Online Chat Operator Jobs in Delafield, WI (NOW HIRING)

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.