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Business Operations Lead

New York, United States
Mar 25, 2021
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Apply before: 
Sep 21, 2021

Why We Exist

Every morning, 10,000 Americans wake up and begin their first day of retirement. Chapter is re-inventing the way that Americans transition into retirement, starting with Medicare.

For most people, Medicare is boring, bureaucratic, and confusing. Unlike employer-sponsored health coverage, most people aged 65 and older must choose when to sign up for Medicare and then select specific coverage from more than 45 options available in each county.

This problem is important because navigating Medicare is frustrating and confusing. If people wait too long to choose coverage, they risk life-time penalties from Uncle Sam, may need to undergo medical underwriting, or may pay out-of-pocket for 20%+ of medical costs plus prescriptions and most costs of dental, vision, and hearing.

What We Do

Our team and technology help retirees to navigate Medicare, including when and how to sign up, what specific coverage to choose, and how to maximize the benefits from their coverage.

Chapter has built industry-leading technology to help retirees save thousands of dollars on their healthcare. Our promise is simple: we want people to improve their health coverage while reducing what they pay for it.

How? Our platform searches every Medicare option available nationwide, while others search only a subset of plans, which is the norm in the Medicare market.

This full search is why we find savings and benefits that others miss.

Our Team

Our team is high-integrity and high-horsepower with a big heart.

We are software engineers, illustrators, lawyers, and former management consultants. We have worked at organizations including Palantir, Axios, Latch, and McKinsey.

We’re equally proud of our work as guides at history museums, gophers at radio stations, Karate instructors, coaches at debate camps, and public defenders for the under-represented.

The Role

We are looking for an Operations Lead to join our core team. Reporting to our co-founder and Chief Operating Officer, you will be one of our first ten team members and will help to shape our culture, processes, product, and strategy. You will also work closely with our team of Medicare Advocates and our Director of Education and Partnerships, along with our product teams.

This role requires a high ownership-orientation and has responsibilities that are significantly broader than a typical operations role. We prefer that this role be based in New York, with the ability to travel ~1-2 weeks every two months.

You will help to drive four objectives along with our COO:

  • Accelerate growth across new partnerships and channels
  • Maximize the effectiveness and efficiency with which our Medicare Advocates and our technology serve our members
  • Fortify our supply-side relationships with insurance carriers, technology partners, and other vendors
  • Lead priority company objectives


  • Accelerate Growth

    • Help identify and execute new enterprise partnerships
    • Develop and deploy a process for rapid implementation of new partnerships, working closely with our growth and product teams
    • Support our team of Medicare Advocates and Director of Growth and Education to accelerate our existing pipeline of partnerships
  • Maximize operational efficiency

    • Map each step of our member journey and identify high-value steps and user problems that we can productize to improve (a) the delight of our members and (b) the efficiency of our Medicare Advocates
    • Identify potential technology solutions to maximize delight and efficiency, and lead evaluation of build vs. buy options
    • Implement new processes and solutions, largely with our growth lead and team of Medicare Advocates
  • With our senior Medicare Advocate, re-design our training, on-boarding, and education for new Medicare Advisors

  • Fortify supply-side relationships

    • Maintain and expand our relationships with insurance carriers
    • Manage our insurance licenses along with our COO and team of Medicare Advocates
    • Identify and help implement new capabilities from technology vendors and partners
  • Lead priority company objectives

    • As new initiatives arise, you will own building out the processes to enable us to achieve or objectives efficiently as we scale

What you'll need to be successful

  • 2-5 years experience in an early-stage company as a high-performing generalist or experience in consulting, investment banking, investing, or product execution
  • Exceptional aptitude at defining both high-level objectives and the granular steps required to achieve those objectives. This means you have an excitement to shape strategy but an even stronger desire to execute end-to-end on that strategy
  • Strong ability to persuade through influence, evidence, and intuition (not authority)
  • Positional empathy: You naturally empathize with both our members and Medicare Advocates alike (who are internal users of our product), articulating their needs and problems clearly
  • Ownership orientation: You are excited to set goals and have ownership for hitting those goals with a team committed to our collective success
  • Excellent quantitative intuition, with experience in Excel or financial modeling
  • Comfort with ambiguity: While starting from a blank slate is challenging, you find it exciting, rewarding, and empowering.
  • High-integrity, first-principles thinker: We don’t care how others have done things; we want to do things the right way
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