Jack & Jill
Product Manager (+ Equity) at Ollyinsurance
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Job Title
Product Manager
Salary
Not Disclosed + Equity
Company Description
Ollyinsurance.com is a YC-backed London startup building an AI-native health insurer for the 57 million people in the UK, led by a founding team from Lemonade, AXA Health, and Oxford.
Job Description
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.
Location
London, UK
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.
Reasons to use Rodeo
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Grad scheme, placement, apprenticeship? Not sure what you want yet — that's fine. Your agent talks it through with you and turns "I have no idea" into a shortlist.
It searches the market for you
Every day your agent scans the market matching roles against what actually matters to you, not just keywords on a CV.
Only hits
No noise. No "maybe this fits." Just roles with a clear explanation of why they're right — and where to focus when applying.
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.
The ideal candidate
- 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.
Who are Jack & Jill?
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.
Get help with your application
Your very own career expert that helps elevate your application to the next level.
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.
How does this work?
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 it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
We never post fake jobs
This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.
Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.
We appreciate this can make them look a bit suspect, but there isn't much we can do about it.
Give Jack a spin!
You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.
“It took my CV and asked me questions relevant to understanding what kind of jobs to suggest for me. Suggestions were almost perfect. Jobs were exactly what I’ve been looking for.”
Jessica, London
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