ai ? We are building the first super app to manage car ownership—an industry where the experience is stuck in the 90s. ai services directly into the ChatGPT App and pioneer new model capabilities. Lead The AI Revolution For Jerry.ai 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 - building and scaling 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. Lead end-to-end development for our AI platform and customer experiences, from initial roadmap to rollout. 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.

Intrinsically Motivated Technologist: You live and breathe AI.

Systems Thinker: You are comfortable diving into technical conversations about API design and system architecture, translating complex concepts for any audience. Data-Driven with Conviction: You are familiar with SQL and comfortable diving into the data to answer your own questions and validate hypotheses. 4+ years of experience in management consulting or technical product management at a fast-paced startup. ~ Ability to navigate technical tradeoffs and lead by example when implementing AI platform standards. ~ 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.

- 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 ai 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.

ai 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 have more than 5 million customers — and we’re just getting started. ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.

Help us build a revolutionary product that’s disrupting a massive market. #

📌 Head of Product & Regulatory, Legal (Toronto)
🏢 Socket.dev
📍 Toronto