SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
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. Currently, 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 that powers Jerry's core product—the insurance marketplace. This includes two critical components: (1) the agentic/conversational front end (chatbot, voicebot, computer-use agents) where you'll shape the prompt engineering team's direction and maintain architectural soundness at scale, 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:
- Architect and lead the next-generation AI system as the company expands beyond car insurance and AI models evolve
- Evaluate emerging AI technologies (voicebot, computer-use agents, and beyond) and make investment decisions
- Build new automations for document validation, stateful phone-based voicebot interactions, and direct external system navigation to resolve complex issues faster and more accurately than human agents
- Partner with OpenAI to evaluate and deploy next-generation voice models and workflow automation
- Own outcomes end-to-end, from design through production deployment
The role requires deep expertise in production LLM systems, including the unglamorous but critical aspects: evaluations, regression testing, latency optimization, cost management, and failure handling. You'll work with a tech stack including TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda), and LLM models from OpenAI, Anthropic Claude, and Google Gemini.
Jerry is remote-first but offers hybrid and in-person options at offices in Palo Alto, New York City, Chicago, and Toronto. The company is led by serial entrepreneurs and backed by Y Combinator, with a team drawn from Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Jerry consistently ranks among Y Combinator's Top Companies and Forbes/Statista's Best Startup Employers.
REQUIREMENTS:
- 5+ years of software engineering experience, ideally at an early-stage startup where you owned outcomes end-to-end
- Proven ability to tinker with new models within days of release and explain why one architecture or approach is superior to another
- Hands-on experience putting LLM-based systems into production, including evals, regressions, latency, cost, and failure-handling
- Builder mentality; you don't need someone else to write the spec
- Must currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada (full-time salaried employees)
