Question
2-5

Medicare Sales Representative

2/6/2026

As a Medicare Sales Representative, you will assist customers in selecting and enrolling in health insurance plans primarily via phone. You will conduct needs assessments, educate clients on Medicare options, and guide them through the enrollment process.

Working Hours

40 hours/week

Company Size

11-50 employees

Language

English

Visa Sponsorship

No

About The Company
Connie Health empowers older Americans to make confident, worry-free healthcare decisions. Our Medicare consumer platform combines a tech-driven recommendation engine with local agents for personalized plan and healthcare navigation. We help consumers find the Medicare plan that meets their individual health and economic needs, take advantage of the benefits covered by that plan, and find the best providers in network. Headquartered in Boston, MA. Currently helping older Americans in Arizona, Texas and Chicago. #medicareinsurance #medicareadvantage #medicaresupplement
About the Role

Description

About Connie Health

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. Our culture is mission-driven, collaborative, and innovative, as we strive to transform healthcare through data-driven insights and personalized guidance. We value Relationships First, Data-Driven decision making, and being Accountable in delivering unbiased, high-quality advice to our members.


At Connie Health, we’re revolutionizing the way older Americans navigate Medicare.As we expand into new and existing markets, we’re seeking a Medicare Sales Representative.


Role Overview


As a Medicare Sales Representative, you will be assisting customers, primarily via phone, in selecting and enrolling in health insurance plans. This role may include handling inbound calls, providing product information, answering questions, and guiding customers through the enrollment process. You will be responsible for meeting sales targets, adhering to compliance standards, and providing 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


Requirements

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.


Key Skills
Medicare SalesHealth InsuranceCustomer ServiceCommunication SkillsTechnical SkillsCompliance KnowledgeCRM DocumentationBilingual
Categories
HealthcareSalesCustomer Service & Support
Benefits
Generous Vacation PolicyPaid HolidaysComprehensive Health Insurance Coverage401(k) With Company Match
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