Medicare Agency Director

About Us

Propel is on a mission to empower low-income Americans by simplifying access to government benefits with modern technology. We're a passionate team of 100 Propellers - all working to help our users get through the month, every month.

The Role

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.

Here's how you'll impact the company:

Strategic & Financial Leadership

• 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

Brand & Marketing

• 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

Operations

• 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)

Product

• 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

Compliance

• 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

Team Building

• 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

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

At Propel, you'll enjoy:

• 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 
• Propel builds compensation bands referencing the 75th percentile of compensation for companies like us. Expected compensation for the role as scoped is $180,000 - $220,000 and will be based on how a candidate matches to our internal leveling guide.

Additional Considerations:

• We are committed to building a diverse and inclusive team, and welcome applicants from all backgrounds and abilities.
• We're currently accepting applications from the states we have an established entity, which includes California, Colorado, District of Columbia, Florida, Georgia, Illinois, Maryland, Massachusetts, New Jersey, New York, Oregon, Pennsylvania, Texas, Virginia, and Washington.
• Background Check Requirement: For roles with access to confidential employee or customer information, a background check may be conducted following a conditional offer. All background checks are handled in accordance with applicable laws, including the Fair Credit Reporting Act (FCRA).

More About Propel

Propel is a technology company that’s strengthening the social safety net for people who receive government benefits. Over 5 million Americans trust the free, modern Propel app to manage their government benefits, save money, and get updates when their benefits change. We’ve also partnered with renowned institutions and organizations like Vote.org, GoFundMe, and GiveDirectly. 

Propel is a for-profit, venture-backed company that holds its social mission at its core. We're proud to be supported by a blend of nonprofits, impact investors, and world-class investors, including the Robin Hood Foundation, Andreessen Horowitz, Nyca Partners, Financial Health Network, JPMorganChase, Kevin Durant, Serena Williams, and Nas.

Learn more about our impact from the press

• Fintech Company Propel Announces $10 Million Fund For Food Stamp
• Late Show With Stephen Colbert
• How to Propel the Fight Against Poverty in America
• How Tech is Helping Poor People Get Government Aid
• Propel Routes Money to those Who Need it Most
• How one tech startup is giving cash to SNAP recipients
• Recipients Affected By Government Shutdown
• How hunger relief groups say you can help feed your neighbors during the shutdown and beyond
• Helping our Users Navigate this Crisis

Join us, and let's build something amazing together!