[Hiring] Medicare & Health Insurance Outbound Appointment Setting Virtual Assistant @20four7VA

Role Description

20four7VA is seeking offshore independent contractors to deliver remote services to clients worldwide, with a primary focus on developed markets such as the United States, the United Kingdom, Canada, and Australia. A California-based Medicare and health insurance agency is seeking a compassionate and confident Business Support VA to handle outbound prospect calling, enrollment-period outreach, appointment scheduling, and lead tracking.

The VA will initially contact existing and new Medicare leads during the Annual Enrollment Period, using established scripts to determine interest, handle routine questions, and schedule appointments with licensed insurance representatives. The ideal candidate will bring excellent spoken English, patience, empathy, and strong listening skills, particularly when communicating with seniors who may require additional time or clarification.

The objective of each engagement is to assist the client in improving business efficiency, enhancing service delivery, or supporting operational functions through high-quality, task-specific services rendered by a qualified contractor.

Scope of Services

• Outbound Calling & Appointment Setting
  • Contact existing, previous, and new Medicare leads using provided lists
  • Explain the purpose of outreach using approved scripts
  • Determine whether individuals are interested in discussing Medicare coverage with the agency
  • Ask appropriate questions to clarify interest and appointment preferences
  • Handle routine objections and questions within established guidelines
  • Schedule appointments with licensed insurance representatives
• Senior-Focused Communication & Follow-Up
  • Maintain patient, respectful, and empathetic conversations with seniors
  • Adjust communication pace and clarify questions when needed
  • Follow up with interested individuals who have not yet scheduled appointments
  • Document questions, objections, and concerns requiring follow-up by the agency
  • Direct Medicare plan, prescription, eligibility, and coverage questions to authorized representatives
  • Route Spanish-language inquiries to the designated bilingual team member
  • Maintain a professional, reassuring, and conversational phone presence
• Excel Tracking & Administrative Support
  • Record call outcomes, dispositions, and contact information in Excel
  • Document names, phone numbers, appointment dates, and requested follow-ups
  • Maintain accurate and organized lead-tracking worksheets
  • Submit completed call records and appointment information to client
  • Track outstanding callbacks and unresolved questions
  • Provide daily end-of-day reports on calling activity, appointments, and outstanding items
• Seasonal Insurance Outreach Support
  • Support Medicare outreach during applicable enrollment periods
  • Learn additional approved scripts for future health insurance campaigns
  • Assist with Covered California appointment-setting outreach as trained
  • Maintain accurate records and follow-up continuity when transitioning between campaigns

Qualifications

• Strong phone-based customer service or outbound calling experience required
• Excellent spoken and written English required
• Appointment-setting experience strongly preferred
• Experience communicating with seniors a plus
• Ability to follow scripts and handle routine objections required
• Strong listening, patience, and rapport-building skills required
• Microsoft Excel and accurate data-entry experience required
• Medicare, insurance, or healthcare-industry familiarity preferred
• Ability to learn additional insurance outreach scripts preferred

Benefits

• Competitive rates
• Weekly payments
• Various open roles are available
• Free training and upskilling
• Constant support and guidance
• A vibrant community always ready to support you
• And more!

Work Schedule

• Contracted Hours per Week: 20 Hours (Hours may increase based on performance and workload)
• Scheduled Working Days: Monday through Friday (unless otherwise mutually agreed in writing)
• Daily Working Time: 10:00 AM–2:00 PM PST

Terms of Engagement

• Contractors will operate under a Master Services Agreement and a Statement of Work
• This is not an offer of employment; contractors are not employees of 20four7VA or any client
• All compensation is processed through 20four7VA according to the terms of the engagement