Why Chapter Exists

Every morning, 11,000 Americans wake up and begin their first day of retirement. While retirement should be an exciting, empowering, and fulfilling part of one’s life, the reality today is that retirement brings along with it a fundamentally new set of challenges that make it an overwhelming time for many.

At Chapter, we believe that the current infrastructure for retirement is broken, and we’re on a mission to fix it. We’ve started by building industry leading technology to solve the first major obstacle in retirement: navigating Medicare (healthcare coverage for retirees over 65). Our products help seniors sign up, choose an insurance plan, and leverage their plan after they are enrolled. And, unlike most Medicare advisors who only search plans that pay them, Chapter searches every Medicare option nationwide. This allows us to find savings and benefits that others miss.

But our ambition doesn’t stop with Medicare — we seek to transform the way that Americans navigate and experience retirement. If this sounds exciting to you, we’d love to speak with you.

Current Job Openings

Demand Generation



Partnerships Lead
New York, New York, United States

Member Enrollment and Support

Member Support

Manager, Member Success & Growth
New York, New York, United States


Data Scientist
New York, New York, United States


Product Designer
New York, New York, United States


New York, New York, United States

Product Management

Growth Product Manager
New York, New York, United States