Remote AI Systems Architect — Scale LLMs & Automation

Jerry; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

PTO

Parental leave

401(k) match

Wellness benefits

Equity

Job summary

Jerry.ai is building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, became profitable, and now expand into home, motorcycle, RV, and beyond.

We’re a YC-backed, fully remote company with offices in Palo Alto, New York, Chicago, and Toronto, serving 5M+ customers. We’re seeking an engineering leader who can own the AI systems layer, drive production-grade LLM-based solutions, and set the bar for guardrails, latency, and cost as we scale to

Qualifications

• 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 evals, regressions, latency, cost, and failure handling

Responsibilities

• Decide what we build next in AI, and make the case for it. Nobody hands you a roadmap.
• 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.

Skills

3+ years product engineering

LLM production

systems thinking

problem solving

Job description

Jerry.ai is building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, became profitable, and now expand into home, motorcycle, RV, and beyond.

We’re a YC-backed, fully remote company with offices in Palo Alto, New York, Chicago, and Toronto, serving 5M+ customers. We’re seeking an engineering leader who can own the AI systems layer, drive production-grade LLM-based solutions, and set the bar for guardrails, latency, and cost as we scale to