SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Jerry.ai is a pre-IPO insurtech startup that has raised $240M, serves 5M+ customers, and is profitable. 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 of Jerry's customer-facing Agentic AI product, which already automates over 70% of inbound sales and service requests (50k+ chats monthly). This role sits at the intersection of product, engineering, and applied AI, reporting directly to the COO.
Key responsibilities:
- Own end-to-end development of the AI platform and customer experiences, from roadmap through rollout
- Partner with engineering to design prompt strategies, evaluation frameworks, and guardrails that balance latency, cost, and accuracy
- Act as technical translator between engineering and the broader organization, establishing AI best practices and platform standards
- Drive systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation
- Collaborate with OpenAI partners to evaluate and deploy next-generation voice models and workflow automation capabilities
- Consolidate fragmented AI infrastructure (currently spread across six locations) into a unified platform with clear ownership
You are a technologist deeply familiar with modern LLMs and agentic systems. You think in systems, are comfortable with technical architecture discussions, and can translate complex AI concepts for any audience. You have hands-on experience with SQL, data analysis, and building custom AI workflows. You're pragmatic about technical tradeoffs and lead by example.
Ideal background: 4+ years in technical roles such as forward-deployed engineering, technical product management, or similar at fast-paced startups. You have a track record of turning complex strategic ideas into scalable, production-grade products.
