Full-Time

Medicare Sales Representative

Posted on 8/18/2026

Wider Circle

Wider Circle

51-200 employees

Community-based health and social engagement

Compensation Overview

$45k - $50k/yr

+ Performance-based incentive bonuses

Remote in USA

Hybrid

Travel throughout the organization's service area is required, including provider clinics in Los Angeles and Orange County.

Bachelor's

Category
Sales & Account Management (1)
Required Skills
Microsoft Office
Lead Generation
Forecasting
HubSpot
Word/Pages/Docs
Salesforce
Customer Service
Google Workspace

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Requirements
  • A minimum of two years of successful Medicare telesales, telemarketing, or customer service experience in a call center setting, with a background in Medicare products.
  • Ability to travel throughout the organization's service area.
  • Ability to work independently as a self-starter and as part of a team.
  • Effective verbal and written communication skills.
  • Proficiency with customer relationship management systems such as Salesforce and HubSpot, health plan portals, Google Workspace, and Microsoft Office, including Microsoft Word.
  • Must be a captive agent.
  • Current knowledge of Centers for Medicare & Medicaid Services regulations related to marketing, benefits, enrollment, and other regulatory guidelines.
  • A bachelor's degree in marketing, finance, or business administration.
  • Product and benefits training and/or other Centers for Medicare & Medicaid Services-required courses.
Responsibilities
  • Manage the prospective beneficiary cycle, including lead generation, relationship building, obtaining the Scope of Appointment, product presentation, sales conversion, and Medicare beneficiary relationship management.
  • Complete a predetermined daily goal of outbound calls to prospective beneficiaries to determine interest and eligibility and secure the Scope of Appointment.
  • Visit provider clinics in Los Angeles and Orange County to meet with beneficiaries.
  • Use a consultative sales approach to determine needs, present plans, handle obstacles, and close sales by phone or in person.
  • Educate prospective beneficiaries and complete the enrollment application process.
  • Answer product and service questions professionally and in a timely manner.
  • Develop sites and secure organizations for community and provider-based sales and marketing activities that create membership growth opportunities.
  • Attend daily and weekly team meetings to report production.
  • Maintain reports on business activities, productivity tracking, forecasting, and sales analysis.
  • Maintain strong familiarity with competitors and the overall market environment.
  • Perform related duties as assigned.

Wider Circle builds peer-led community care in local neighborhoods to improve health and reduce isolation. Members join a lifelong membership and participate in weekly health and social activities—bus tours, fitness classes, community gardens, and wellness workshops—organized through partnerships with healthcare providers and local organizations. Unlike traditional aging or disease-focused services, Wider Circle combines ongoing peer support with broad community activities and local partnerships to keep members engaged over time. Its goal is to boost health, independence, and social connections for older adults and others seeking better well-being.

Company Size

51-200

Company Stage

Series B

Total Funding

$38M

Headquarters

Redwood City, California

Founded

2015

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Simplify Jobs

Simplify's Take

What believers are saying

  • CalOptima Health granted Wider Circle a dual-eligible pathway across Orange County.
  • ApolloMed partnership extends ECM reach into high-need Medicaid populations in California.
  • Menda Health broadens clinical depth, strengthening Medicare Advantage and Medicaid sales.

What critics are saying

  • Integration of Menda Health risks distraction and churn through 2026.
  • California-heavy expansion leaves revenue exposed if CalOptima, CareFirst, or Highmark renewals slip.
  • If payers fail to see measurable savings, the community-care model loses contracts.

What makes Wider Circle unique

  • Peer-driven circles turn neighbors into care infrastructure, unlike episodic telehealth.
  • February 4, 2026 CalOptima partnership deepened Wider Circle’s eleventh California payer relationship.
  • May 19, 2026 Menda Health acquisition adds longitudinal virtual care for chronic pain.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

401(k) Retirement Plan

Paid Vacation

Employee Assistance Program

Health Care FSA

Dependent Care FSA

Health Savings Account

Voluntary Disability Benefits

Basic Life and AD&D Insurance

Adoption Assistance

Training Programs

Flexible Work Hours

Growth & Insights and Company News

Headcount

6 month growth

-1%

1 year growth

0%

2 year growth

0%
Wider Circle
May 19th, 2026
Wider Circle acquires Menda Health to expand group-based care for seniors with chronic pain

Wider Circle, a company focused on building communities to improve senior health, has acquired Menda Health, a virtual care provider for adults with chronic pain. The acquisition unites two organisations centred on group-based care models for seniors. Menda Health developed a group-based behavioural care model combining structured sessions with evidence-based approaches to help seniors manage chronic pain. The company was founded by Dr Les Aria, Arun Nijhawan and Kartik Shastri. Wider Circle's peer-driven model recruits community members to lead health engagement programmes for Medicare Advantage, Medicaid and dual-eligible members. The acquisition will enable Wider Circle to expand its longitudinal care capabilities. Financial terms of the deal were not disclosed.

Our Health Needs
Sep 24th, 2024
Wider Circle, CareFirst partner to establish peer-driven communities

In 2023, Wider Circle named Brett Zelkind chief strategy officer.

Hospitals Management
Nov 8th, 2023
ApolloMed and Wider Circle Enter Strategic Partnership to Elevate the Delivery of Patient-Centered Care for High-Need Community Members

Wider Circle, a peer-based community health organization working with payers and providers to connect neighbors for better health, today announced that it has entered into a strategic partnership with Apollo Medical Holdings, Inc. ("ApolloMed") (NASDAQ: AMEH), a technology-powered healthcare company empowering providers to deliver high-quality, value-based care to all in their community, to deliver Enhanced Care Management (ECM) to high-need Medicaid members across the state of California.

Wider Circle
Apr 10th, 2023
Wider Circle Expands Maternal Health Program Moms Connect for Life® for Historically Underserved Populations

Wider Circle introduces a peer-based community maternity program in Detroit, Michigan, to support expecting women through pregnancy into motherhood.

Wider Circle
Apr 5th, 2022
Wider Circle hired Claude Pinnock on Apr 5th 22'.

Wider Circle, a peer-based community health organization working with payers and providers to connect neighbors for better health, today announced the appointment of Claude Pinnock, MD MPH as chief medical officer.