Technical Product Manager, AI Engineering & Systems

• Join a pre-IPO startup with capital ($240M raised) traction (5M customers) and runway (were profitable).

• Impact: Come lead our customer-facing Agentic AI product leveraging LLMs agents and internal APIs to create a magical experience for our customers. Work with partners like OpenAI to integrate services directly into the ChatGPT App and pioneer new model capabilities.

• Accelerated career growth. We have a flat org chart ambitious goals and no shortage of opportunities for people who want more. Youll also report directly to our COO leading one of our most important growth levers.

Your car and your home are your most important assets yet the experience of owning one is stuck in the 90s. Every part of the journey buy/sell insurance maintenance repairs is fragmented complicated and expensive. is building the first app to manage it all.

We launched car insurance in 2019 and became one of the top three brokers in the country. We got there in part because we were early on generative AI. Before off-the-shelf platforms existed we built our own infrastructure to automate sales and service conversations. Today that system handles a meaningful share of customer interactions end-to-end. The underlying technology is entirely homegrown.

That head start created real leverage. It also created real complexity. Prompts that power everything from the customer-facing chatbot to vehicle photo validation to back-office automation now live across six separate locations. There is no single source of truth no unified platform and no clear owner of where the next big bets voicebot computer use consumer AI applications belong on the roadmap. That is what you will own.

Your scope will cover two layers: keeping the current AI platform running while driving the architectural decisions that determine its future state.

In the first few months you will learn the prompt engineering workflow through writing and updating prompts understanding how our various tech stacks (e.g. Propelix Botly CRM GitHub and Replit) interact and getting a ground-level view of where the bottlenecks are. After that you will start owning the platform strategy:

• Prompt consolidation. Define the strategy for migrating prompts from six locations onto a unified platform sequencing the work aligning engineering data operations and other teams on the plan and driving execution.

• Chatbot prioritization. Own the technical prioritization queue. Keep the team coordinated and moving without adding process overhead.

• Emerging technology decisions. Track voicebot and computer use closely enough to know when the technology crosses the threshold for serious investment. Own the OpenAI relationship and the Jerry presence in the ChatGPT store. These are not passive monitoring tasks you will be expected to bring a point of view and influence our AI investment decisions.

• Technologist: You live and breathe AI. You read the release notes when a new model drops and youve 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.

• Experimenter: You think only in terms of whats possible. AI is rapidly evolving and youre constantly tinkering and finding new capabilities that didnt exist yesterday.

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

• Pragmatic: You can navigate technical tradeoffs and lead by example when implementing AI platform standards.

• 3 years of experience in a technical role like forward deployed engineering technical product management or similar at a fast-paced startup.

• Passion and curiosity for AI systems including modern LLMs etc.

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

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

Please note: is only able to hire employees who currently reside in AZ CA CO FL GA IL MA NC NJ NV NY OR TN TX UT VA or Ontario Canada. We cannot accept applications from candidates residing elsewhere at this time.

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.

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

The successful candidates 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 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

Your car and your home are your most expensive assets. And for most people these arent just purchases theyre the physical embodiment of the life youve 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 or worse an accident and help you sell at the best price when the time is right. That friend is Jerry.

Jerry is building the first AI agent to manage all your physical assets. 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.

Weve reached 5M customers raised $240M and have been profitable since 2024. Were now expanding into home motorcycle RV and beyond.

Were fully remote with offices in Palo Alto New York Chicago and Toronto.

Required Experience:

IC