Job Application for Customer Service Representative, Member Care (Part-Time/ 11am-4pm EST) at Sidecar Health

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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.

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Accepted file types: pdf, doc, docx, txt, rtf

Are you located in Florida, Georgia, North Carolina, Ohio, Texas, or Utah?

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Are you available for a Monday–Friday: 11:00 AM - 4:00 PM Eastern Time shift?

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Are you available for a 11/16 start date and available for 4 weeks of paid training from 9:00 AM - 5:30 PM Eastern Time?

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Do you have, or can you set up before training begins on November 16, a reliable high-speed internet connection and a private, quiet workspace where you can give your full attention to member calls and chats during all training and shift hours?

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Are you willing to complete a background check if you are offered a position? Employment is contingent on satisfactory results.

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As the next step in our process, you’ll be asked to complete a 20-minute online Gorilla assessment. Are you willing to complete it?

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Do you speak Spanish (speaking and writing)? This is helpful for the role but not required to apply.

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Were you referred to this role by someone at Sidecar Health?

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If you were referred, which Sidecar Health employee referred you?

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Sidecar Health’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

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Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

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

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