Seasonal Agent Support Supervisor

About Us

We are a highly profitable, fast-growing healthcare startup—a small and mighty team of 230 helping people find and enroll in individual health coverage. To date, we’ve helped over 20 million people enroll in health coverage. We're a mission-driven team that advocates for and cares deeply about the people we serve.

We're a double bottom-line company: revenues and enrollments. The ACA brings high-quality, comprehensive, affordable health coverage within reach for low-income Americans, and we exist to make that promise a reality. Your contribution will help millions of people navigate the complex and confusing health insurance industry and enable them to access health care when needed.

We are committed to building a team that is well-balanced in representation to best serve the people who use our products. We believe in creating inclusive and equitable spaces that build trust and respect and foster a sense of belonging. These values are at the core of our culture and will continue to lead our organization to successful outcomes.

HealthSherpa is a fully remote company and was recognized as a 2026 Best Remote Place to Work by Built In, reflecting our commitment to building a people-first culture rooted in trust, flexibility, and impact.

About The Role

We are looking for individuals with management experience, experience providing detailed troubleshooting assistance, integrity, and strong interpersonal skills to join our Agent Support team for a seasonal contract opportunity. You will be fully remote and you will need reliable internet access for the duration of the role. Joining HealthSherpa will give you the opportunity to gain expert level knowledge within the health insurance industry. You will manage 10-12 remote support staff, report to a Manager on your team and work with us through the end of December 2026. There is a possibility of a term extension into January 2027 if Open Enrollment is extended.

Check out this video to get a snapshot of who we are: https://www.youtube.com/watch?v=xB7HrDusl8E

Please note we are only hiring employees in Florida, Ohio, Tennessee, Texas, Utah, or Virginia.

You Will

• Monitor and analyze individual and team performance metrics (e.g. AHT, CSAT, QA scores) to identify coaching opportunities and workflow adjustments.

• Provide support and leadership and ensure productivity amongst our seasonal support staff

• Provide feedback to seasonal support staff on inbound phone calls, online chats, and email communications

• Support the Team Manager with daily team management

• Handle first level escalations

• Collaborate with cross-functional teams (e.g. QA, Training, Management) to surface support trends and implement process improvements

You Have

• Residency in Florida, Ohio, Tennessee, Texas, Utah, or Virginia

• 2+ years of previous customer service management experience

• 5+ years of combined education, work, and/or volunteer experience

• A dedicated space to work remotely that has room for a desktop monitor and other provided equipment

• A work space that is free of background noise and distraction to provide information privacy

• Reliable home internet with download speed exceeding 128Mbps

• Bonus: Previous experience in a call center environment

What We Offer (Seasonal Employees)

• Fully remote employment

• Hourly wage: $20 ($21 for bilingual in Spanish)

• Computer and equipment for the duration of the role

• Monthly internet stipend

• Paid training

• Performance-based bonus opportunity

• Overtime opportunities

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What We Offer (Full-time, Not Temporary/Not Seasonal)

• Remote-first company (US-based remote only)

• Great compensation package at a high-growth, profitable company

• Excellent benefits package that includes health, vision, and dental coverage for you, your spouse, and dependents

• HSA/FSA options with corresponding contribution limits

• Monthly grocery stipend and home internet reimbursement

• 401K w/ a match after a grace period

• Life and AD&D coverage

• Disability insurance (Short and Long Term)

• Parental leave

• Four (4) weeks of paid vacation in addition to paid holidays

• Home office budget for remote team members

• Mental health and other wellbeing support programs through a partner network
  

As an organization, we value creating an inclusive and accessible experience. If you require reasonable accommodations during the application or interview process, please let your recruiter know.

We welcome and encourage people of diverse backgrounds, experiences, identities, abilities, and perspectives to apply. We are an equal-opportunity employer and a fun place to work. Come join the team at HealthSherpa!