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

Comparion Insurance Agency is hiring self-motivated, relationship-driven professionals for a rewarding outside sales career.  This role has IN OFFICE requirements.  Must reside in the state of Illinois. This role offers 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.

Backed by a Fortune 100 company, you'll receive hands-on training, resources, and team support to help you succeed - no prior insurance experience required.

Pay Details

• The typical training salary is $55k - $65k
• Through a combination of base, bonuses, and uncapped commissions, typical total first year compensation ranges from $55k - $75k
• Potential for top performers to earn over $100k in their first year

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.

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.

Employees should review all role requirements and apply only for positions for which they are eligible. Hiring processes may vary by country, including differences in procedures, requirements, and timelines.  For country-specific details, please consult your local recruiting / HR team.

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.At Liberty Mutual, our goal is to create a workplace where everyone feels valued, supported, and can thrive. We build an environment that welcomes a wide range of perspectives and experiences, with inclusion embedded in every aspect of our culture and reflected in everyday interactions. This comes to life through comprehensive benefits, workplace flexibility, professional development opportunities, and a host of opportunities provided through our Employee Resource Groups. Each employee plays a role in creating our inclusive culture, which supports every individual to do their best work. Together, we cultivate a community where everyone can make a meaningful impact for our business, our customers, and the communities we serve. We value your hard work, integrity and commitment to make things better, and we put people first by offering you benefits that support your life and well-being. To learn more about our benefit offerings please visit: https://www.libertymutualgroup.com/about-lm/careers/benefitsLiberty 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