Why Jerry.ai? - Join a pre-IPO startup with capital ($240M raised), traction (5M customers), and runway (we’re profitable). - Impact: Come lead our customer-facing Agentic AI product leveraging LLMs, agents, and internal APIs to create a magical experience for our customers. ai services directly into the ChatGPT App and pioneer new model capabilities. - You’ll 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. Jerry.ai 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. 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. 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: - 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. - Track voicebot and computer use closely enough to know when the technology crosses the threshold for serious investment. 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. AI is rapidly evolving, and you’re constantly tinkering and finding new capabilities that didn’t 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: 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. 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 recruiting@jerry.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 Your car and your home are your most expensive assets. 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. 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.We've reached 5M customers, raised $240M, and have been profitable since 2024. We're now expanding into home, motorcycle, RV, and beyond. We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto.5c143e31-5e48-4549-b638-05792d185386