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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 car ownership—from buying and selling to insurance, maintenance, and repairs. Jerry launched as a top-three car insurance broker in the US and has been an early adopter of generative AI, building proprietary infrastructure to automate customer interactions.
You will lead the development and scaling of Jerry's AI agents and automation platform, which currently handles over 70% of inbound sales and service requests (50k+ chats monthly). This is a strategic, high-impact role sitting at the intersection of product, engineering, and applied AI. You will report directly to the COO and own the roadmap for next-generation capabilities including voicebot, computer-use agents, and consumer AI applications.
Key responsibilities include:
- End-to-end ownership of the AI platform roadmap, from conception through production rollout
- Designing prompt strategies, evaluation frameworks, and safety guardrails in collaboration with engineering
- Serving as the technical bridge between engineering and the broader organization, establishing AI best practices and platform standards
- Driving systematic improvements in answer quality, customer satisfaction, and automation rates through rigorous experimentation and data analysis
- Partnering with OpenAI to evaluate and deploy next-generation voice models and workflow automation capabilities
You are a technologist deeply familiar with modern LLMs and AI systems, with hands-on experience building custom workflows. You think in systems and can navigate complex technical tradeoffs while translating them for non-technical stakeholders. You are data-driven, comfortable with SQL, and pragmatic about implementation. You have 3+ years in a technical role such as forward-deployed engineering or technical product management at a fast-paced startup, with a proven track record of turning complex strategic ideas into scalable, production-grade products.
