Product Manager Jobs in Chicago, IL

About us:

Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. Founded in 2017, product launched in 2019, and achieved profitability in 2024.

Why we exist:

Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.

We are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat).

Why we’re hiring:

Our next chapter is about accelerating growth – from 5M to 50M customers by 2030.

This year, we launched 5 new products – home insurance, motorcycle insurance, property tax, car repair, and roadside assistance. But our core product today is our car insurance marketplace, and the opportunity is massive — car insurance alone is a $300B market in the U.S.

We spent the last few years building our supply-side of our marketplace (we work with 100+ insurance carriers), technical infrastructure (60% of policies today are sold automatically without human intervention, 90% of inbound customer inquiries are resolved via AI and automation), and growth engine.

Now, we are focused on redesigning our post-checkout experience to make everything that happens after a customer buys an insurance policy seamless, helpful, and lovable across every moment — including document verification, wallet/payments, policy changes, re-shopping or renewals, and being taken care of when things go wrong.

We're looking for a Senior Product Manager to own this post-purchase customer experience.

Our next goal is to go from 5M to 50M customers and become a $10B business in the next 4 years. Your work will directly accelerate our ability to achieve this.

Who we get excited about:

• Insatiable learner: You are constantly seeking to deepen your knowledge, sharpen your skills, and master whatever craft or goal you’ve set your mind to.

• Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.

• Tenacious: You are highly resilient. No challenge is too difficult, no issue unsolvable.

• Sense of urgency: You have a strong bias for action and are impatient when progress is stalled.

What you bring:

• 5+ years in management consulting (MBB or equivalent), investment banking, venture capital, or consumer-facing product-building experience at a high-growth startup

• Consumer product instincts, either from direct product building experience or from close work alongside product teams

• Comfort with data: able to run your own analysis and build conviction from messy signals

• Ideally, a willingness to work in-person in our Palo Alto office alongside our founders for the first 1-2 months (although not required, we have found that people who spent time with their founders in-person tend to ramp much faster than those who don't)

Compensation:

This position offers base salary and stock options. The base salary for this position within the U.S. is 160,000—210,000 USD, but we can be flexible based on your prior experience and appropriate job levelling. We also offer comprehensive benefits including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with 4% employer matching, and wellness benefits, among others.

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

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 is building the first AI-powered advisor to manage all your physical assets.

Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.

We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.

Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.

We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.