Senior Technical Product Manager, AI Engineering & Systems

Why Jerry.ai?

We are building the first super app to manage car ownership—an industry where the experience is stuck in the 90s.

Lead a strategic area leveraging LLMs, agents, and internal APIs to automate a fragmented, $2T market.

Work with partners at OpenAI to integrate Jerry.ai services directly into the ChatGPT App and pioneer new model capabilities.

Lead the AI Revolution for Jerry.ai:

At Jerry.ai, we are moving past fragmented, time-consuming processes to create a seamless, automated platform.

You will sit at the intersection of product, engineering, and applied AI as you build and scale a sophisticated system that already automates >70% of inbound sales and service requests (over 50k chats per month). Your role will include shaping how modern LLM systems, human-in-the-loop feedback, and computer-use agents redefine an entire industry.

How You Will Make an Impact:

• Lead end-to-end development for our AI platform and customer experiences, from initial roadmap to rollout.

• Partner with engineers to design prompt strategies, evaluation frameworks, and guardrails—balancing latency, cost, and accuracy.

• Serve as the technical translator between engineering and the broader organization, establishing AI best practices and platform standards.

• Drive systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation.

• Work with partners at OpenAI to evaluate and deploy the next generation of voice models and workflow automation.

What We're Looking For in a Builder:

• Intrinsically Motivated Technologist: You live and breathe AI. You read the release notes when a new model drops and you've already built your own custom workflows.

• Systems Thinker: You are comfortable diving into technical conversations about API design and system architecture, translating complex concepts for any audience.

• Optimistic Problem-Solver: You are a "how can we" thinker who seeks constant improvement and thrives on owning high-impact metrics.

• Data-Driven with Conviction: You are familiar with SQL and comfortable diving into the data to answer your own questions and validate hypotheses.

Ideal Profile:

• 4+ years of experience in management consulting or technical product management at a fast-paced startup.

• Proven interest in modern LLM systems.

• Ability to navigate technical tradeoffs and lead by example when implementing AI platform standards.

• A track record of taking complex, strategic ideas and turning them into scalable, production-grade products.

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 View email address on click.appcast.io

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.