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

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

Medicare Agency Director

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