Medicare Advisor

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.

Propel serves approximately 1M users who are Medicare eligible, most of whom are also Medicaid eligible. We are building the first-ever app‑based brokerage focused on helping “duals” (Americans on Medicare and Medicaid) enroll in health care plans. We specialize in Dual‑Eligible Special Needs Plans (D‑SNPs) and are expanding to 30 states in 2026, with plans to move into larger Medicare markets over the next 24 months.

As a Medicare Advisor, you will be a trusted expert, helping users compare Medicare plans, enroll with confidence, and maximize their healthcare benefits. You will also collaborate with our engineering, product, and design (EPD) team to refine how we support users in navigating government healthcare.

This role requires someone who is comfortable using AI tools in daily work to research plans, draft communications, summarize complex information, and improve personal productivity.

• Respond to incoming inquiries from users regarding D‑SNPs, Traditional Medicare, Medicare Advantage plans, and Medicaid, providing expert guidance and support via in‑app chat (primary) and phone (secondary).
• Use AI‑powered tools to efficiently research plan details, compare coverage options, and synthesize complex regulatory information for users.
• Apply a user‑centric approach, prioritizing user needs and exceeding service expectations.
• Conduct comprehensive comparisons of Medicare Advantage plans, ensuring users understand their options for health care coverage based on their specific needs.
• Educate users on eligibility requirements, enrollment processes, and Medicare compliance, helping them navigate the complexities of healthcare regulations.
• Execute enrollment applications accurately, providing users with critical information about deadlines and ongoing actions needed to sustain their coverage effectively.
• Maintain appointments with multiple insurance carriers across 30+ states and ensure compliance with licensing requirements as Propel expands its D‑SNP footprint.
• Collaborate with product, design, and engineering teams to improve app functionality, offering insights from user interactions and enrollment experiences.
• Leverage AI tools to draft user communications, create summaries, and identify patterns in user inquiries that can inform product improvements.
• Offer constructive feedback to enhance user and agent experiences within the application workflow.
• Flex outside of core D‑SNP advisory as needed, supporting broader Medicare enrollment efforts, general app CX, and other team initiatives as we scale into new states and markets.

• You prefer a highly structured environment with established workflows and detailed guidance for every situation.
• You do best with consistent, close oversight before taking action.
• You are looking for a role where the scope of your work is unlikely to change.
• You are not comfortable using technology or AI tools as part of your daily workflow.

• Fast learner with a strong interest in developing expertise in Medicare/Medicaid nationwide.
• Comfortable using AI tools (e.g., ChatGPT, Claude, or similar) in daily work for tasks such as research, drafting, and problem‑solving; willing to learn and adopt new AI‑powered tools as they are introduced.
• Able to handle complex user inquiries and multitask while receiving information from a user, including researching health plans and concepts.
• Quickly develops credibility with users, demonstrating an aptitude for active listening, deep knowledge in the area you are advising them on, and providing confident…