviour change science. You’ll bridge the gap between complex health data and empathetic, non-judgmental conversational experiences, directly impacting how millions of people manage their daily wellbeing and clinical care.
Product Manager at Ollyinsurance
Ollyinsurance.com is reimagining health insurance for the 57 million people in the UK currently without private coverage. As the founding Product Manager, you’ll lead the development of an AI-native 'invisible insurance' companion powered by Gemini and grounded in behavior change science. Backed by the YC ecosystem and led by veterans from companies like Lemonade and AXA Health, this is a rare opportunity to build a forgiving, empathetic health tool from the ground up. If you're passionate about AI UX and health data, join us in London to create a product people actually want to use every day and fundamentally change the insurance landscape.
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Location
London, United Kingdom
Compensation
Not Disclosed + Equity
Company
Ollyinsurance
Role overview
We are an AI-native private health insurance start-up building for the 88% of Brits without private cover.$3M pre-seed raised, PRA authorisation in progress, targeting March 2028 go-live. Backed by US institutional investors in the YC ecosystem.
What you will do
- Define the product strategy, vision, and roadmap for the Olly health companion across movement, sleep, mental health, and nutrition.
- Architect the LLM wrapper and conversational persona in partnership with engineering, ensuring empathetic and scientifically-grounded interactions.
- Drive member engagement and retention by designing proactive behaviors that celebrate small wins and meet users exactly where they are.
Who this is a fit for
- Proven track record shipping consumer-facing AI or LLM-powered products that achieved high daily active usage and meaningful user engagement.
- Deep expertise in behavior change science, including Motivational Interviewing or the COM-B model, ideally within a digital health or wellness context.
- Hands-on experience integrating health data from wearables like Apple Health or Google Fit to power personalized, data-driven product experiences.
Why this role is remarkable
- Lead the creation of a first-of-its-kind “invisible insurance” product that prioritizes a forgiving, empathetic AI health companion over traditional claims processing.
- Join a pre-launch startup backed by the YC ecosystem and built by an elite founding team from Lemonade, AXA Health, Cleo, and Oxford.
- Access a unique data advantage by combining real-time wearable data, NHS records, and clinical triage within a single generative AI context window.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
Jack’s an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack’s network.
If your profile’s a match and Ollyinsurance wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.