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Medicare & Health Insurance Outbound Appointment Setting Virtual Assistant

Jobgether
Contract type
Freelance
Work mode
Remote
Experience
3 years

Listing closes 10 Nov 2026

Job description

Outbound appointment-setting role calling Medicare leads to schedule appointments with licensed insurance representatives. It is a fully remote independent contractor engagement of about 20 hours per week.

At a glance

Employment
Part-time · Independent contractor
Work mode
Remote
Languages
English – fluent

What you'll do

  • Conduct outbound calls to existing, previous, and new Medicare leads using client-provided contact lists
  • Introduce the purpose of each call using approved scripts and determine whether individuals are interested in discussing their Medicare coverage with a licensed insurance representative
  • Ask appropriate follow-up questions, identify appointment preferences, address routine objections within established guidelines, and schedule qualified appointments
  • Communicate with seniors using patience, empathy, and clear language, adjusting the pace of conversations and clarifying information when necessary
  • Follow up with interested prospects who have not yet scheduled appointments and maintain continuity throughout the outreach process
  • Document questions, objections, concerns, and requests requiring additional attention from the agency
  • Refer questions about Medicare plans, prescription coverage, eligibility, and insurance benefits to authorized representatives rather than providing unapproved advice
  • Direct Spanish-language inquiries to the designated bilingual team member
  • Record call outcomes, contact details, appointment dates, follow-up requests, and other relevant information in Microsoft Excel and the client's designated systems
  • Maintain accurate, organized lead-tracking spreadsheets and monitor outstanding callbacks and unresolved inquiries
  • Submit completed call records and appointment information and prepare daily end-of-day reports summarizing call activity, appointments scheduled, and pending tasks
  • Support seasonal Medicare outreach campaigns during applicable enrollment periods and learn additional approved scripts for future health insurance initiatives
  • Assist with Covered California appointment-setting campaigns as trained and maintain accurate records when transitioning between outreach campaigns
  • Use the client's phone and VoIP systems, email and calendar platforms, lead-tracking tools, and appointment scheduling software to complete assigned tasks
  • Follow documented procedures, agreed service timelines, quality standards, and the terms of the independent contractor engagement

What we're looking for

  • Previous experience in phone-based customer service, outbound calling, telemarketing, or a similar client-facing role is required
  • Excellent spoken and written English, with a clear, professional, and easily understood speaking style
  • Strong listening, patience, empathy, rapport-building, and conversational communication skills
  • Ability to follow established scripts while maintaining natural, respectful conversations and handling routine objections professionally
  • Strong organizational skills and attention to detail when recording contact information, call outcomes, appointments, and follow-up requirements
  • Practical proficiency in Microsoft Excel, including accurate data entry and maintaining structured tracking worksheets
  • Ability to learn new scripts, follow campaign-specific procedures, and adapt to changing enrollment periods and outreach priorities
  • Willingness to learn and use Ooma or comparable phone systems, VoIP communication platforms, email and calendar tools, and lead management or appointment scheduling software
  • Dependability, consistency, coachability, and the ability to manage outbound calling responsibilities independently
  • Access to reliable high-speed internet, suitable computer equipment, and a quiet home-based workspace
  • Availability to work Monday through Friday, 10:00 AM–2:00 PM Pacific Standard Time (PST), for approximately 20 hours per week
  • Ability to work as an independent contractor under a Master Services Agreement and Statement of Work
  • Applicants based in Australia should ensure they can consistently accommodate the required U.S. Pacific working hours

Nice to have

  • A native or near-native English accent is preferred
  • Experience setting appointments is strongly preferred, particularly in lead generation, customer outreach, or sales support
  • Experience communicating with seniors or other individuals who may need additional time, clarification, or reassurance is an advantage
  • Familiarity with Medicare, health insurance, healthcare services, or insurance-related customer support is preferred
  • Offshore or nearshore candidates are preferred

Benefits

Opportunity to develop experience in healthcare-related customer service, outbound appointment setting, lead management, and administrative support

  • Fully remote independent contractor opportunity
  • Approximately 20 contracted hours per week, with the possibility of additional hours based on performance and workload
  • Competitive contractor rates; specific compensation figures are not provided in the source listing
  • Weekly payments according to the engagement terms
  • Free training and opportunities for professional upskilling
  • Ongoing support, guidance, and assistance with learning client-specific tools and procedures
  • Access to a supportive professional community
  • Potential to support additional health insurance outreach campaigns as business needs evolve
  • Compensation is processed through the contracting service provider in accordance with the applicable agreement

How to get hired

  1. 1AI-powered matching process reviews applications against the role's core requirements
  2. 2Shortlist shared directly with the hiring company
  3. 3Final decision and next steps (interviews, assessments) managed by the hiring company's internal team

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About Jobgether

Key facts

  • Uses an AI-powered matching process to review applications quickly, objectively, and fairly against the role's core requirements
  • Identifies top-fitting candidates and shares the shortlist directly with the hiring company