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Jerry.ai is a profitable, Series C, YC-backed fintech startup with 5M+ customers and $240M in funding. The company is building an AI-powered advisor to manage physical assets, starting with car insurance (a $300B market) and expanding into home, motorcycle, RV, and boat insurance. The company has achieved significant automation milestones: 60% of policies are sold automatically without human intervention, and 78% of inbound customer inquiries are resolved via AI with 83% positive experience ratings.
You will own the AI agents and automation system, which comprises two critical components: (1) the agentic/conversational front end (chatbot, voicebot, computer-use agents) where you'll shape the prompt engineering team's roadmap and maintain architectural soundness as it scales, and (2) backend workflow automation for document validation (driver's licenses, proof of insurance), record disputes, and transaction orchestration with external carrier systems.
Key responsibilities include evaluating emerging AI technologies (voicebot, computer-use agents, and beyond) and making investment decisions, building and shipping new automations to production, and partnering with OpenAI to evaluate and deploy next-generation voice models and workflow automation capabilities.
The technical challenge is significant: the company's current system is working well, but use cases are rapidly growing as the business expands beyond car insurance and new AI models emerge. You'll lead the charge in building the next-generation AI system to handle increasingly complex automations and enable bots to navigate external systems more quickly and accurately than human agents.
The tech stack includes TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda), and LLM models from OpenAI, Anthropic Claude, and Google Gemini.
REQUIREMENTS:
- 5+ years owning product strategy and execution for a technical product, ideally at an early-stage startup
- Hands-on experience working with engineering teams to make technical tradeoff calls
- Demonstrated ability to evaluate competing technical approaches based on business impact, not just technical elegance
- Experience tinkering with new AI models within days of release and explaining why one architecture or approach is superior
- Production experience with LLM-based systems, including evals, regressions, latency, cost, and failure-handling
Note: The company is hiring one person for this role and is flexible with job title/leveling based on the right candidate. Remote-first with optional offices in Palo Alto, New York City, Chicago, and Toronto. Hiring restrictions apply: must currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada.
