AI Systems Architect
Why you should join us?
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Join a YC-backed, profitable Series C startup with capital with 5M+ customers
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Own the AI systems layer of a consumer product used by millions — LLMs, agents, and internal APIs applied to a fragmented $2T market.
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Work with partners like OpenAI to integrate Jerry .ai services directly into the ChatGPT App and pioneer new model capabilities.
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Flat org, ambitious goals, and a direct line to the founders and execs.
The technical challenge:
The interesting problems aren't in the prompt anymore. They're in the system around it: what the agents are allowed to do, how the pieces fit together, where the guardrails go, and what 'correct' even means when the output isn't deterministic.
We are building the first AI-powered advisor to manage all your physical assets. We started with the car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.
Before off-the-shelf platforms existed, we built our own infrastructure to automate sales and service conversations. That system now handles over 70% of inbound sales and service requests: more than 50,000 chats a month, in production, at scale.
That head start gave us real leverage, and it's outgrown ad hoc ownership. We need someone who can run a fast-moving, high-volume chatbot operation day to day and has a real point of view on the next bets: voicebot, computer use, consumer AI applications.
What you'll actually do:
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Decide what we build next in AI, and make the case for it. Nobody hands you a roadmap.
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Partner with OpenAI to evaluate and deploy next-generation voice models and workflow automation.
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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.
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Design evaluation frameworks and guardrails, and make the real tradeoffs between latency, cost, and accuracy in a regulated production environment.
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Set the technical bar for our chatbot systems — shape what the prompt engineering team builds next and keep the architecture sound as it scales.
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Build new automations across areas like record disputes, email/callout reduction, document validation (ex. licenses, proof of insurance).
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Work directly with subject matter experts to turn domain knowledge into systems that behave correctly.
Ideal experience:
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3+ years in a product engineering or forward deployed engineering, ideally in an early stage startup
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A track record of turning ambiguous problems into systems that actually run
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Hands-on experience putting LLM-based systems into production, including the unglamorous parts: evals, regressions, latency, cost, and failure handling
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry .ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry .ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry .ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at
The successful candidate’s starting pay will fall within the pay range listed on this job posting, de