Senior Technical Product Manager, AI Engineering & Systems

About Jerry.ai

Your car and your home are your most expensive assets. 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. Jerry is building the first AI agent to manage all your physical assets.

We launched car insurance in 2019 and became one of the top three brokers in the U.S. 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.

About the Role

Join a pre-IPO startup with capital ($240M raised), traction (5M+ customers), and runway (we’re profitable). Impact: 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.

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. The underlying AI technology is entirely homegrown, handling a meaningful share of customer interactions end-to-end. However, the system has grown complex, with prompts powering everything from the customer-facing chatbot to vehicle photo validation to back-office automation spread 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.

Responsibilities

• Keep the current AI platform running while driving the architectural decisions that determine its future state.
• In the first few months: Learn the prompt engineering workflow by writing and updating prompts, understanding how our tech stacks (e.g., Propelix, Botly, CRM, GitHub, and Replit) interact, and identifying bottlenecks.
• 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, keeping the team coordinated and moving without adding process overhead.
• Emerging technology decisions: Track voicebot and computer use closely to know when the technology crosses the threshold for serious investment. Own the OpenAI relationship and the Jerry presence in the ChatGPT store. Bring a point of view and influence our AI investment decisions.

Qualifications

• Technologist: You live and breathe AI. You read the release notes when a new model drops and have built your own custom workflows.
• Systems Thinker: 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.
• Data-Driven: Familiar with SQL and comfortable diving into data to answer questions and validate hypotheses.
• Pragmatic: 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.
• Track record of taking complex, strategic ideas and turning them into scalable, production-grade products.

Pay

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.

Benefits

• Comprehensive health, dental, and vision coverage.
• Paid time off and paid parental leave.
• 401(K) plan with employer matching.
• Wellness benefits.
• Equity opportunities as part of your total rewards package.

Part-time, contract, or freelance roles may not be eligible for certain benefits.

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.