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.ai 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 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. We’ve reached 5M+ customers, raised $240M+, and have been profitable since 2024. We’re now expanding into home, motorcycle, RV, and beyond.

Join a pre-IPO startup with capital ($240M raised), traction (5M+ customers), and runway (we’re profitable). We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto.

About the Role

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.

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. The underlying technology powering our AI is entirely homegrown, handling everything from customer-facing chatbots to vehicle photo validation to back-office automation. However, prompts live across six separate locations with no single source of truth or unified platform. You will own the strategy and execution to consolidate this, as well as drive the future of our AI investments, including voicebot, computer use, and consumer AI applications.

Responsibilities

• Platform Strategy: Define the strategy for migrating prompts from six locations onto a unified platform, sequence the work, align engineering, data, operations, and other teams, and drive execution.
• Chatbot Prioritization: Own the technical prioritization queue, keep the team coordinated, and ensure progress without adding process overhead.
• Emerging Technology Decisions: Track advancements in voicebot and computer use to determine when the technology is ready for serious investment. Own the OpenAI relationship and Jerry’s presence in the ChatGPT store. Bring a point of view and influence AI investment decisions.
• Prompt Engineering: Learn and update prompts, understand interactions across our tech stack (e.g., Propelix, Botly, CRM, GitHub, Replit), and identify bottlenecks.
• Systems Thinking: Dive into technical conversations about API design and system architecture, translating complex concepts for any audience.

Qualifications

• Technologist: You live and breathe AI. You read release notes when new models drop and have built your own custom workflows.
• Systems Thinker: Comfortable discussing API design and system architecture, and translating complex concepts for diverse audiences.
• Experimenter: You think in terms of what’s possible, constantly tinkering with new AI 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 in implementing AI platform standards.

Ideal Experience

• 3+ years 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 turning complex, strategic ideas 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 skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, compensation may include 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 total rewards.

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

Location

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.