About The Position

You will lead the evolution of our AI-powered customer experience and internal AI platform. Your challenge will be to own one of the most strategic areas of the company: how we leverage large language models, agents, and internal APIs to deliver best-in-class, automated customer support and operations. You will sit at the intersection of product, engineering, and applied AI , and require both strategic thinking and hands-on exploration with modern LLM systems. You will build and scale a sophisticated AI system that already includes: A production-grade conversational AI experience automating >70% of inbound sales and service over chat and SMS Human-in-the-loop systems for chat evaluation, feedback, and continuous improvement Internal process automation flows across the company, including automated image review and approval Jerry.ai insurance and repair quotes available directly in the ChatGPT App, developed in partnership with OpenAI You will also be responsible for constantly evaluating new models and AI capabilities. This includes evaluating emerging AI technologies, such as voice models and computer use agents, for suitability in a regulated production environment.

Requirements

  • You have 4+ years of experience in technical product management, management consulting, data analytics, or operations at a fast-paced startup.
  • You're passionate about AI and intrinsically motivated to get hands on with the latest technology. When a new model drops, you read the release notes. You've set up your own AI tools and workflows not because someone told you to, but because you couldn't help yourself.
  • You're a technologist and a systems thinker . You're comfortable in technical conversations about system architecture, API design, and prompt engineering, and you can translate complex ideas into simple terms for non-technical stakeholders.
  • You're data-driven , familiar with SQL, and comfortable diving into data to answer your own questions.
  • You like to own metrics and constantly seek improvement .
  • You're an optimist who asks "how can we" not "if we can."

Responsibilities

  • Lead end-to-end product development for Jerry's AI-powered customer experiences and internal AI platform, from roadmap to rollout.
  • Partner with engineers and prompt engineers to design and iterate on AI architectures, prompt strategies, evaluation frameworks, and guardrails — making real tradeoffs between latency, cost, accuracy, and user experience.
  • Be the bridge between engineering and the rest of the org: lead by example for AI best practices and get other teams on board with platform standards.
  • Own the metrics that matter — answer quality, customer satisfaction, automation rate, escalation quality — and drive systematic improvement through data and experimentation.
  • Work directly with our partners at OpenAI to evaluate new models and capabilities, and identify the next big leaps in voice, computer use, and workflow automation.

Benefits

  • 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.
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