Medicare Agency Director

Propel•Brooklyn, NY

1d•$180,000 - $220,000•Remote

About The Position

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

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
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.