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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. Interested in working at HealthSherpa but don't see the right role for you? We'd love to hear from you! Our people are what make the difference and we want to meet you if you're the kind of person who wants to make an impact on access to healthcare and individual lives. Our team will keep your information on file and reach out when there's a role that is the best fit for your experience and what you're looking for. 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!