Customer Service Representative, Member Care

February 20, 2026

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Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who are drive to make a difference. The passionate people who make up Sidecar Health's team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

Our Member Care team is at the forefront of our business. Their role is easily the most important: supporting our members on their healthcare journeys. We're growing our team and looking for warm, passionate people to join us and help deliver the best experience in healthcare. Your job will be to help our members - to answer their questions, help them solve problems, and ensure they have access to the care they need. As a startup, there is no shortage of opportunities, responsibilities, and growth! You'll work alongside a dynamic team that is disrupting the healthcare industry and having a positive and meaningful impact on our members' lives every day.

Job Responsibilities:

Handle inbound calls and chat boxes from our members in regard to Sidecar Health's products and services

Provide excellent customer service in a timely and positive manner

Build rapport and maintain positive relationships with existing members to understand their needs and ensure a memorable member experience

Handle issues and complaints where appropriate

Maintain policies and standard operation procedures

Requirements:

Adaptable and resilient - you thrive in a fast-moving, ever-changing startup environment
People-first communicator - you listen with empathy, connect easily, and meet members where they are
Clear and confident in both written and spoken communication, with the ability to answer questions in the moment
Detail-oriented problem solver - you spot the small things and think creatively to help members navigate their plans
Education: High school diploma or equivalent required; bachelor's degree preferred
Bilingual in English and Spanish
Experience in healthcare or insurance (preferred)
Available for one of three shifts options (Central Standard Time) 7:30 AM – 4:00 PM, 8:00 AM – 4:30 PM, 8:30 AM – 5:00 PM

Sidecar Health adopts a market-based approach to compensation, where base pay varies depending on location and is further influenced by job-related skills and experience. The current expected hourly rate for this position is $17.00-$19.00 + medical, dental, vision, and 401k.

Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.

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