Seasonal Agent Support Supervisor

We are a very profitable and fast-growing healthcare startup—a small and mighty team of 200 helping people find and enroll in ACA health coverage. As the largest health insurance exchange for the ACA, enrolling more individuals than healthcare.gov and all our competitors, we have helped over 15 million people enroll in health coverage to date through 2024. 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 in ACA coverage. 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 hundreds of thousands 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 balanced in representation to serve best 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.

We are looking for individuals with management experience, attention to detail, adaptability, 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 6-10 remote support staff, report to a Manager on your team and work with us through the end of December 2025.

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.

• 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.

• 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

• Bonus: Previous experience in a call center environment

• 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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• 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

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!