Medicare Advisor

Propel•New York, NY

4d•$70,000 - $80,000•Remote

About The Position

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 healthcare 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 EPD (engineering, product, design) team to refine how we support users in navigating government healthcare. This role requires someone who is comfortable using AI tools in their daily work to research plans, draft communications, summarize complex information, and improve personal productivity. You should be an enthusiastic and capable user of modern AI-powered tools.

Requirements

Fast learner with a strong interest in developing expertise in Medicare/Medicaid nationwide.
Comfortable using AI tools (such as ChatGPT, Claude, or similar) in daily work for tasks like research, drafting, and problem-solving. Willingness 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 consultations.
Have or are willing to obtain an active broker/agent health insurance license in your home state and additional non-resident state licensure (company-sponsored).
Willing to complete training and take tests relevant to getting appointed by health insurance carriers.
Excellent communication skills with the ability to explain complex concepts simply.
A comprehensive understanding of the difficulties faced by low-income Americans and a dedication to offering compassionate and tailored assistance.
From October 15th through December 7th (the Annual Enrollment Period), refrain from taking vacation and be able to take phone/chat shifts on the weekends (likely 1 day/weekend during that period).
Must pass a background check as part of the hiring process.

Nice To Haves

Experience using AI tools to improve personal workflow efficiency (e.g., using AI for research, drafting emails, summarizing documents, or comparing data).
Fluency in Spanish.
Prior experience in healthcare, insurance, benefits counseling, or customer service roles.
Experience working at a startup or tech company.

Responsibilities

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 healthcare 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, including feedback on AI-assisted features.
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.

Benefits

Remote-friendly work environment with a dog-friendly office in Downtown Brooklyn. The team meets in-person for optional retreats.
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

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