Why you should join us:
Jerry.ai is a profitable, Series C, YC-backed tech startup with 5M+ customers and $240M in funding. We’re building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.
The opportunity is massive — car insurance alone is a $300B market in the U.S. We spent the last few years building our supply (we work with 100+ insurance carriers) and our technical infrastructure (60% of policies today are sold automatically without human intervention, 90% of inbound customer inquiries are resolved via AI and automation). The next chapter is about accelerating our growth — going from 5M to 50M customers by 2030.
The technical challenge:
Our insurance marketplace is our core product today, and our ability to automate the end-to-end shopping experience is our core differentiator. The AI & Automation team owns the most critical part of that – how we automate the entire insurance quoting experience for our customers and orchestrate complex, multi-step transactions with external insurance provider systems to finalize policy purchases.
Before off-the-shelf AI agents existed, we built our own proprietary infrastructure to scale automated insurance purchases and customer support. Today, 60% of insurance policies are sold automatically without human intervention, and 78% of inbound customer inquiries are resolved via AI and automation, with 83% reporting a positive experience.
Our current system is working but our use cases are rapidly growing as our business expands beyond car insurance and available AI models are also evolving. We need someone to lead the charge in building our “next generation” AI system, including building new automations for things like document validation (drivers’ licenses, proof of insurance, etc), voicebot expansion into stateful, phone-based interactions, and enable our bots to have direct external system navigation to resolve complex issues more quickly and accurately than human agents.
Note: You may see different job ads for this role at different job levels. We are only hiring one person. Our priority is finding the right person, we can be flexible with job title/leveling.
What you’ll own:
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.
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.
Who you are:
5+ years owning product strategy and execution for a technical product, ideally at an early-stage startup, where you worked hands-on enough with engineering to make technical tradeoff calls.
You've made a call between two valid technical approaches based on business impact, not just technical elegance, and can reason through why.
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 [email protected]
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
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.
Jerry Toronto, Ontario, CAN Office
Toronto, Canada
