
Job Overview
Location
Chicago
Job Type
Full-time
Category
Sales
Date Posted
February 23, 2026
Full Job Description
đź“‹ Description
- • Join Jerry.ai, a trailblazing fintech startup poised to revolutionize car ownership, and become a foundational member of our independent agent network. As a rapidly growing company with over 5 million customers and significant venture funding, Jerry is expanding its reach by empowering entrepreneurial individuals to build and manage their own insurance businesses.
- • This is a unique opportunity to operate as an independent business owner under your own license, focusing on the vibrant Chicago region. You will leverage Jerry's cutting-edge technology, extensive network of 55+ carrier partners, and robust support resources to establish and grow your client base.
- • Your primary mission will be to cultivate and manage your own book of business as an independent insurance agent, acting as a trusted advisor for car owners seeking optimal insurance solutions.
- • You will be instrumental in developing and nurturing strategic local referral partnerships. This includes forging strong relationships with real estate agents, mortgage brokers, auto dealerships, and diverse community organizations to create a consistent flow of warm leads.
- • A key aspect of your role will involve implementing hyperlocal marketing and networking strategies. This proactive approach will drive brand awareness and generate leads within your designated territory, establishing Jerry as the go-to insurance solution in the Chicago community.
- • You will be responsible for delivering an exceptional customer experience at every touchpoint. This involves expertly matching clients with the most suitable carriers and coverage options, utilizing Jerry's advanced platform while applying your own personalized sales approach and professional judgment.
- • As a 1099 independent contractor, you will have the autonomy to run your business your way. Jerry provides the essential tools, technology, and support infrastructure, enabling you to focus your energy on scaling your operations and maximizing your earning potential.
- • This role is ideal for a self-starter with an entrepreneurial spirit, someone who thrives on building relationships, closing deals, and achieving ambitious goals. You will have the freedom to innovate and the backing of a financially strong and rapidly expanding company.
- • You will gain access to Jerry's proprietary platform, which offers real-time quoting capabilities across a wide array of national carriers, streamlining the sales process and enhancing your ability to serve clients efficiently.
- • Become part of the inaugural class of independent agents, playing a pivotal role in shaping and refining Jerry's expansion strategy for this innovative business model nationwide.
- • Your success will be directly tied to your ability to generate leads, build trust, and provide outstanding service, all while operating with the independence of a business owner.
- • This is more than just selling insurance; it's about building a sustainable business, fostering community connections, and contributing to the growth of a disruptive force in the automotive and fintech industries.
- • You will be empowered to define your own success metrics and business development strategies, with the full support of Jerry's dedicated resources.
- • Embrace the challenge of building something from the ground up, driven by a passion for entrepreneurship and a commitment to client satisfaction.
- • Your role is crucial in bringing Jerry's mission of simplifying car ownership and saving customers time and money to life within the local Chicago market.
- • You will have the opportunity to earn unlimited income, with significant commission potential for every policy you successfully place.
- • Benefit from the stability and growth trajectory of a company that has secured over $240 million in funding and achieved remarkable revenue growth.
- • Utilize optional technology and back-office tools at your discretion, allowing you to tailor your operational setup for maximum efficiency and business growth.
- • This position offers a dynamic blend of entrepreneurial freedom and corporate support, making it an unparalleled opportunity for ambitious sales professionals.
🎯 Requirements
- • Current Property & Casualty license in Illinois.
- • Proven ability to generate and close leads, with a proactive and tenacious sales approach.
- • Demonstrated entrepreneurial drive and a strong motivation for performance-based earnings and autonomy.
- • Excellent relationship-building skills and a comfort level with in-person networking and community engagement.
- • At least 2 years of insurance sales experience (agency, captive, or independent) is preferred.
- • Valid driver's license and reliable personal vehicle for local travel.
🏖️ Benefits
- • Unlimited earning potential with significant commission per policy sold.
- • Backed by $240M in funding and one of the fastest-growing insurance platforms in the U.S.
- • Access to national carriers and real-time quoting through Jerry's platform.
- • Opportunity to be part of the founding class of independent agents, shaping a nationwide expansion model.
Skills & Technologies
About Jerry Technologies, Inc.
Jerry is a technology company focused on simplifying and personalizing the car ownership experience. They offer a mobile app that acts as a digital assistant for car owners, providing services such as insurance comparison and purchasing, maintenance scheduling, roadside assistance, and parking assistance. Jerry aims to reduce the stress and cost associated with owning a vehicle by leveraging AI and data analytics to offer tailored solutions and competitive pricing. Their platform connects users with a network of service providers and insurance carriers, streamlining the entire car ownership lifecycle.
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