Field Support Representative

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

We're hiring a Field Support Representative to be the face of Sidecar Health for our members across the Columbus, OH area. This role requires that you currently live in or near the greater Columbus, OH area. You'll split your time between remote member care work (calls, chats, emails) and in-person visits to client worksites—helping members understand their benefits, solving problems on the spot, and making sure people get the care they need.

This is a remote-first role with regular local travel—you're not tied to an office, but you will be out in the field building relationships face-to-face.

Compensation: $54,000 year + equity, plus full benefits (details below).

What You'll Do

• Visit client groups onsite across Ohio, providing in-person support to members navigating their Sidecar Health plans
• Serve as the go-to in-person resource for client groups after enrollment and during periods of higher need
• Partner with our Account Management team to build strong relationships with key contacts and HR departments at client groups
• Handle day-to-day member care remotely—calls, web chats, and emails—with fast, friendly, effective service
• Build genuine rapport with members so every interaction feels personal, not transactional

What You'll Bring

• Reliable personal transportation and comfort with travel (up to 30%), with longer trips being about a 3-hour drive one way—fully reimbursed
• Strong communication skills and the ability to work independently without a lot of oversight
• A proactive, solutions-first mindset—you see a frustrated member as a problem to solve, not a complaint to escalate
• Genuine empathy and people skills—you build trust quickly and put people at ease
• Flexible availability to meet members where and when they need you
• Bilingual—a plus
• Healthcare or insurance experience—a plus

What You'll Get

• Competitive salary $54,000 + equity package
• Comprehensive Medical, Dental, and Vision benefits with no waiting period
• A 401k retirement plan
• Paid vacation and company holidays
• Real growth opportunities—this is a high-visibility role with room to move into new opportunities as you prove yourself