Head of Product


We are building an AI assistant that saves consumers time and money on medical bills, health insurance and benefits, and healthcare.

Medical bills are a massive problem. They are confusing, over 40% contain errors, 17% of claims are denied by insurance, and often represent very large sums of money. As a result, 100 million Americans are saddled with medical debt, and medical bills cause nearly 70% of personal bankruptcies in the US.

Dealing with unexpectedly high medical bills is time-consuming, complex, and stressful. Stuck between their providers, payers, and bill collectors, consumers too frequently have to make numerous phone calls, wait on hold, and even send paper letters and faxes. Appealing insurance denials, resolving billing errors, negotiating bills, and filing out of network claims require expert knowledge that most consumers don't have.

Thanks to AI and new healthcare regulations around data access and price transparency, we can now automate this soul-crushing work and empower consumers to fight back against this broken system. Beyond medical bills, we help people through their entire healthcare journey as they pick their health insurance plans and benefits, or look for care that fits their budget.


MedBill AI is founded by 2 Oscar Health veterans, the first health insurance company built around a full stack technology platform and a relentless focus on serving its members. We joined Oscar pre-product, stayed through the IPO and helped it grow to over 1M members. We've worked across Oscar's entire stack and led many key projects, including its in-house telemedicine platform and claim system, positioning us uniquely to take on MedBill AI. We're proud of how Oscar raised the bar for what people should expect from their health insurance, and we’re excited to have an even larger impact with MedBill AI by taking the side of consumers unequivocally, regardless of their health insurance.

We’re lucky to be backed by the founders, investors, and operators at Hugging Face, Oscar Health, TrueBill, Sunrise, RRE Ventures, Red Sea Ventures, Index Ventures, and much more.

About the role

As Head of Product, you will join as a founding team member and lead our product toward product-market fit at the intersection of technology, healthcare, and consumer advocacy. This pivotal role encompasses product vision, strategic leadership, and operational management, directing innovative solutions that address the most critical pain points in medical billing and health insurance.

What You'll Do

  • Strategic Leadership: Forge a forward-thinking product strategy in close partnership with the CEO. Lead efforts to leverage the most advanced technologies to automate issue resolution processes, delivering on our promise to alleviate the burden of medical billing.

  • Product Leadership: Take full ownership of guiding our product to market fit. Manage the entire product lifecycle from initial concept to successful market launch. You will spearhead product development, conduct user research, strategize launches, and utilize analytics to ensure success. Your role will be pivotal in scaling the product team as the company grows.

  • Operational Excellence: Build and refine robust operational workflows by leveraging technology for process enhancement, setting a standard for operational excellence in healthcare tech.

  • Advocacy and Expertise: Partner with our team of Health Advocates, enhancing their capabilities to tackle complex billing issues effectively and advocate for consumer rights with expertise.

About you

  • Have over 10 years of product management experience, with a substantial focus in the healthcare sector.

  • Demonstrate proven leadership in product strategy and operational excellence.

  • Are scrappy and hands-on, ready to engage deeply in product and process details to drive significant change.

  • Thrive in a dynamic, entrepreneurial environment and adept at managing complex challenges daily.

  • Are deeply committed to transforming healthcare accessibility and reducing the complexities of medical billing.

  • Seize professional growth opportunities as the company expands its impact and reach.

P.S. This is a list of ideal qualifications for this position. If you don't meet every single one of them, you should still consider applying!

How to apply

If the above piques your interest, and you’re into working in a demanding environment with high ownership, wide scope, and big impact, we want to hear from you.

To apply, email us directly at careers@medbill.ai. Please include the role in the subject line; in the body of the email, please include links to help us learn more about you and your work (LinkedIn, resume, Github, personal website, etc.).