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Medical Director at Ollyinsurance

Are you a physician who thinks like a builder? A YC-backed startup is hiring a founding Medical Director to serve as the clinical backbone of the UK’s first AI-native digital health insurer. You will own clinical governance, shape AI architecture, and lead MHRA medical device classification. This isn't a traditional CMO role—it is a chance to build a clinical model from the ground up at the frontier of healthtech and insurance.

About this role

Role overview

As the founding Medical Director, you will serve as the clinical backbone for the UK’s first AI-native digital health insurer. You will own clinical governance, shape automated triage architecture, and lead the path toward MHRA Class IIa medical device classification. This is a builder’s role at the intersection of AI and healthcare.

About the company

Ollyinsurance

Ollyinsurance

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'll do

What you will do

  • Design and sign off on AI-native clinical triage architecture and evidence-based care pathways across multiple specialties.
  • Lead clinical input for MHRA Class IIa medical device classification and ensure high-grade regulatory compliance and patient safety.
  • Build and manage relationships with clinical advisors and external care providers to scale the clinical function from zero to launch.

Who you are

Who this is a fit for

  • GMC-registered physician with a license to practise and a background in general practice, urgent care, or digital health.
  • Proven experience in clinical governance, risk management, or navigating MHRA/UKCA medical device regulations in a digital health context.
  • An entrepreneurial builder mindset comfortable with early-stage ambiguity and a deep interest in the intersection of AI and consumer health.

Why this role

Why this role is remarkable

  • Join a YC-backed founding team with leadership experience from Lemonade, AXA Health, and Cleo at a critical pre-launch stage.
  • Directly influence the clinical model of a disruptive insurance product targeting the 88% of the UK population currently without private cover.
  • High-impact leadership opportunity involving foundational equity and the chance to define how AI safely replaces manual clinical processes at scale.

Jack & Jill

How Jack & Jill work together

Jack
I get to know what you’re great at, then find roles you’d never find yourself.
Jill
I recruit from Jack’s network and make the intro when I spot a great match.

Meet Jack

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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.

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.

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