Medicare Advisor

Flourish Ventures; New York (NY); Hybrid; USD 70,000 - 80,000; Full time

Benefits offered by this job

Remote-friendly workplace

20 Days PTO

4% 401K match

Health, dental and vision benefits

Job summary

Propel is seeking a Medicare Advisor to help dual-eligible users compare plans, enroll, and maximize benefits. You’ll partner with the EPD team to refine how users navigate government healthcare while integrating AI tools to research plans and draft communications.

You’ll work in a remote-friendly environment with opportunities across 30+ states. The role emphasizes user-centric service, enrollment execution, and regulatory guidance during enrollment periods.

Qualifications

• Fast learner with interest in Medicare/Medicaid nationwide.
• Comfortable using AI tools for research, drafting and problem-solving.
• Ability to handle complex user inquiries and multitask.
• Clear communication and ability to explain concepts simply.
• Active pursuit of broker/agent health insurance licensure.
• Willingness to complete training and exams for carrier appointments.

Responsibilities

• Respond to inquiries about D-SNPs, Traditional Medicare, Medicare Advantage, and Medicaid via in-app chat and phone.
• Use AI tools to research plan details, compare options, and summarize regulations.
• Prioritize user needs and exceed service expectations.
• Compare Medicare Advantage plans and explain options based on user needs.
• Educate on eligibility, enrollment, and compliance requirements.
• Execute enrollment applications and inform users of deadlines.
• Maintain appointments with 30+ state carriers and ensure licensing compliance.
• Collaborate with product, design, and engineering to improve app features.
• Leverage AI to draft communications, summaries, and detect user inquiry patterns.
• Provide feedback to improve user and agent experiences.

Skills

Fast learner

AI tool proficient

Active listening

Complex issue handling

Licensing readiness

Excellent communication

Job description

About the Role

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.

What You’ll Do

• 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.

This Role Might Not Be the Right Fit If

We believe in being upfront so you can make the best decision for yourself. Propel is a startup, and our healthcare team is still building many of the processes and playbooks that larger organizations already have in place. That is exciting, but it is not for everyone, and that is completely okay.

This role may not be the right fit if:

• You prefer a structured environment with established workflows and detailed guidance for every situation. We are still writing the playbook here.
• You do best with consistent, close oversight before taking action. Our team operates with a high degree of autonomy and trust.
• You are looking for a role where the scope of your work is unlikely to change. We are growing fast, expanding into new states, and adapting constantly.
• You are not comfortable using technology or AI tools as part of your daily workflow. We are a tech company at our core, and our advisors work alongside AI every day.

Required Qualifications

• 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.

Preferred Qualifications

• Fluency in Spanish.
• Prior experience in healthcare, insurance, benefits counseling, or customer service roles.
• Experience working at a startup or tech company.

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.
• 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 believes that everyone should be compensated fairly and equitably. We set our salary ranges using compensation data from hundreds of NYC‑based startups at our stage. Additionally, pay is not determined based on location. Compensation for this position includes base salary and a performance‑based bonus. The expected base salary for the role is $70,000 - $80,000.

Additional Considerations

• We are committed to building a diverse and inclusive team, and welcome applicants from all backgrounds and abilities.
• Interview Accommodations: Propel is committed to providing reasonable accommodations throughout the interview process. If you need accommodations due to a disability or medical condition (such as additional time or accessibility support), please let us know as early as possible so we can support you appropriately.
• 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).