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Progressive Insurance Agent Jobs in Chicago, IL (NOW HIRING)

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Progressive Insurance Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.3K

How much do progressive insurance agent jobs pay per year?

As of Aug 8, 2026, the average yearly pay for progressive insurance agent in Chicago, IL is $67,035.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,900.00 and $79,400.00 per year, depending on experience, location, and employer.

What is the difference between Progressive Insurance Agent vs State Farm Insurance Agent?

AspectProgressive Insurance AgentState Farm Insurance Agent
Required CredentialsLicensing in insurance sales, state-specific licensesLicensing in insurance sales, state-specific licenses
Work EnvironmentOffice-based, independent agency settingsOffice-based, agency offices
Employer & Industry UsagePart of Progressive Corporation, auto and property insurancePart of State Farm, auto, home, and life insurance
Common Search & ComparisonOften compared for auto insurance sales rolesSimilar roles in auto and property insurance sales

Both Progressive Insurance Agents and State Farm Insurance Agents require similar licensing and work in office environments selling auto and property insurance. The main difference lies in their parent companies and product focus, with Progressive emphasizing auto and property insurance, while State Farm offers a broader range including life insurance. They serve similar customer needs and are often compared by job seekers exploring insurance sales roles.

What is a Progressive Insurance Agent?

Progressive Insurance Agents are licensed professionals who sell and service insurance products offered by Progressive, one of the largest auto insurers in the United States. They help customers compare coverage options, provide personalized policy recommendations, and assist with claims or policy changes. Some agents work exclusively with Progressive, while others are independent and can offer products from multiple insurance companies. Their goal is to help customers find the right coverage to meet their needs and budget, often providing ongoing support throughout the policy term.

What are some typical challenges Progressive Insurance Agents face, and how can they prepare for them?

Progressive Insurance Agents often encounter challenges such as navigating a highly competitive market, meeting sales targets, and staying updated on constantly evolving insurance products and regulations. To succeed, agents should focus on building strong client relationships, actively participate in ongoing training offered by Progressive, and utilize digital tools for efficient client management. Being proactive in learning about new products and maintaining excellent communication skills are key strategies for overcoming these challenges and achieving long-term success in the role.
Progressive Insurance Agent jobs near you
Infographic showing various Progressive Insurance Agent job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution, with an average salary of $67,035 per year, or $32.2 per hour.

Insurance Agent Hiring Event | In-Person Interviews | St. Charles, IL

Comparion Insurance Agency

Saint Charles, IL • On-site

Full-time

Medical, Retirement, PTO

Posted 5 days ago

Job description


Description
Insurance Agent Hiring Event | In-Person Interviews | Illinois

We are hosting exclusive, invitation-only, in-person interviews on August 19, 2026 for motivated professionals interested in a rewarding career in insurance sales.

If you are interested in attending, reserve your spot by clicking APPLY NOW. Due to limited availability, only selected candidates will receive an invitation to attend.

At this event, you will have the opportunity to:

  • Participate in a one-on-one interview with our Agency Manager
  • Job shadow and learn about a day in the life of a successful Insurance Agent
  • Explore career growth opportunities and earning potential
  • Learn more about our award-winning sales culture and training program

Comparion Insurance Agency is hiring self-motivated, relationship-driven professionals for a rewarding outside sales career. This role does require meeting in-office requirements and working closely with your local agency team.

This position offers the autonomy and flexibility to build your career, grow your earnings, and make a meaningful impact by helping protect individuals and families with auto, home, life, and specialty insurance products.

Backed by a Fortune 100 company, you'll receive hands-on training, industry-leading resources, and ongoing team support to help you succeed. No prior insurance experience is required. We are looking for individuals with strong communication skills, a passion for helping others, and a drive to achieve sales success.

Space is limited. Apply today to be considered for this exclusive hiring event.

Description

What you’ll do:

  • Sell auto, home, life, and related insurance products using a consultative, needs-based approach.
  • Build and maintain a book of business through referrals, networking, and community engagement as part of your outside sales efforts.
  • Identify prospective customers using established lead methodologies and relationship-driven outreach.
  • Accurately document customer interactions and handle sensitive information with integrity and confidentiality.
  • Use insurance sales technology, relationship management tools, and multi-carrier platforms to deliver tailored insurance solutions.
  • Participate in training, coaching, and performance incentives to continuously improve sales results.

What We Offer:

  • Unlimited commission and renewal income – potential for earnings growth over time.
  • Full-time employment with benefits from day one, including health insurance, generous 401(k) match, and paid time off.
  • Paid training, licensing support, and ongoing development.
  • Autonomy to embrace your entrepreneurial spirit and structure your time your way.
  • Flexible work structure (hybrid office, field, and remote based on what your day requires).
  • Supportive team culture with mentorship and long-term career paths.
Qualifications

Who We’re Looking For:

Day One Skills & Traits

  • Self-motivated and accountable – you take ownership of your work and results.
  • Reliable and responsive – you follow through and do what you say you’ll do.
  • Professional and trustworthy – you handle customer information with care and integrity.
  • Relationship-focused – you enjoy helping others and building long-term trust.
  • Outgoing – you’re comfortable talking with people and explaining options clearly.
  • Tech savvy – you’re able to learn and use technology and digital tools with ease.
  • Calm under pressure – you stay composed in a fast-paced, customer-focused environment.

Preferred Qualifications

  • Experience in customer-facing roles like retail, hospitality, service, operations, logistics, banking, account management, or sales.
  • Basic understanding of sales conversations, including handling common customer questions or objections.
  • Experience managing multiple accounts, clients, or priorities simultaneously.
  • Exposure to consultative selling, negotiation, or regulated industries.

You will be required to obtain relevant licenses upon being hired.

 

Build a career for yourself, not by yourself. Launch a rewarding insurance sales career today.

About Us

Pay Philosophy: The typical starting salary range for this role is determined by a number of factors including skills, experience, education, certifications and location. The full salary range for this role reflects the competitive labor market value for all employees in these positions across the national market and provides an opportunity to progress as employees grow and develop within the role. Some roles at Liberty Mutual have a corresponding compensation plan which may include commission and/or bonus earnings at rates that vary based on multiple factors set forth in the compensation plan for the role.

In 2022, Comparion Insurance Agency was created to transition former Liberty Mutual exclusive agents to an agency that delivers a unique value proposition to carriers with over 2,000 agents in approximately 180 cities in 44 states. We offer customers 50 insurance companies with product breadth including auto, home, life, pet, renters, umbrella, jewelry and much more. We use our scale to deliver a first-rate customer experience through consultative insurance experts located in their communities.

Our Leadership team has over 200 years of cumulative insurance experience. At Comparion, we have a philosophy of staying close to our customers and agents, so sales leadership is located throughout the country in our larger storefronts. Comparion is owned and backed by Liberty Mutual Group, a Fortune 100 company, founded in 1912

Liberty Mutual is an equal opportunity employer. We will not tolerate discrimination on the basis of race, color, national origin, sex, sexual orientation, gender identity, religion, age, disability, veteran's status, pregnancy, genetic information or on any basis prohibited by federal, state or local law. 
 
Fair Chance Notices

  • California
  • Los Angeles Incorporated
  • Los Angeles Unincorporated
  • Philadelphia
  • San Francisco

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