1

Progressive Insurance Customer Service Jobs in Wisconsin

Customer Service

Trevor, WI · On-site

$16.75 - $22.25/hr

We are seeking a detail-oriented and analytical Customer Service to join our Sales Support ... Health insurance * Health savings account * Life insurance * Paid time off * Parental leave

Customer Service

Madison, WI · On-site

$14.50 - $20.25/hr

Position SummaryThe Customer Service Associate serves as the frontline and first point of contact ... Benefits401(k)Paid Time Off (PTO)Health insurance benefitsPaid holidaysAnd moreFOR MORE INFORMATION ...

Customer Service

Madison, WI · On-site

$14.50 - $20.25/hr

The Customer Service Associate serves as the frontline and first point of contact for external ... Health insurance benefits * Paid holidays * And more FOR MORE INFORMATION, PLEASE REFER TO UPC ...

Customer Service

Madison, WI · On-site

$14.50 - $20.25/hr

The Customer Service Associate serves as the frontline and first point of contact for external ... Health insurance benefits * Paid holidays * And more FOR MORE INFORMATION, PLEASE REFER TO UPC ...

Customer Service

Monona, WI · On-site

$15 - $20.75/hr

The Customer Service Associate serves as the frontline and first point of contact for external ... Health insurance benefits * Paid holidays * And more FOR MORE INFORMATION, PLEASE REFER TO UPC ...

Customer Service

Madison, WI · On-site

$16 - $22/hr

Customer Service Department: General FLSA: Hourly Revision Date: 07/2026 About Hy-Vee At Hy-Vee, we ... insured mail * Process Western Union orders and send faxes for customers * Sell money orders and ...

Customer Service

Madison, WI · On-site

$16 - $22/hr

Customer Service Department: General FLSA: Hourly Revision Date: 07/2026 About Hy-Vee At Hy-Vee, we ... insured mail * Process Western Union orders and send faxes for customers * Sell money orders and ...

Customer Service

Madison, WI · On-site

$16 - $22/hr

Customer Service Department: General FLSA: Hourly Revision Date: 07/2026 About Hy-Vee At Hy-Vee, we ... insured mail * Process Western Union orders and send faxes for customers * Sell money orders and ...

Customer Service

Madison, WI · On-site

$16 - $22/hr

Customer Service Department: General FLSA: Hourly Revision Date: 07/2026 About Hy-Vee At Hy-Vee, we ... insured mail * Process Western Union orders and send faxes for customers * Sell money orders and ...

Customer Service

Madison, WI · On-site

$16 - $22/hr

Customer Service Department: General FLSA: Hourly Revision Date: 07/2026 About Hy-Vee At Hy-Vee, we ... insured mail * Process Western Union orders and send faxes for customers * Sell money orders and ...

Customer Service

Madison, WI · On-site

$16 - $22/hr

Customer Service Department: Grocery FLSA : Non-Exempt General Function Responsible for processing ... insured mail. * Processes Western Union orders. * Processes Western Union orders. * Sells money ...

Showing results 41-60

Progressive Insurance Customer Service information

What is the difference between Progressive Insurance Customer Service vs Claims Adjuster?

AspectProgressive Insurance Customer ServiceClaims Adjuster
Required CredentialsHigh school diploma or equivalent; some roles may prefer customer service certificationsHigh school diploma or equivalent; relevant licensing or certifications often required
Work EnvironmentCall centers, online support, in-person branchesField and office settings, inspecting damages, negotiating claims
Employer & Industry UsageInsurance companies, customer support centersInsurance companies, claims departments
Common Search & ComparisonCustomer service roles in insuranceClaims handling and adjustment roles

Progressive Insurance Customer Service representatives primarily handle policy inquiries, billing, and general support via calls or online platforms. Claims Adjusters focus on investigating and settling insurance claims, often requiring fieldwork and specialized training. While both roles work within the insurance industry, they differ in responsibilities, work environment, and required skills.

What are the key skills and qualifications needed to thrive as a Progressive Insurance Customer Service representative?

To excel as a Progressive Insurance Customer Service Representative, you need strong communication, problem-solving, and organizational skills, typically supported by a high school diploma or equivalent. Familiarity with customer relationship management (CRM) software, call center telephony systems, and basic insurance concepts or licenses is often required. Patience, active listening, and a customer-focused attitude help you stand out in handling diverse customer needs and resolving issues. These skills ensure efficient service, customer satisfaction, and adherence to company standards in a fast-paced insurance environment.

What are some common challenges faced by Progressive Insurance Customer Service representatives and how are they addressed?

Progressive Insurance Customer Service representatives often handle a high volume of diverse customer inquiries, ranging from policy questions to claims assistance. Balancing efficiency with empathy can be challenging, especially during peak periods or when dealing with upset customers. To address these challenges, Progressive provides comprehensive training, ongoing support from supervisors, and user-friendly technology to streamline tasks. Team collaboration and regular feedback sessions also help representatives continuously improve their problem-solving and communication skills.

What does a Progressive Insurance Customer Service representative do?

A Progressive Insurance Customer Service representative assists customers with questions about their insurance policies, helps file and manage claims, processes payments, updates account information, and resolves billing or coverage issues. They serve as the main point of contact for customers, providing support via phone, email, or online chat. Representatives aim to deliver prompt, friendly, and knowledgeable service to ensure customer satisfaction and retention.

Is Progressive Insurance Customer Service a good job?

Progressive Insurance Customer Service roles typically involve assisting customers with policy inquiries, claims, and billing, often requiring strong communication skills and familiarity with insurance products. The job can offer competitive pay, benefits, and opportunities for advancement, but may also involve high call volumes and performance metrics. Overall, it is considered a stable entry-level position within the insurance industry.

What are popular job titles related to Progressive Insurance Customer Service jobs in Wisconsin?

For Progressive Insurance Customer Service jobs in Wisconsin, the most frequently searched job titles are:

Infographic showing various Progressive Insurance Customer Service job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 79% Full Time, 17% Part Time, and 3% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution.

Insurance Sales Agent - Customer Service

Freeway Insurance

Milwaukee, WI • On-site

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 12 days ago


Freeway Insurance rating

8.2

Company rating: 8.2 out of 10

Based on 12 frontline employees who took The Breakroom Quiz

141st of 308 rated insurance


Job description

Sign-On Bonus Opportunity of up to $1,000*

Our Perks:

  • Unlimited/Uncapped commission
  • Lucrative incentive sales plans, bonuses and sales contests
  • No Cold Calling- We have a high volume of inbound sales leads and walk in traffic
  • Comprehensive paid training and licensing with continuous on-going training and mentorship
  • Recognition culture
  • Comprehensive Benefits package including medical, dental, vision and life insurance
  • Retirement Plan: A 401K plan with a percentage of company-matched contributions
  • Fitness: We reimburse up to $15 a month to an employee for their gym
  • Employee Assistance Program: Confidential assistance to you or anyone in your household who is experiencing personal or professional problems — at no cost
  • Extra Perks: Access to disability, hospital indemnity, health advocate program, universal life, critical illness, and accident insurance plans. We even offer pet insurance

Our Company:

Confie and its family of companies - Freeway, Baja, Bluefire & others - is one of the largest privately held insurance brokers in the United States and has been ranked the #1 Personal Lines Leader by the Insurance Journal for the seventh straight year!. With over 800 retail store locations to choose from nationwide, we encourage you to take your career and income potential to new heights! We are proactively looking for brighttalented, and motivated individuals who are goal oriented and excited for career advancement. Come Grow With Us!

What You Will Do:

As an Insurance Agent you will be responsible primarily for the sale of nonstandard auto insurance to new and existing customers.

  • Solicit new business and maintain current business levels in order to achieve or exceed sales production goals.
  • Expand business by proactively building relationships with existing customers to meet the agreed upon production goals.
  • Accurate accounting of all currency transactions as well as timely delivery of deposits to the bank with scanned documentation in agency management system.
  • Connects very quickly; builds and leverages client relationships. Ability to educate and advise the customer on which products best fit their needs

The Perfect Match:

  • Personal Lines or Property and Casualty license preferred (but not required)
  • Bilingual in English and Spanish preferred
  • Sales or customer service experience
  • High School Diploma or GED
  • Ability to build relationships with sales customers
  • Excellent follow-up and multi-tasking skills
  • Ambitious professional motivated by opportunity for advancement
  • Excellent written and verbal communication skills

Insurance Sales
Insurance Agent
Hiring Immediately
Freeway Auto Insurance

As permitted by applicable law and from time-to-time, Confie may use a computer system that has elements of artificial intelligence to help make decisions about your employment, including recruitment, hiring, renewal of employment, or the terms and conditions of your employment. Employees with questions about Confie’s use of these computer systems should contact Human Resources at employeerelations@confie.com


What Freeway Insurance employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom