Apply Now Please mention DailyRemote when applying

Disclaimer: Before you apply, please make sure the job is legit.

Attempting to apply for jobs might take you off this site to a different website not owned by us. Any consequence as a result for attempting to apply for jobs is strictly at your own risk and we assume no liability.

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.



  • 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.
  • Bi-lingual in Spanish, Khmer, Creole, Mandarin, Arabic, or other languages 
  • 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, with the ability to 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, bachelor degree 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
  • Training and Development
  • Contract/1099
  • $15-$17 hr

And most importantly, an opportunity to make the world a better place!

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. 

Ace Your Job Interview

Read our advice on how to answer the most common interview questions.