Chief Of Staff

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.

Team

MedBill AI

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.

About the role

Chief of Staff

We are seeking a highly motivated and organized Chief of Staff to support our founder/CEO. You will be the CEO’s force multiplier, partnering on a day-to-day basis to support high-priority topics and drive strategic initiatives. The ideal candidate is a proactive, strategic thinker passionate about enhancing organizational efficiency and supporting executive leadership in achieving business goals. If you thrive in a fast-paced, innovative environment and are eager to make a significant impact, we want to hear from you.

What You'll Do

• Act as a strategic advisor and liaison to the CEO, helping to execute the company’s highest priorities while working on long-term special projects and strategic initiatives.
• Plan and prepare leadership, board, and all-hands meetings. Ensure that goals are understood, agendas are followed, and action items are delegated with appropriate follow-up.
• Develop, implement, and improve frameworks for company-wide and team-specific goal setting and measurement in line with the company vision and strategy.
• Build and develop relationships with all team members for increased efficiency and effective responsiveness regarding existing operations and help to define new operational strategies.
• Enhance operational processes and company culture to support our rapid growth.
• Support the CEO in hiring, recruiting, and onboarding top talents.
• Help craft business development materials and manage relationships with prospects and partners.
• Take on additional responsibilities as needed to support company objectives.

About you

• Experience as a consultant, founder, Chief of Staff, or in operations, preferably within the healthcare and/or technology industry.
• Have strong project management skills with a proven track record of delivering successful initiatives.
• Detail-oriented and excellent analytical, problem-solving, and organizational abilities.
• Experience in business and operational development, with enthusiasm for identifying and addressing structural gaps.
• Proficiency in managing OKRs and KPIs, using metrics to drive performance and support key decisions.
• Exceptional communication, listening, and negotiation skills, with the ability to convey complex information clearly.
• Adaptability to wear multiple hats, viewing challenges as opportunities, and thriving in a fast-paced environment.
• Excitement about developing structure where it is lacking and contributing to the company's growth.

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

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.