Data Entry Remote Weekend Jobs in Wisconsin (NOW HIRING)

Are you a customer-focused professional who enjoys building relationships, solving problems, and helping individuals make informed decisions? We are seeking an Inside Sales Support Specialist to support Medicare membership growth by guiding prospective members through the initial enrollment process and connecting qualified individuals with licensed sales representatives.

This is an exciting opportunity to join a growing team where you can make a meaningful impact on members' healthcare decisions while earning performance incentives in a fully remote environment.

As an Inside Sales Support Specialist, you will be the first point of contact for prospective Medicare members. Through inbound and outbound calls, you will assess eligibility, answer questions, educate prospects on available options, and facilitate warm transfers to licensed sales representatives who will complete the enrollment process.

The ideal candidate is customer-focused, results-driven, organized, and comfortable working in a metrics-driven contact center environment.

• Conduct inbound and outbound calls with prospective Medicare members.
• Complete initial qualification and needs assessments with interested prospects.
• Educate potential members about the enrollment process and available Medicare plan options.
• Transfer qualified prospects to licensed sales representatives for plan recommendations and enrollment assistance.
• Deliver exceptional customer service while maintaining compliance with healthcare regulations and company policies.
• Accurately document customer interactions, inquiries, and outcomes within internal systems.
• Meet and exceed individual and team performance goals related to productivity, quality, and membership growth.
• Maintain a strong understanding of Medicare products, enrollment guidelines, and compliance requirements.
• Effectively manage multiple systems and tasks while maintaining attention to detail.
• Collaborate with team members and leadership to support overall sales and member experience goals.

• Bachelor's degree or an equivalent combination of education and experience.
• 1-3 years of experience in health plan sales, inside sales, insurance sales, broker support, or a related customer-facing role.
• Previous experience in a contact center or high-volume customer service environment.
• Experience handling inbound and outbound calls.
• Strong written and verbal communication skills.
• Excellent customer service and relationship-building abilities.
• Strong documentation and data entry skills.
• Ability to multitask and navigate multiple systems simultaneously.
• Strong problem-solving and organizational skills.
• Ability to prioritize workload and meet deadlines in a fast-paced environment.

• $21.50/hour
• +$1.00/hour shift differential for shifts ending at or after 6:30 PM
• Voluntary overtime opportunities available
• Team bonus eligibility ranging from $300-$500 during the contract period

Day Shift

• 8:00 AM - 5:00 PM CST

Evening Shift

• 11:30 AM - 8:00 PM CST

• Monday through Friday
• 8:00 AM - 4:30 PM CST

• Fully remote position
• Must reside within 30 miles of one of the following hub locations:
  • Minnetonka, MN
  • Madison, WI
  • Omaha, NE
  • St. Louis, MO
• Quiet, distraction-free home office required
• Optional onsite hoteling workspace available if preferred

• Fully remote work environment
• Competitive pay with shift differential opportunities
• Bonus and overtime earning potential
• Collaborative and supportive team culture
• Opportunity to gain valuable Medicare and health insurance industry experience
• Growth and development within a customer-focused sales organization
• Meaningful work helping individuals navigate important healthcare decisions

If you are energized by helping people, enjoy customer conversations, and thrive in a goal-oriented environment, we'd love to hear from you!

This is a Contract position based out of Madison, WI.

The pay range for this position is $21.50 - $22.50/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)

This is a fully remote position.

This position is anticipated to close on Aug 21, 2026.

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.

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.