Area Manager (Chicago)

You could be building a market anywhere. Why us?

• Join a pre-IPO startup with capital, traction, and runway ($240M funded | 60X revenue growth in 5 years | $2T market size)

• Report directly to Director of New Partnerships who scaled Bird across North and Latin America.

• Pioneer a brand-new, critical business line—the Independent Agent Network—that is essential for our next phase of growth

• Disrupt a massive market and take us to a $10B business in the next few years

• Be immersed in a talent-dense environment and greatly accelerate your career growth

About the opportunity:

Jerry is growing and looking for an entrepreneurial and results-driven Area Manager to launch and manage our Independent Agent Network in the Chicago market! You will be the first person on the ground, responsible for building our foundational book of business from 0-1. As a key early member of the New Partnerships team, you will champion data-driven strategies to create a strong local brand presence and build a pipeline of high-value local referral partners across the entire car ownership ecosystem (insurance, real estate, auto, repair, etc.).

Jerry is building the first super app to make car ownership affordable and accessible – insurance, buy/sell, registration, loans, safety, repairs, parking, etc – a $2T market in the U.S. We have amassed over 5M customers, raised $240M in funding, and scaled our revenue 60X.

How you will make an impact:

• Forge Critical Local Partnerships: Drive referral growth by identifying, pitching, and closing high-value partnerships across the Chicago metro area, including dealerships, repair shops, real estate agencies, and other relevant entities.

• Pioneer the Operational Playbook: Build the foundational book of business and establish the repeatable processes, tools, and strategies that will serve as the national blueprint for future Independent Agent Network expansion.

• Scale the Success: Recruit, train, and lead a high-performing team of agents, providing mentorship and setting aggressive growth targets to ensure sustainable market penetration and APUM growth.

• Serve as Jerry's Key Ambassador: Act as the face of Jerry in the Chicago market, representing the company at industry, community, and partner events to build brand awareness and establish trust.

What you bring:

• 3+ years of experience in insurance sales, business development, or regional/territory management

• Proven track record of building complex relationships and successfully closing partnerships in the local market

• Demonstrated leadership experience in hiring, training, or managing agents or high-velocity sales teams

• Strong verbal and written communication skills suitable for external partnership development and internal reporting

• Valid driver’s license and reliable personal vehicle

• Willingness to travel locally 50–70% of the time across the Chicago metro area to meet partners and agents

Who you are:

• Entrepreneurial mindset: You are comfortable with ambiguity, motivated by ownership, and driven entirely by growth in an environment where success is defined by your hustle and execution.

• High Bar for Excellence: You set a very high bar for yourself and for your team, and you are constantly pushing that bar higher in the pursuit of excellence.

• True Builder: You are energized by the challenge of developing a new business line from nothing and have a framework for problem-solving that is rooted in first principles.

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 recruiting@jerry.ai

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.