Medicare Sales Representative

Posted 8/17/2026 · last confirmed live 8/26/2026

Join a fast-growing boutique insurance agency focused on helping people understand their Medicare Benefits. We work with underserved populations to help them navigate Medicare to identify the best benefits for their individual needs. Company Overview At Wider Circle, we connect neighbors for better health. Wider Circle's groundbreaking Connect for Life® program brings neighbors together in-person and online for health, wellness, and social activities that improve mental and physical health. We create webs of community circles by employing local and culturally competent engagement specialists, whose hand-on-hand approach to forming trusted circles is informed by a sophisticated analytics platform. We are on a mission to make the world a better place for older adults and disadvantaged communities. Wider Circle works with health plans and providers nationally to deliver unique community care programs that connect neighbors for better health. Centered on trusted relationships, Wider Circle connects health plan members with like-minded neighbors to inform, support and motivate one another, empowering them to be more proactive about their health. Wider Circle’s trusted delivery network has been proven to drive resilience, improve member experience and engagement, and reduce inappropriate utilization and has been published in peer-reviewed literature. Today, Wider Circle offers its unique neighborhood care programs to tens of thousands of communities nationwide. To learn more, visit widercircle.com. Responsibilities Primarily be responsible for the entire prospective beneficiary cycle that includes but is not limited to lead generation, relationship building, obtaining the Scope of Appointment, the presentation of the product, sales conversion, and relationship management of a Medicare beneficiary. Daily tasks include completing a predetermined goal of outbound calls each day to prospective beneficiaries to determine interest and eligibility and to secure the Scope of Appointment. Visit provider clinics in Los Angeles and Orange County to meet with beneficiaries. Utilize a consultative sales approach to determine needs, make plan presentations, handle obstacles, and close the sale over the phone or in person. Interacts with prospective beneficiaries through education and complete enrollment application process Answer product and service questions in a professional and timely manner Perform various related duties as assigned Develop sites and secure organizations for community and provider-based sales and marketing activities that provide membership growth opportunities. Attend daily and weekly team meetings to report production Provides and maintains reports on business activities, productivity tracking, forecasting, and sales analysis Maintains strong familiarity with competitors and the overall market environment Requirements Minimum two (2) years of successful Medicare telesales, telemarketing, or customer service experience in a call center setting with a background in Medicare products Applicant must be able to travel throughout the organization's service area. Ability to work as an independent self-starter part of a team Proficiency in effective verbal and written communication skills Effective computer and application knowledge of Client Relationship Management systems like Salesforce, Hubspot, Health plan portals, Google Workspace, and Microsoft Office suite Microsoft Word Be a captive agent Current knowledge of CMS regulations related to marketing, benefits, enrollment, and other guidelines as governed by regulatory agencies Bachelor's degree in marketing, finance, and business administration Product and Benefits training and/or other CMS-required courses Benefits As a venture-backed company, Wider Circle offers competitive compensation including: Performance-based incentive bonuses Opportunity to grow with the company Comprehensive health coverage including medical, dental, and vision 401(k) Plan Paid Time Off Employee Assistance Program Health Care FSA Dependent Care FSA Health Savings Account Voluntary Disability Benefits Basic Life and AD&D Insurance Adoption Assistance Program Training and Development Starting salary: $45,000-$50,000 And most importantly, an opportunity to LOVE, LEARN and GROW with us! Wider Circle is proud to be an equal-opportunity employer that does not tolerate discrimination or harassment of any kind. Our commitment to Diversity & Inclusion supports our ability to build diverse teams and develop inclusive work environments. We believe in empowering people and valuing their differences. We are committed to equal employment opportunity without consideration of race, color, religion, ethnicity, citizenship, political activity or affiliation, marital status, age, national origin, ancestry, disability, veteran status, sexual orientation, gender identity, gender expression, sex or gender, or any other basis protected by law.

This role is published by Wider Circle on workable. SwiftFit is not the employer and does not accept applications.