Medicare Agency Director

Medicare Agency Director ABOUT US: Propel builds technology that strengthens the social safety net in America. We envision a future where every American has the tools and resources they need to thrive. The safety net’s strength depends not just on funding, but delivery. Propel exists to dramatically improve how government benefits are delivered. Recertifying SNAP, picking a D-SNP plan, or protecting against EBT theft should feel as seamless as Apple Pay or Netflix. Governments struggle to build modern, scalable user experiences. We don’t. To succeed, we focus on execution. We’re building the technology, required to deliver modern benefits experiences at scale. We aim to massively grow impact and revenue while operating with a lean and excellent team, which requires rigor, urgency, strong judgment, and thoughtful use of modern technology, including AI. Over 5.5 million Americans trust Propel today. We’ve grown revenue 35% YoY and are reinventing entire benefit categories, including Medicare, around the real needs of low-income Americans. We’re building a high-growth, high-ceiling, sustainable for-profit company where impact drives revenue. THE ROLE: We are seeking a Medicare Agency Director to lead and scale Willoughby, Propel’s licensed Medicare brokerage. Willoughby is building the first app-based, AI-enabled Medicare agency, initially focused on dual Medicare/Medicaid beneficiaries, a historically underserved and complex population. This role operates as the business leader of the agency. You will own strategy, growth, financial performance, compliance, and team leadership as we scale from post-incubation to a category-defining business. This is a rare opportunity to build a modern, technology-enabled brokerage in one of the most regulated and impactful sectors of healthcare. WHAT YOU’LL OWN: STRATEGY & FINANCIAL PERFORMANCE - Define and execute a multi-year growth strategy targeting 5-7x enrollment growth by the end of 2026 - Own full P&L responsibility, including forecasting, budgeting, and performance reporting - Lead executive-level business reviews and cross-functional alignment GROWTH & MARKET EXPANSION - Partner with Marketing to scale acquisition across digital and partner channels - Optimize full funnel performance - acquisition, conversion, and retention - Own carrier relationships, FMO partnerships, licensing strategy, and commercial negotiations for vendors and partnerships that enable business growth OPERATIONS & PRODUCT - Lead cross-functional execution across product and operations - Scale efficiently through AI, automation, and data-driven workflows - Drive product strategy and platform expansion (pushing presence beyond mobile app to web) - Prioritize improvements using operational and funnel metrics COMPLIANCE & REGULATORY EXCELLENCE - Define and oversee a best-in-class Medicare compliance program - Ensure operational rigor in a CMS and carrier-regulated environment TEAM LEADERSHIP - Build and develop a high-performing, mission-driven team - Foster a culture of ownership, urgency, and deep empathy for low-income beneficiaries WHAT WE’RE LOOKING FOR - 7+ years of leadership experience in product, operations, business development, or general management - Experience scaling a business from incubation to meaningful revenue - 3+ years of Medicare experience (agency, carrier, or health-tech preferred) - Demonstrated P&L ownership and strong financial judgment - Comfort operating in regulated, evolving policy environments - High ownership mindset, strong executive presence, and exceptional attention to detail - Deep motivation to improve healthcare access for low-income Americans WHY THIS ROLE MIGHT NOT BE FOR YOU This role may not be a fit if you: - Prefer highly structured environments with predictable planning cycles - Want a narrowly scoped leadership role rather than broad business ownership - Are uncomfortable with regulatory complexity and policy-driven change - ... (truncated, view full listing at source)