Job Description
APPLICATION INSTRUCTIONS: If you’ve already completed the 20four7VA Recruiting Process—including the Final Interview—or have previously been contracted by a 20four7VA Client, please make sure to apply via the 20four7VA Team Portal for faster processing.
Log in using your 20four7VA-issued email address to access the portal.
If you’ve just logged in to the Team Portal, please proceed to review the Independent Contractor Opportunity outlined below.
💡 Quick Tip: Upload your resume first—this will automatically populate most of the fields in the application form. Let the magic happen!
If you’re interested in this opportunity, click APPLY TO POSITION to proceed.
\*\*\******************************************************************
Title: CPT-11661 Medicare & Health Insurance Outbound Appointment Setting Virtual Assistant
Independent Contractor – CPT-11661 Medicare & Health Insurance Outbound Appointment Setting Virtual Assistant/Business Support VA/Entry-Senior Level (Remote).
Overview
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 position may expand into other health insurance outreach campaigns as enrollment periods change.
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
Contractors will be required to provide services that align with the following client tasks:
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
Each engagement is based on a defined scope of work and is governed by an independent contractor agreement. Services must be performed professionally, with adherence to any timelines, guidelines, and deliverables agreed upon in writing.
Skills
The Contractor must demonstrate proficiency in the following, depending on the Client’s requirements:
- 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
IDEAL CANDIDATE PROFILE
- Warm, compassionate, and highly patient
- Confident and easy to understand over the phone
- Excellent listener who can ask thoughtful follow-up questions
- Comfortable speaking with older adults
- Able to follow scripts while maintaining natural conversations
- Organized and accurate with recordkeeping
- Dependable and consistent with outbound calling responsibilities
- Coachable and comfortable learning different insurance outreach procedures
APPLICATION SOFTWARE KNOWLEDGEABLE / REQUIRED
- Microsoft Excel
- Ooma – Client System; Training will be provided as needed
- Phone / VoIP Communication Platforms
- Email & Calendar Platforms
- Lead Tracking / Appointment Scheduling Tools
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
Note: The Company will make reasonable efforts to align the Assigned VA’s schedule with the Client’s preferred hours as set forth above. However, availability may vary based on time zones, capacity, and the contracted hours set in this SOW. Any changes must be mutually agreed to in writing through a revised SOW.
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
Role Summary & Requirements
- REQUIRED SERVICE: Business Support
- REQUESTED EXPERIENCE TIER LEVEL: Entry, Junior, Senior Level
- Contracted Hours per Week: 20 hours/week ( Hours may increase based on performance and workload)
- Daily Working Time: 10:00 AM–2:00 PM PST
- Scheduled Working Days: Monday-Friday
- REPORTING TO/POC: To Be Determined
- Number of VAs: 1
- GENDER PREFERENCE: Female
- LANGUAGES SPOKEN/PREFERENCE: English
- ACCENT PREFERENCE: Level A-B (Native or near-native English accent required)
- REGION PREFERENCES: Offshore or Nearshore
What we offer
- 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!
