REMOTE Insurance Sales Representative

Remote Medicare Sales RepresentativePosition Overview

We are seeking motivated and customer-focused Medicare Sales Representatives to join a growing remote sales team. In this role, you will educate prospective and current Medicare members on available health plan options, benefits, and enrollment requirements while delivering an exceptional customer experience. The ideal candidate will have experience in Medicare Advantage sales, health insurance products, and telephonic member engagement.

Work Schedule:

Monday–Friday between 8:00 AM and 5:30 PM, with occasional weekend coverage as needed.

Work Arrangement:

100% Remote

Key Responsibilities

• Conduct telephonic sales presentations and assist eligible members with Medicare plan enrollments in accordance with CMS regulations and compliance requirements.

• Educate prospective and current members on Medicare products, benefits, coverage options, enrollment guidelines, and next steps.

• Assess customer needs and recommend appropriate Medicare plans based on eligibility and coverage requirements.

• Accurately document member interactions, enrollment activities, and follow-up actions within designated systems and platforms.

• Maintain up-to-date knowledge of Medicare products, benefits, enrollment policies, scripts, and regulatory changes.

• Deliver outstanding customer service through active listening, professionalism, empathy, and timely follow-up.

• Collaborate with cross-functional teams to address member concerns, improve processes, and ensure a positive member experience.

• Meet established productivity, quality, compliance, and customer satisfaction goals.

• Participate in special projects and additional duties as assigned.

Required Qualifications

• Active Health Insurance License required.

• Ability to obtain and maintain a New York insurance appointment within 30 days of hire.

• AHIP certification or experience working with AHIP-compliant Medicare sales practices.

• Working knowledge of Medicare products, Medicare Advantage plans, CMS regulations, enrollment guidelines, and compliant sales practices.

• 2+ years of experience in sales, telesales, customer service, call centre, or member services, preferably within healthcare or insurance.

• Strong verbal and written communication skills with the ability to explain complex information in a clear, customer-friendly manner.

• Experience handling high call volumes while maintaining accuracy, professionalism, and service quality.

• Proficiency with Microsoft Office and experience using CRM systems, enrolment platforms, or related software.

• Strong organisational, analytical, problem-solving, and time-management skills.

• Ability to maintain confidentiality and handle sensitive member information appropriately.

Preferred Qualifications

• Experience selling Medicare Advantage or health insurance products.

• Previous experience in health benefits, insurance enrolment, member services, or healthcare sales.

• Knowledge of claims, billing, customer service, or health plan administration.

• Bilingual Spanish language skills.

• Additional experience may be considered in lieu of a degree.

Ideal Candidate

The successful candidate will be a results-driven sales professional who is passionate about helping individuals understand their healthcare coverage options. They will possess strong customer service skills, a solid understanding of Medicare products, and the ability to build trust and rapport with members over the phone while maintaining strict compliance standards.

Job Type & Location

This is a Contract position based out of Chicago, IL.

Pay and Benefits

The pay range for this position is $25.00 - $25.00/hr.

Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following: • Medical, dental & vision • Critical Illness, Accident, and Hospital • 401(k) Retirement Plan – Pre-tax and Roth post-tax contributions available • Life Insurance (Voluntary Life & AD&D for the employee and dependents) • Short and long-term disability • Health Spending Account (HSA) • Transportation benefits • Employee Assistance Program • Time Off/Leave (PTO, Vacation or Sick Leave)

Workplace Type

This is a fully remote position.

Application Deadline

This position is anticipated to close on Jul 29, 2026.

About TEKsystems

We're partners in transformation. We help clients activate ideas and solutions to take advantage of a new world of opportunity. We are a team of 80,000 strong, working with over 6,000 clients, including 80% of the Fortune 500, across North America, Europe and Asia. As an industry leader in Full-Stack Technology Services, Talent Services, and real-world application, we work with progressive leaders to drive change. That's the power of true partnership. TEKsystems is an Allegis Group company.

The company is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

About TEKsystems and TEKsystems Global Services

We’re a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. We’re a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. We’re strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. We’re building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Massachusetts Lie Detector: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.