Medicare & Health Insurance Outbound Appointment Setting Virtual Assistant

Jobgether; Italia; Remote; EUR 15,000 - 25,000; Part time

Benefits offered by this job

Fully remote

Weekly payments

Free training

Ongoing support

Healthcare experience growth

Job summary

Jobgether is seeking a remote Medicare & Health Insurance Outreach Assistant based in Italy. This independent contractor role supports a U.S.

health insurance agency with outbound calling, appointment scheduling, and lead management. You will engage with Medicare clients, use approved scripts, and schedule appointments with licensed representatives while documenting inquiries and maintaining accurate records.

Qualifications

• Experience in phone-based customer service or telemarketing is required.
• Excellent spoken and written English with a clear, professional style.
• Experience setting appointments in lead generation, outreach, or sales support is preferred.
• Experience communicating with seniors or those needing time and reassurance is advantageous.
• Strong listening, patience, empathy, and conversational skills are essential.
• Ability to follow scripts while maintaining natural conversations and handling objections.
• Strong organizational skills and attention to detail in recording information.
• Familiarity with Medicare/health insurance support is preferred.

Responsibilities

• Conduct outbound calls to Medicare leads using client-provided lists.
• Use approved scripts to determine interest in discussing Medicare coverage.
• Schedule qualified appointments and address routine objections.
• Communicate with seniors with patience, empathy, and clear language.
• Document questions, concerns, and follow-up requirements in tracking tools.
• Record call outcomes and appointment details in Excel and other systems.
• Prepare daily end-of-day reports summarizing activity and outcomes.
• Support campaigns during enrollment periods and learn new scripts as needed.
• Use VoIP systems and scheduling software to complete tasks.

Skills

Outbound calling

Customer service

English proficiency

Appointment setting

Active listening

Organizational skills

Data entry

Tech familiarity

Tools

Microsoft Excel

VoIP systems

Appointment scheduling software

Lead management software

Job description

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Medicare & Health Insurance Outbound Appointment Setting Virtual Assistant based in Italy.

This remote independent contractor opportunity involves supporting a U.S.-based health insurance agency with outbound calling, appointment scheduling, and lead management. You will connect with existing and prospective Medicare clients, introduce insurance consultations using approved scripts, and schedule appointments with licensed insurance representatives. A key part of the role is communicating with older adults in a patient, empathetic, and reassuring manner while ensuring their questions and concerns are properly documented. You will also maintain accurate lead records, track follow-ups, and provide daily activity reports to support efficient operations. As enrollment periods and campaign priorities change, you may contribute to additional health insurance outreach initiatives. This position is well suited to a confident communicator who enjoys helping people, is comfortable with phone-based work, and can combine excellent customer service with organized administrative support.

Accountabilities

• 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.

Requirements:

• 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. 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.

• 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.

• Familiarity with Medicare, health insurance, healthcare services, or insurance‑related customer support is preferred.

• 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. Training on the client’s system will be provided as needed.

• 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. Hours may increase depending on performance and workload, subject to mutual agreement.

• Ability to work as an independent contractor under a Master Services Agreement and Statement of Work. This opportunity is not an employment position, and contractors are not employees of the client or the service provider.

• Offshore or nearshore candidates are preferred. Applicants based in Australia should ensure they can consistently accommodate the required U.S. Pacific working hours.

Benefits:

• 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.

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

• 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.

• Healthcare coverage, paid leave, retirement benefits, and other employee benefits are not specified. As this is an independent contractor engagement, employment benefits should not be assumed.

How Jobgether works:

We use an AI‑powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role’s core requirements. Our system identifies the top‑fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre‑contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.