Mission

The all-in-one service to save time, money, and stress on health insurance and medical bills.

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.

Team

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 and investors at Hugging Face, Oscar Health, TrueBill, CaseText, Forerunner Ventures, Red Sea Ventures, RRE Ventures, and much more. We are well-funded for the next few years.

About the role

As the Team Lead for our Customer Experience Operations, you will play a critical role in overseeing the workflows, quality, and outcome of our healthcare advocate team. Your focus will be on improving case resolution processes, enhancing customer communications, and identifying opportunities to scale efficiently while reducing operational costs. You will work closely with our product and engineering teams to inform and drive automation improvements while creating tools and templates that empower our advocates to succeed.

This role requires a strategic thinker who is deeply organized, capable of navigating complex systems, and comfortable pushing for higher quality in both team performance and product offerings. While healthcare industry experience is not required, a strong aptitude for organizing and optimizing operations across multifaceted challenges is essential.

Key Responsibilities

• Team Leadership & Management:

  Mentor healthcare advocates, providing feedback, coaching, and professional development. Ensure high-quality case resolutions through oversight and regular reviews while fostering a culture of excellence and accountability.

• Process Optimization:

  Refine workflows to manage tasks efficiently and minimize resolution times. Create and implement templates and standardized processes to scale operations and onboarding. Monitor metrics to identify inefficiencies and propose cost-effective solutions.

• Product & Strategy Collaboration:

  Understand product capabilities to identify opportunities for automation and efficiency. Represent team and user needs in product discussions, collaborating with engineering to prioritize initiatives that reduce workload.

• Data-Driven Decision Making:

  Measure operational costs and time investments to identify improvement areas. Use data to implement strategies and tools that lower costs and maintain quality. Create reports to track team performance and the impact of changes.

About you

• Strategic & Analytical: You excel at identifying inefficiencies and creating scalable systems to address them.

• Customer-Centric: You understand the importance of quality in customer communications and are dedicated to enhancing user experiences.

• Collaborative Leader: You’re a skilled team manager who inspires trust, fosters development, and drives high performance.

• Proactive Problem-Solver: You thrive in environments with a lot of moving parts, navigating complex challenges with creativity and focus.

• Education: Bachelor’s degree in Business Administration, Engineering / Math Degree, Operations Management, or a related field. Advanced degrees (such as MBA) are a plus.

• Experience: 2–4 years of professional experience in operations, consulting, customer experience, or similar roles requiring strategic problem-solving and cross-functional collaboration.

P.S. These are ideal qualifications, not minimums. If you don't meet some, you should still apply!