Two Chicks With A Side Hustle

Help underserved communities understand and access their Medicare benefits while working from home.

About Wider Circle / Ask Claire
Wider Circle is on a mission to connect neighbors for better health. Through our groundbreaking Connect for Life® program, we bring older adults and underserved communities together in-person and online for wellness and social activities that improve physical and mental health. As a wholly owned subsidiary of Wider Circle, Ask Claire focuses on helping Medicare beneficiaries identify the best benefits for their needs—especially those in underserved populations.

Schedule

  • Remote position (Los Angeles, CA candidates preferred)
  • Full-time, 40 hours per week with occasional work outside regular business hours
  • Contract role with potential growth opportunities
  • Must attend daily and weekly virtual team meetings

Responsibilities

  • Make high-volume outbound calls from a provided lead list to educate Medicare beneficiaries on available benefits
  • Secure Scope of Appointment and schedule plan presentations with licensed Medicare agents
  • Follow outreach scripts while adapting to a conversational style that builds trust and rapport
  • Probe to determine needs, address objections, and drive successful appointment bookings
  • Track productivity, appointment scheduling, and follow-ups in CRM systems (Salesforce)
  • Maintain professionalism and enthusiasm throughout calls
  • Meet or exceed daily and weekly performance quotas

Requirements

  • Minimum 2 years’ experience in Medicare telesales, telemarketing, or call center customer service
  • Bilingual in Spanish, Khmer, Creole, Mandarin, Arabic, or other languages
  • Proven success meeting quotas in a remote telesales role
  • Strong communication, interpersonal, and critical thinking skills
  • Ability to work independently in a remote setting with consistent productivity
  • Proficient in Salesforce, multi-dialer phone systems, Google Workspace, and Microsoft Office
  • High school diploma or equivalent (Bachelor’s degree preferred)
  • Must pass pre-employment drug screening and background check

Benefits

  • $15.00–$17.00/hour plus performance-based bonuses
  • Comprehensive medical, dental, and vision coverage
  • 401(k) plan
  • Paid Time Off (PTO)
  • Employee Assistance Program
  • Health Care and Dependent Care FSAs
  • Health Savings Account
  • Voluntary disability benefits
  • Basic life and AD&D insurance
  • Adoption assistance program
  • Training and development opportunities
  • Career growth potential within the organization

Make an impact while helping Medicare beneficiaries get the care they deserve—apply today!

Happy Hunting,
~Two Chicks…

APPLY HERE