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Jerry.ai is a pre-IPO insurtech startup that has raised $240M and achieved profitability with 5M+ customers. The company is building an AI-powered platform to manage the entire car and home ownership experience—from buying/selling to insurance, maintenance, and repairs.
You will lead the development and scaling of Jerry.ai's customer-facing AI agents and automation platform. The system currently automates over 70% of inbound sales and service requests (50k+ chats monthly) using homegrown generative AI infrastructure built before off-the-shelf platforms existed. However, the underlying prompts and systems are fragmented across six separate locations with no unified platform or single source of truth.
In this role, you will own the consolidation and evolution of this AI infrastructure. You'll sit at the intersection of product, engineering, and applied AI, responsible for:
- Leading end-to-end development of the AI platform and customer experiences from roadmap through rollout
- Partnering with engineers to design prompt strategies, evaluation frameworks, and guardrails that balance latency, cost, and accuracy
- Serving as the technical translator between engineering and the broader organization, establishing AI best practices and platform standards
- Driving systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation
- Collaborating with OpenAI partners to evaluate and deploy next-generation voice models and workflow automation capabilities
You'll report directly to the COO and lead one of the company's most important growth levers. The ideal candidate has 3+ years in a technical role (forward-deployed engineering, technical product management, or similar) at a fast-paced startup, deep passion for AI systems and modern LLMs, and a track record of turning complex strategic ideas into scalable, production-grade products. You should be comfortable with SQL, system architecture discussions, and navigating technical tradeoffs pragmatically.
