Senior product manager

Jerry
Chicago, IL

About Jerry.ai

Jerry.ai is building America’s first and only AI-powered 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. 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 users, and have helped millions find better auto insurance — and we’re just getting started.

About The Opportunity

We are looking for a Senior Product Manager to own Jerry.ai’s AI driven communications product. AI and automation are a key component of Jerry.ai’s growth strategy, driving the engagement, conversion, and retention of our customer base. Today, over 70% of customer requests are handled using AI agents built using our internal AI agent development platform, Propelix. Our goal is to increase this number to over 90%, while increasing customer satisfaction and conversion with AI interactions that delight our customers. The messaging infrastructure underlying these communications across SMS, in-app chat, email, and voice, is critical to the success of the platform, and we need your help to scale it up.

How You’ll Make An Impact:

  • Partner closely with our Product, Engineering, and Data Science teams to create lovable AI interactions that increase automation and customer satisfaction.
  • Analyze data to identify and prioritize improvements to our core messaging systems.
  • Identify bottlenecks to solving high-impact issues to shape both our prompt engineering best practices and our technical roadmap.
  • Stay on top of AI trends, best practices, and tech to make strategic decisions.


Who You Are

  • You have 5+ years of experience in management consulting, technical product management, data analytics, or operations at a fast paced startup.
  • You’re a technologist and a systems thinker. You’re comfortable in technical conversations and can translate complex ideas into simple terms.
  • You’re data-driven, familiar with SQL, and comfortable diving into data to answer your own questions.
  • You like to own metrics, and constantly seek improvement. You’re an optimist who asks “how we can” not “if we can.”
  • You’re passionate about AI. You use it to automate your day to day, you’re an early adopter of the latest and greatest, and you want to be at the vanguard of leveraging it at scale to deliver outstanding, personalized customer communications.


Why You’ll Love It

  • Join a pre-IPO startup with capital, traction, and runway ($240M funded | 60X revenue growth in 5 years | $2T market size)
  • Work closely with brilliant leaders and teammates from companies like Amazon, Better, LinkedIn, Nerdwallet, McKinsey, BCG, Bain, Andreessen Horowitz
  • 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
  • Impact millions of users experience with car maintenance and auto insurance


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.
Posted 2025-10-06

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