About the job
About Us
At Propel, we are dedicated to empowering low-income Americans by streamlining access to government benefits through cutting-edge technology. Our dynamic team of 100 passionate individuals, known as Propellers, is committed to assisting our users in navigating their monthly challenges.
The Role
We are in search of a Director of Medicare Agency to spearhead the growth of our latest business line as it transitions from incubation to full-scale operations. You will report directly to our General Manager of Healthcare.
Propel is the proud owner of Willoughby, a licensed entity that is pioneering the first app-based digital Medicare brokerage, with a special focus on dual Medicare-Medicaid users. In this role, you will guide the development of Willoughby into a leading agency, merging outstanding financial performance with superior member services by leveraging advanced consumer technologies such as AI and automation to effectively reach low-income communities.
Your Impact on the Company:
Strategic & Financial Leadership
- Develop and implement the Medicare agency strategy in collaboration with the GM of Healthcare and Strategy & Ops, establishing a three-year plan, annual OKRs, and a go-to-market strategy aimed at achieving 5-7x enrollment growth by 2026.
- Oversee financial performance, including P&L, budgeting, long-term financial modeling, and monthly business reviews with senior and cross-functional stakeholders.
Brand & Marketing
- Create and enhance the agency's brand and growth engine, working with Marketing to establish brand awareness and drive top-of-funnel demand across digital platforms, advisor-assisted channels, and partnerships.
Operations
- Direct cross-functional operations and implementation, ensuring alignment of product, operations, and growth roadmaps while scaling efficiently through automation and AI.
- Broaden market access and partnerships, managing state licensing and carrier appointment strategies, and strengthening relationships with carriers, FMOs, and technology vendors, including handling commercial negotiations.
Product
- Lead product strategy and platform expansion, utilizing funnel metrics to prioritize impactful initiatives, advocating for an AI-first roadmap, and overseeing the transition from mobile to web.
Compliance
- Guarantee regulatory excellence by defining compliance strategies and supervising the creation of a best-in-class in-house compliance program in partnership with Operations and external experts.

