Medicare Sales - Outreach Liaison

Wider Circle· Growth
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🌍 Remote📍 TELECOMMUTE📍 Texas, United StatesContract

About this role

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 needs. Ask Claire is looking for a remote telephonic Outreach Specialist to join our fast-paced team to connect with Medicare beneficiaries and help them schedule appointments with our licensed Medicare agents. The successful candidate will use their unique skills to build trust and establish rapport through genuine conversations, leading to successful appointments being scheduled with our licensed Medicare agents. They will maintain high productivity, discipline, and conversion rates to best support Medicare beneficiaries. If you are passionate about serving underserved populations and love building relationships over the phone, then come join us in our movement to support the Medicare population.

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.

Responsibilities

  • Daily tasks include completing a predetermined goal of outbound calls each day from the lead list to prospective beneficiaries to educate them about the additional benefits that are available to them, to secure the Scope of Appointment, and to schedule the plan presentation with a licensed Medicare agent.
  • You will maintain a consistent level of productivity, enthusiasm, and energy while making daily outbound calls.
  • You will master the details of outreach workflows and scripts while developing a conversational style that highlights your personality and connection to beneficiaries.
  • You will effectively engage with members during calls, probing to determine their needs and anticipate objections.
  • Attend daily and  weekly team meetings and be accountable for your output
  • Provide and maintain daily tasks related to call follow-ups, appointment scheduling, and productivity tracking
  • You will go the "extra mile" to meet the quota.
  • You will maintain a positive, professional attitude when interacting with internal and external customers.

  • Minimum two (2) years of successful Medicare telesales, telemarketing, or customer service experience in a call center setting with a background in Medicare products.
  • You are a self-starter, accountable, and have proven experience successfully meeting quotas in a telesales or call center role. 
  • You can work independently, maintaining a consistent work ethic in a remote work environment.
  • You have excellent communication, critical thinking, and interpersonal skills.
  • You have a good memory and can effortlessly explain our services to beneficiaries.
  • You have an outgoing personality and unwavering, positive attitude. You can comfortably engage with others while driving conversations forward. 
  • You have a flexible schedule, with the ability to work a set, recurring 40-hour schedule, with occasional work outside of regular business hours when necessary.
  • Effective computer and application knowledge of Client Relationship Management systems like Salesforce, multi-dialer phone system, Google Workspace, and Microsoft Office suite Microsoft Word is required
  • You are committed to a drug-free workplace and ready for pre-employment substance abuse testing and background checks.
  • Strong communication and customer service skills
  • Ability to track/monitor/retrieve information on calls
  • High school diploma or equivalent, degree preferred
  • Bilingual in Spanish, Khmer, Creole, Mandarin, Arabic, or other languages preferred

Join Wider Circle in our mission to build healthier and more connected communities.

Apply today to Learn, Love, and Grow with us!

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: $17.00-$18.00

And most importantly, an opportunity to LOVE, LEARN and GROW with us!

As a wholly owned subsidiary of Wider Circle, Ask Claire is uniquely positioned to promote

Wider Circle’s flagship wellbeing program, Connect for Life® to eligible individuals aging into

Medicare. Wider Circle is a neighborhood-based health organization that empowers members of

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. 

Frequently Asked Questions

Is the salary disclosed for the Medicare Sales - Outreach Liaison position at Wider Circle?
The salary for this Medicare Sales - Outreach Liaison role at Wider Circle is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Is the Medicare Sales - Outreach Liaison job at Wider Circle remote?
Yes, this Medicare Sales - Outreach Liaison position at Wider Circle is remote, with team members based in TELECOMMUTE, Texas, United States. You can work from home or anywhere in the supported regions.
Is the Medicare Sales - Outreach Liaison role at Wider Circle full-time or part-time?
This is listed as a Contract position. It is posted as a Medicare Sales - Outreach Liaison role in the Growth department at Wider Circle.
Which team or department does the Medicare Sales - Outreach Liaison at Wider Circle belong to?
This Medicare Sales - Outreach Liaison position is part of the Growth department at Wider Circle. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Medicare Sales - Outreach Liaison position at Wider Circle?
Click the "Apply Now" button on this page. You will be redirected to Wider Circle's official application portal hosted on workable where you can submit your application directly.
When was the Medicare Sales - Outreach Liaison job at Wider Circle posted?
This Medicare Sales - Outreach Liaison position at Wider Circle was posted on Aug 18, 2026. Apply as soon as possible — early applications are often reviewed first.
Medicare Sales - Outreach Liaison
Wider Circle
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You'll be redirected to Wider Circle's official application page on workable.