Medicare Agency Director

Propel

2d • Remote

About The Position

We are seeking a Medicare Agency Director to lead our newest line of business through its post-incubation scaling phase. You’ll report directly to our GM, Healthcare.

Propel owns Willoughby, a licensed entity building the first app-based digital Medicare brokerage, initially focused on dual Medicare–Medicaid users. The Director will continue to build Willoughby into an industry-leading agency, combining strong financial performance with exceptional member service, by applying modern consumer technology, such as AI and automation, to sustainably serve low-income populations.

Requirements

• 7+ years of product, project management, operations, and/or business development experience
• Has led teams through projects from incubation to mass scale
• 3+ years of experience in Medicare: tech, product design, or agency operations are a plus
• Exhibits extreme ownership and acute attention to detail – you don’t let anything slip through the cracks
• Experience working directly with a founder team and/or managing key executive leadership stakeholders
• Highly motivated by helping low-income Americans on government sponsored healthcare programs

Responsibilities

• Set and execute Medicare agency strategy, partnering with the GM of Healthcare and Strategy & Ops to define a 3-year plan, annual OKRs, and a GTM strategy that drives 5–7x enrollment growth by 2026
• Own financial performance, including P&L, budgeting, long-range financial modeling, and monthly business reviews with senior and cross-functional stakeholders
• Build and scale the brand and growth engine, partnering with Marketing to establish the agency brand and drive top-of-funnel demand across digital, advisor-assisted, and partner channels
• Lead cross-functional operations and execution, aligning product, operations, and growth roadmaps while scaling efficiently through automation and AI
• Expand market access and partnerships, owning state licensing and carrier appointment strategy, and deepening relationships with carriers, FMOs, and technology vendors (including commercial negotiations)
• Drive product strategy and platform expansion, using funnel metrics to prioritize high-impact bets, championing an AI-first roadmap, and leading expansion from mobile to web
• Ensure regulatory excellence, defining compliance strategy and overseeing the development of an industry-leading in-house compliance program in partnership with Ops and external experts
• Build and lead a high-performing team, hiring and developing cross-functional leaders while fostering a culture of ownership, empathy for low-income beneficiaries, and continuous learning

Benefits

• Meaningful work and a strong shared sense of mission
• Remote-friendly work environment with a dog-friendly office in Downtown Brooklyn. The team meets in-person for optional retreats a few times per year.
• 20 Days of PTO
• 4% 401K match
• $10k lifetime spend towards Carrot Fertility
• Excellent Medical, Dental and Vision options
• Other health and mental health focused benefits and perks

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed