Medical Director (+ Equity) at Ollyinsurance

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Job Title Medical Director

Salary Not Disclosed + Equity

Company Description Ollyinsurance.com is a $3M pre-seed digital health insurer founded by veterans from Lemonade and AXA Health, building the UK's first AI-native health coverage platform. Backed by the YC ecosystem, they are designing an invisible insurance experience that makes private coverage accessible to the 88% of the UK population currently without health insurance.

Job Description As the founding Medical Director at Ollyinsurance.com, you will serve as the clinical backbone of a groundbreaking AI-native insurer. You will own clinical governance, shape automated triage architecture, and lead the path to MHRA Class IIa classification. This high-impact role blends deep medical expertise with hands-on product building in a pre-launch environment.

Location London, UK

Why this role is remarkable

• Founding-level clinical hire at a $3M pre-seed startup, working directly with founders from Lemonade and AXA Health to redefine health insurance.
• Lead the clinical logic for the UK's first AI-native health insurer, pursuing complex MHRA Class IIa medical device classification for automated triage.
• Massive market opportunity targeting the 88% of the UK population currently underserved by traditional insurers with a modular, consumer-first health product.

What You Will Do

• Own clinical governance frameworks, safety screening protocols, and sign-off on AI-assisted clinical decision trees to ensure MHRA-grade compliance.
• Partner with product and engineering teams to translate complex medical pathways into structured, scalable logic for the AI-native triage architecture.
• Define the clinical strategy for human-in-the-loop automation while managing relationships with clinical advisors, panel partners, and regulatory bodies like the PRA.

The ideal candidate

• GMC-registered physician with a license to practice, ideally with a clinical background in general practice, urgent care, or digital primary care.
• Proven experience in clinical governance, patient safety, or regulatory compliance, specifically with MHRA medical device regulation or CE/UKCA marking.
• A builder mindset with a genuine interest in AI and health technology, comfortable navigating the ambiguity of a founding-stage, pre-launch startup environment.

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.

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.

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