AI Systems Architect

Jerry.ai•New York, NY

3d•$130,000 - $170,000•Remote

About The Position

Join a YC-backed, profitable Series C startup with capital and over 5M+ customers. This role involves owning the AI systems layer of a consumer product used by millions, focusing on LLMs, agents, and internal APIs applied to a fragmented $2T market. You will work with partners like OpenAI to integrate Jerry.ai services directly into the ChatGPT App and pioneer new model capabilities. The company offers a flat organization, ambitious goals, and a direct line to the founders and execs. The technical challenge lies in building the system around AI, including agent capabilities, system integration, guardrails, and handling non-deterministic outputs. Jerry is building the first AI-powered advisor to manage all physical assets, starting with cars and expanding into new verticals like home, motorcycle, RV, and boat. The company has a proven track record with its own infrastructure automating sales and service conversations, handling over 50,000 chats a month. This role requires someone to run a fast-moving, high-volume chatbot operation and have a strong point of view on future AI bets like voicebot, computer use, and consumer AI applications.

Requirements

A systems designer. You think in interfaces, failure modes, and blast radius. You've been the person who redesigned something messy rather than working around it.
Fluent in modern AI. You read the release notes when a new model drops and you've already built something with it. You have opinions about eval design, and they came from doing it.
Pragmatic. You know when to build the durable thing and when to ship the version that works this quarter.
3+ years in a product engineering or forward deployed engineering, ideally in an early stage startup
A track record of turning ambiguous problems into systems that actually run
Hands-on experience putting LLM-based systems into production, including the unglamorous parts: evals, regressions, latency, cost, and failure handling

Responsibilities

Decide what we build next in AI, and make the case for it.
Partner with OpenAI to evaluate and deploy next-generation voice models and workflow automation.
Evaluate emerging AI technology (voicebot, computer use agents, and beyond), prototype what's worth building, and make the call on what we invest in next.
Design evaluation frameworks and guardrails, and make the real tradeoffs between latency, cost, and accuracy in a regulated production environment.
Set the technical bar for our chatbot systems — shape what the prompt engineering team builds next and keep the architecture sound as it scales.
Build new automations across areas like record disputes, email/callout reduction, document validation (ex. licenses, proof of insurance).
Work directly with subject matter experts to turn domain knowledge into systems that behave correctly.