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This position was posted on January 8, 2026 and is likely no longer accepting applications. We've kept it here for historical reference. Check out the similar jobs below!

Job Overview
Location
Remote
Job Type
Full-time
Category
Customer Support
Date Posted
January 8, 2026
Full Job Description
đź“‹ Description
- • Be the human face of a company that is reinventing health insurance for millions of Americans. As a Customer Service Representative on Sidecar Health’s Member Care team, you will serve as the first—and often most memorable—point of contact for members navigating everything from choosing a doctor to understanding a claim. Every conversation you have will directly shape how people feel about their healthcare and about Sidecar Health.
- • Own the member journey from hello to resolution. You will field inbound calls, live chats, and emails from members across the country who need help understanding benefits, locating in-network providers, submitting receipts, or simply calming fears about an upcoming procedure. By the end of each interaction, members should feel heard, informed, and empowered to make confident healthcare decisions.
- • Master Sidecar Health’s innovative model so you can translate complex insurance concepts into plain language. You will become fluent in our fixed-benefit structure, explain how our payments differ from traditional copays, and show members how to maximize their Sidecar Health card at pharmacies, labs, imaging centers, and doctor’s offices nationwide.
- • Turn problems into loyalty. When a claim is denied, a card is lost, or a provider refuses to accept our payment, you will investigate the root cause, coordinate with internal teams (Claims, Provider Relations, Product, Engineering), and follow up until the member’s issue is fully resolved. Your case notes will feed directly into product improvements that prevent the same pain point for future members.
- • Champion empathy at scale. You will build genuine rapport with a diverse member base—tech-savvy millennials, retirees on fixed incomes, gig workers, and families managing chronic conditions. Using active listening and cultural sensitivity, you will tailor your tone and guidance to each caller’s comfort level and literacy.
- • Drive continuous improvement. After every shift, you will log trends you noticed—confusing web copy, glitchy app flows, or provider misinformation—and present quick-win suggestions in weekly retros. Your frontline insights will influence roadmap priorities and help Sidecar Health stay ahead of member needs.
- • Collaborate in a fully remote, high-growth startup. You will join daily stand-ups on Zoom, brainstorm in Slack channels, and celebrate wins in virtual shout-outs. Despite the distance, the team culture is tight-knit; expect GIF wars, coffee-roulette pairings, and quarterly in-person meetups when safe.
- • Grow your career at startup speed. Top performers move into Senior Representative, Team Lead, or specialized roles in Training, Quality Assurance, or Member Insights within 12–18 months. We promote from within and give you stretch projects—like building a new call-flow or piloting an AI chatbot—to prove you’re ready for the next step.
- • Protect member privacy like a vault. You will handle PHI daily and must follow HIPAA, SOC-2, and internal security protocols without exception. One slip could erode the trust we’ve spent years earning, so vigilance is non-negotiable.
- • Celebrate impact daily. At the end of each week you’ll see metrics—CSAT, first-call resolution, average handle time—improve because of your work. Even more rewarding are the thank-you cards, five-star reviews, and stories from members who finally got the care they needed thanks to your guidance.
Skills & Technologies
About Sidecar Health Insurance Agency, Inc.
Sidecar Health offers individual and family health insurance plans in the United States. The company provides fixed-indemnity coverage allowing members to pay upfront for medical services and submit receipts for reimbursement. Policies are underwritten by insurers such as Companion Life and Sirius America, and distributed through licensed agents. Sidecar Health operates as a technology-enabled platform for direct-to-consumer enrollment, account management, and claims processing, targeting consumers seeking alternatives to traditional major medical coverage.
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