AI Systems Architect

Our AI agents and automation system, which has two components: Agentic/conversational front end — chatbot, voicebot, computer-use agents; shape what the prompt engineering team builds next and keep the architecture sound as it scales. Backend workflow automation — build new automations for things like document validation (ex. licenses, proof of insurance), record disputes, transaction orchestration with external carrier systems.

Agentic/conversational front end — chatbot, voicebot, computer-use agents; shape what the prompt engineering team builds next and keep the architecture sound as it scales.

Backend workflow automation — build new automations for things like document validation (ex. licenses, proof of insurance), record disputes, transaction orchestration with external carrier systems.

Evaluate emerging AI technology (voicebot, computer use agents, and beyond), make the call on what we invest in next, build and ship to production.

Partner with OpenAI to evaluate and deploy next-generation voice models and workflow automation.

5+ years in software engineering, ideally at an early-stage startup where you’ve owned outcomes end-to-end.

You are a builder at heart. You don't need someone else to write the spec.

You've tinkered with a new model within days of its release, and you can explain why one architecture or approach is superior to another.

Experience putting LLM-based systems into production, including the unglamorous parts: evals, regressions, latency, cost, and failure-handling.

Our tech stack: TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda), LLM models (OpenAI, Anthropic Claude, Google Gemini)

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.

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 recruiting@jerry.ai

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.

Jerry is building the first AI-powered advisor to manage all your physical assets.

Your car, home, and motorcycle 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, and help you sell at the best price when the time is right. That friend is Jerry.

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.

Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.

We are a remote-first company, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.