Medicare Advisor (AI)

Location: Remote within the United States; applications are currently accepted from California, Colorado, District of Columbia, Florida, Georgia, Illinois, Maryland, Massachusetts, New Jersey, New York, Oregon, Pennsylvania, Texas, Virginia, and Washington. Optional in-person retreats are held at the dog-friendly Downtown Brooklyn office.

Salary: $70,000–$80,000 base salary annually, plus a performance-based bonus.

Company

hirify.global is a venture-backed technology company building app-based tools that improve how government benefits are delivered to more than 5 million Americans.

What you will do

• Respond to user inquiries about D-SNPs, Traditional Medicare, Medicare Advantage, and Medicaid through in-app chat and phone.
• Research and compare healthcare plans, explain eligibility and enrollment requirements, and help users select coverage suited to their needs.
• Complete enrollment applications accurately and communicate deadlines and ongoing actions required to maintain coverage.
• Use AI tools to research plans, summarize regulatory information, draft communications, and identify patterns in user inquiries.
• Maintain appointments with insurance carriers across more than 30 states and comply with licensing requirements.
• Collaborate with product, design, and engineering teams to improve app functionality and enrollment workflows.

Requirements

• Fast learner with a strong interest in developing nationwide Medicare and Medicaid expertise.
• Comfortable using AI tools such as ChatGPT or Claude for research, drafting, and problem-solving.
• Ability to handle complex inquiries, multitask, actively listen, and explain complicated concepts clearly.
• Have or be willing to obtain an active health insurance broker or agent license in the home state and additional company-sponsored non-resident licenses.
• Willingness to complete training and carrier appointment tests.
• Must be able to work phone and chat shifts, including approximately one weekend day per week, during the October 15–December 7 Annual Enrollment Period, and must refrain from vacation during this period.

Nice to have

• Fluency in Spanish.
• Experience in healthcare, insurance, benefits counseling, or customer service.
• Experience working at a startup or technology company.

Culture & Benefits

• Meaningful work focused on strengthening the social safety net.
• Remote-friendly work environment with optional in-person retreats.
• 20 days of PTO.
• 4% 401(k) match.
• $10,000 lifetime Carrot Fertility benefit.
• Medical, dental, vision, mental health, and other health-focused benefits.

Hiring process

• Background check may be conducted following a conditional offer.
• Reasonable interview accommodations are available for candidates who need accessibility or medical support.