Customer Service Representative, Member Care (Part-Time/ 11am-4pm EST)

About Sidecar Health
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 will make things happen.
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!
About the Role
As a Member Care Representative at Sidecar Health, you'll be the voice members turn to when they need help understanding their Benefit Amount, navigating their plan, or resolving issues with claims. You'll handle inbound calls, chats, and tickets with empathy and efficiency, helping members get the most out of a model that's nothing like legacy insurance. This is a front-line role where great service directly shapes how members experience healthcare.
*Location: Remote. Candidates must currently reside in Florida, Georgia, North Carolina, Ohio, Texas, or Utah*
Start Date, Shift Time, and Training
Start date: November 16
Shift time: 11:00 AM - 4:00 PM Eastern Time
Paid training: 4 weeks, 9:00 AM- 5:30 PM ET. Attendance is required for the full training period.
What You'll Do
Handle inbound calls and chats from members with questions about their Benefit Amount, plan benefits, and how to get money back when they choose lower-cost care
Resolve member issues and complaints with empathy, accuracy, and a positive attitude
Build rapport with members by listening carefully and meeting them where they are
Follow established policies and standard operating procedures while maintaining detailed, accurate records
What You'll Grow Into
Support process improvements as Sidecar Health's member base and product evolve
Take on expanded responsibilities across claims or member escalations as you grow within the team
Contribute to a startup culture where your feedback and ideas help shape how the team operate
What You'll Bring
People-first communicator who listens with empathy and can answer questions clearly and confidently in the moment, in writing and by phone
Detail-oriented problem solver who spots the small things and helps members navigate their plan creatively and thoroughly
Adaptable and resilient — you thrive in a fast-moving, ever-changing environment and stay steady when things shift
Strong customer service background; we have successfully welcomed people transitioning from clinical roles like CNAs who bring genuine care for others
High school diploma or equivalent required; bachelor's degree preferred
Nice to have
Bilingual in English and Spanish
Experience in healthcare, insurance, or claims processing
Familiarity with ticketing or chat support tools
Demonstrated interest in growing within a startup environment
What You'll Get
Competitive hourly wage ($20.00)
Medical coverage from day one, with 100% of the premium paid by Sidecar for you and your dependents. Choose an HSA-eligible plan or a $0 deductible plan
Stay connected: $50 a month toward your internet and $50 a month toward your phone, reimbursed through expenses
The opportunity to make an impact at a rapidly growing, mission-driven company transforming healthcare in the U.S.
Work Environment Requirements
A reliable, stable high-speed internet connection
A private, quiet, distraction-free workspace with minimal background noise, suitable for taking confidential member calls
The ability to give your full, uninterrupted attention to member calls and chats throughout your scheduled shift and training hours
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.