Senior AI Systems Architect

• Join a YC-backed profitable Series C startup with capital with 5M customers

• Own the AI systems layer of a consumer product used by millions LLMs agents and internal APIs applied to a fragmented $2T market.

• Work with partners like OpenAI to integrate services directly into the ChatGPT App and pioneer new model capabilities.

• Flat org ambitious goals and a direct line to the founders and execs.

The interesting problems arent in the prompt anymore. Theyre 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 isnt deterministic.

We are building the first AI-powered advisor to manage all your physical assets. We started with the car in 2019 now were 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 50000 chats a month in production at scale.

That head start gave us real leverage and its 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.

• 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 whats 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.

• 5 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

While we appreciate your interest and application due to the volume of applications we receive only applicants under consideration will be contacted.

Please note: 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.

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.

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 candidates starting pay will fall within the pay range listed on this job posting determined based on job-related factors including but not limited to skills experience qualifications work location and market conditions. Ranges are market-dependent and may be modified in the addition to base salary the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees including health dental and vision coverage paid time off paid parental leave 401(K) plan with employer matching and wellness benefits among others. Equity opportunities may also be part of your total rewards package. Part-time contract or freelance roles may not be eligible for certain benefits.

About

Your car and your home are your most expensive assets. And for most people these arent just purchases theyre the physical embodiment of the life youve worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey buying insuring maintaining repairing selling is fragmented complicated and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price lock in the best insurance rate without you lifting a finger remind you before that service appointment turns into an expensive repair or worse an accident and help you sell at the best price when the time is right. That friend is Jerry.

Jerry is building the first AI agent to manage all your physical assets. We started with car insurance in 2019 became one of the top 3 brokers in the U.S. then added driving insights diagnostics and a repair marketplace.

Weve reached 5M customers raised $240M and have been profitable since 2024. Were now expanding into home motorcycle RV and beyond.

Were fully remote with offices in Palo Alto New York Chicago and Toronto.

Required Experience:

Senior IC