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Jerry is a YC-backed, profitable Series C startup with 5M+ customers building the first AI-powered advisor to manage physical assets (cars, homes, motorcycles, RVs, boats). The company has pioneered AI-driven automation for sales and service conversations, handling 70% of inbound requests—over 50,000 chats monthly in production.
As Senior AI Systems Architect, you'll own the AI systems layer of a consumer product used by millions. The role focuses on the infrastructure around LLMs and agents: defining what agents are allowed to do, designing guardrails, establishing evaluation frameworks, and determining what "correct" means in non-deterministic outputs.
Key responsibilities include: deciding what to build next in AI and making the case for it; partnering with OpenAI to evaluate and deploy next-generation voice models and workflow automation; evaluating emerging technologies (voicebot, computer use agents); designing evaluation frameworks and making tradeoffs between latency, cost, and accuracy in regulated production environments; setting technical standards for chatbot systems; building new automations (record disputes, email/callout reduction, document validation); and working with subject matter experts to turn domain knowledge into production systems.
You'll work in a flat organization with direct access to founders and executives. The technical challenges center on production-grade LLM systems: evals, regressions, latency optimization, cost management, and failure handling. This is hands-on architecture work, not just strategy—you'll prototype emerging technologies and make investment decisions based on real validation.
Ideal candidates have 5+ years in product or forward-deployed engineering at early-stage startups, a track record of turning ambiguous problems into scalable systems, and hands-on experience deploying LLM-based systems to production including the unglamorous operational aspects.
