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
  
  
• Prefer predefined career ladders over growth through ownership and stretch work
  
  
• Avoid ambiguity or cross-functional problem solving
  
  
• Are hesitant to rethink traditional models using AI and automation
  
  

If building a mission-driven, AI-enabled Medicare agency in a complex and evolving space energizes you, you’ll likely thrive here.

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).

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!