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. Work with partners like OpenAI to integrate Jerry.ai 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. You’ll also report directly to our COO, leading one of our most important growth levers.

Why we’re hiring this role:

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. 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. 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.

How you’ll make an impact:

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. Specifically:

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.

Who you are:

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.
Experimenter: You think only in terms of what’s possible. 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.

Ideal experience:

4+ 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 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.

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

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

Your car and your home are your most expensive assets. And for most people, these aren't just purchases, they're the physical embodiment of the life you've 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.

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.

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