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Medicare Sales Representative

Connie Health, Boston, MA, United States


Connie Health is a fast‑growing Medicare brokerage on a mission to empower older Americans to make confident, worry‑free Medicare plan decisions. We offer a tech‑enabled Medicare navigation platform that combines an

AI‑driven technology

with local Medicare experts to help people select optimal healthcare plans and navigate their benefits.

Role Overview As a

Medicare Sales Representative , you will assist customers—primarily via phone—in selecting and enrolling in health insurance plans. Your responsibilities include handling inbound calls, providing product information, answering questions, guiding customers through enrollment, meeting sales targets, adhering to compliance standards, and delivering a positive customer experience.

What You’ll Do

Serve as a trusted advisor to Medicare beneficiaries, helping them confidently navigate their insurance options

Conduct in-depth needs assessments via phone to understand each client’s healthcare and coverage requirements

Educate clients on Medicare options, election periods, and available services to help them make informed decisions

Match beneficiaries with the most suitable health plans based on their unique needs

Guide clients through the enrollment process with care, accuracy, and personalized support

Build meaningful relationships while delivering excellent, solutions‑focused customer service

Qualify inbound leads and create new sales opportunities through proactive engagement

Consistently meet or exceed sales goals while tracking performance and progress

Stay current on CMS regulations, HIPAA policies, and Medicare compliance requirements

Accurately document all sales and service activities in the CRM system

Collaborate with managers, trainers, and team members to refine skills and achieve individual and team goals

Support additional duties and special projects as needed

What You Bring

2–3 years of Medicare sales experience

Active Health & Life Insurance License

Current AHIP certification

Strong technical skills and comfort using multiple systems (iOS, Salesforce, Five9, Slack preferred)

Excellent verbal and written communication skills

Bilingual a plus

Why Join Connie Health?

Generous vacation policy and paid holidays

Comprehensive health insurance coverage

401(k) with company match

A collaborative, mission‑driven, and innovative culture

Remote work flexibility and growth opportunities

We are proud to be an Equal Opportunity Employer and are committed to building a diverse and inclusive team. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, gender identity, sexual orientation, national origin, disability, or veteran status.

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