Independent Insurance Agent (1099)

About the Opportunity

Partner with one of the fastest-growing fintech startups in the U.S! At Jerry, we’re on a mission to help car owners save time and money on one of their most expensive and high maintenance assets. Since launching our mobile app in 2019, we have amassed over 5M customers, enabling customers to quickly select the best insurance coverage for them.

We are looking for an Independent Insurance Agent to kickstart our local agent channel in the Chicago region as an independent business owner operating under your own license. You’ll grow your business through local partnerships to bring in warm leads, community marketing, and referral relationships — backed by Jerry’s technology, suite of 55+ carrier partners, and support resources.

We’re looking for a hustler — someone who loves meeting people, closing deals, and building something from the ground up. You’ll have the freedom of an entrepreneur with the backing of a fast-growing, venture-funded company.

Why Partner With Jerry

• Unlimited earnings potential with significant commission per policy sold

• Backed by $240M in funding and one of the fastest-growing insurance platforms in the U.S. (60X revenue growth in 5 years)

• Optional technology and back-office tools available at your discretion, so you can focus on growing your own business

• Access to national carriers and real-time quoting through Jerry’s platform

• Opportunity to be part of the founding class of independent agents — shaping how Jerry expands this model nationwide

What You’ll Do

• Build and manage your own book of business as an independent insurance agent representing Jerry

• Develop and maintain local referral partnerships with real estate agents, mortgage brokers, auto dealers, and community organizations

• Use hyperlocal marketing and networking to grow awareness and drive leads in your territory

• Deliver excellent customer experiences while matching clients with the right carriers through Jerry’s platform — using your own sales approach and professional judgement

• Operate as a 1099 independent contractor — you run your business, we provide the tools and support to help it scale

What You’ll Bring

• A current Property & Casualty license in Illinois (required)

• Proven ability to generate and close leads — not afraid to knock on doors, make calls, or show up at local events

• Entrepreneurial drive — motivated by autonomy, growth, and performance-based earnings

• Strong relationship-builder who thrives in-person and in the community

• 2+ years of insurance sales experience preferred (agency, captive, or independent)

• Valid driver’s license and reliable personal vehicle

• Ability to travel locally as determined by your own business strategy across the Chicago area

Please note: Only candidates currently located in the Chicago, Illinois region will be considered for this position.

While we appreciate your interest and application, only applicants under consideration will be contacted.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at [email protected]

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

About Jerry.ai:

Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. 

Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.

We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. 

Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.

Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.