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Posted Apr 16, 2026

[Remote] Medicare Advisor

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Note: The job is a remote job and is open to candidates in USA. Propel is a technology company that strengthens the social safety net in America. As a Medicare Advisor, you will help users compare Medicare plans and maximize their healthcare benefits while collaborating with the engineering, product, and design teams to enhance user experience. 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 - 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 Skills - 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 - Fluency in Spanish - Prior experience in healthcare, insurance, benefits counseling, or customer service roles - Experience working at a startup or tech company Benefits - 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 Company Overview - Propel is a tech company that’s strengthening the social safety net for people who receive government benefits. It was founded in 2014, and is headquartered in Brooklyn, New York, USA, with a workforce of 51-200 employees. Its website is https://www.propel.app/.
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