Customer Service Representative, Member Care

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.

Start Date and Training

• Start date: November 16
• Paid training: 4 weeks, 9:30 AM-6:00 PM ET. Attendance is required for the full training period.

Available Shifts (Eastern Time): 

• 8:30 AM-5:00 PM, Monday-Friday
• 9:00 AM-5:30 PM, Monday-Friday
• 10:00 AM-6:30 PM, Monday-Friday
• 11:30 AM-8:00 PM, Monday-Friday
• Mon, Thu, Fri: 9:30 AM-6:00 PM | Sat, Sun: 9:00 AM-5:00 PM (off Tue and Wed)
• Mon, Tue, Wed: 10:30 AM-7:00 PM | Sat, Sun: 9:00 AM-5:00 PM (off Thu and Fri)

*You must be available for one of the following shift options (your shift will be confirmed before you join)*

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), annual bonus opportunity, and an equity package
• 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
• Dental and vision with 100% of your premium covered, and 80% covered for your dependents
• A 401(k) retirement plan
• Paid time off, company holidays, and paid parental leave
• 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