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Remote Chat Agent Jobs in Milwaukee, WI (NOW HIRING)

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Medicare Customer Advisor Licensed Insurance Agent

Milwaukee, WI · On-site

$39K - $54K/yr

  • Medical

  • Dental

  • PTO

... remote team assisting Medicare customers during the Annual Enrollment Period. The selected candidates will communicate with customers by telephone and online chat, answer questions about Medicare ...

New

The Long Agency

Life Insurance Sales Agent

Milwaukee, WI · On-site +1

$30K - $160K/yr

As a Life Insurance Sales Agent with the Long Agency, you will work with individuals and families who have requested information about life insurance coverage. This is a consultative sales role ...

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TEKsystems

Customer Service Representative

Milwaukee, WI · Remote

$19 - $20/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

... phone, chat or case workload in accordance with schedule, standards and volumes adhering to ... remote position. Application Deadline This position is anticipated to close on Aug 21, 2026. About ...

The Summers Group

Life Insurance Sales Agent

Milwaukee, WI · On-site +1

$30K - $160K/yr

No agent's success, earnings, or production results should be viewed as typical, average, or expected. Not all agents achieve the same or similar results, and no particular results are guaranteed.

Staples, Inc.

Customer Service Representative

Burlington, WI · On-site +1

$17 - $23/hr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... for remote work on Fridays. Staples is business to business. You're what binds us together. At ... Manage inbound and outbound opportunities across multiple lead channels, including web, chat, and ...

Afni, Inc.

Remote Customer Service Representative

Milwaukee, WI · Remote

$15.75 - $21.25/hr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

What You Need to Thrive in Our Remote Environment: * Cable or Fiber Internet Service only (no dial-up, DSL, satellite or cellular) * 25Mbps Download/10Mbps Upload * Ping Rate - Less than 100 ms * A ...

DRUM Associates

Customer Service Representative

Milwaukee, WI · Remote

$24/hr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Remote - but must be location in Wisconsin or Minnesota * Collaborative and team-oriented environment * Opportunity to make a meaningful impact by helping patients receive critical medical equipment ...

All JobsChat Agent JobsRemote Chat Agent JobsRemote Chat Agent Jobs in Milwaukee, WI

Remote Chat Agent information

What are the key skills and qualifications needed to thrive as a remote chat agent, and why are they important?

To thrive as a Remote Chat Agent, you need excellent written communication, strong typing skills, and a high school diploma or equivalent. Familiarity with customer relationship management (CRM) systems, chat platforms, and ticketing software is typically required. Outstanding problem-solving abilities, patience, and attention to detail help agents deliver a positive customer experience. These skills are crucial for efficiently resolving customer inquiries and maintaining high satisfaction in a remote, fast-paced environment.

What does a remote chat agent do?

A remote chat agent answers customer questions through an online chat platform. Your primary responsibilities are to assist customers and troubleshoot issues. You address minor problems and escalate complicated situations to the proper resources. You connect with clients quickly and provide live help. Your duties include using the chat platform, diagnosing the client's problem, communicating until full satisfaction, and assisting with resolutions. A remote chat agent can work in a call center, office environment, or from home.

What is a remote chat agent?

Remote chat agents are customer service professionals who assist customers via online chat platforms, rather than over the phone or in person. They work from a remote location, such as their home, using computers and internet connections to communicate with clients or customers. Their main responsibilities include answering questions, resolving issues, providing product or service information, and ensuring customer satisfaction. Remote chat agents often work for various industries, including retail, technology, and financial services, offering support through live chat, messaging apps, or social media.

What are some common challenges faced by remote chat agents, and how can they be managed effectively?

Remote Chat Agents often encounter challenges such as handling multiple conversations simultaneously, maintaining a consistent and friendly tone, and resolving customer issues efficiently without face-to-face interaction. Effective time management, clear written communication skills, and familiarity with the company’s resources and support tools are essential for success. Many organizations provide training, knowledge bases, and regular team check-ins to help agents stay informed and supported while working remotely.
More about Remote Chat Agent jobs

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For Remote Chat Agent jobs in Milwaukee, WI, the most frequently searched job titles are:

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Remote Chat Agent jobs near you
Infographic showing various Remote Chat Agent job openings in Milwaukee, WI as of August 2026, with employment types broken down into 88% Full Time, 6% Part Time, and 6% Contract. Highlights an 100% Remote job distribution.

Medicare Customer Advisor Licensed Insurance Agent

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Milwaukee, WI • On-site

$39K - $54K/yr

Part-time

Medical, Dental, PTO

Posted yesterday

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Job description

Fully Remote Seasonal Position

Position Overview

We are seeking licensed insurance professionals to join a remote team assisting Medicare customers during the Annual Enrollment Period.

The selected candidates will communicate with customers by telephone and online chat, answer questions about Medicare coverage, and provide enrollment assistance while maintaining a professional customer experience.


Assignment Details

Employment Status: Seasonal Contract

Work Location: Remote

Work Schedule: Full Time

Required Availability: Monday through Saturday

Operating Hours: 8:00 AM to 9:00 PM Eastern Time

Training Commitment: 5 Weeks

Training Structure: 4 Weeks of Classroom Training and 1 Week of Nesting


Core Functions

As part of the team, you will be expected to:

  • Manage incoming customer conversations
  • Respond to questions through phone and chat
  • Discuss Medicare coverage and benefit information
  • Help customers understand available enrollment choices
  • Assist with eligible Medicare plan enrollments
  • Keep customer records and interaction notes accurate
  • Follow required company procedures and compliance guidelines
  • Maintain expected productivity and quality standards

Experience and Licensing

Applicants should meet the following criteria:

  • Hold an active Resident Health Insurance License
  • Maintain license validity through December 8, 2027
  • Have a resident license for the state where you currently live
  • Possess at least one year of customer service experience
  • Demonstrate typing skills of 45 WPM or better
  • Be comfortable using Windows based computer systems
  • Have a High School Diploma or equivalent
  • Be available for the complete Monday through Saturday schedule

Candidates with Medicare, AEP, or insurance sales experience are preferred.


Requirements for Your Workspace


This position requires employees to work from a suitable home office.

Your workspace should be quiet, professional, and appropriate for handling customer conversations.

Internet service must provide at least:

Download Speed: 35 Mbps

Upload Speed: 15 Mbps

A Speedtest.net screenshot may be requested to verify internet performance.

The following internet options are not permitted:

  • Satellite connections
  • Mobile hotspots
  • VPN services
  • Peer to peer networks

Training Process

Before moving into regular customer interactions, new hires will complete five weeks of training.

The program consists of four weeks of classroom instruction followed by one week of nesting, allowing new team members to become familiar with the production environment.

Hiring Locations


Candidates must currently reside in one of these states:

Alabama, Arizona, Arkansas, Delaware, Florida, Georgia, Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana, Maine, Maryland, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, Nevada, New Jersey, New Mexico, North Carolina, North Dakota, Ohio, Oklahoma, Pennsylvania, South Carolina, South Dakota, Tennessee, Texas, Utah, West Virginia, Wisconsin, and Wyoming.

Seasonal Opportunity

This position is offered on a seasonal basis. Depending on business requirements and individual performance, candidates may be considered for future employment opportunities.

If you have an active insurance license, strong customer service abilities, and an interest in Medicare, we invite you to apply.