Principal AI Engineer (Office of the CEO)

Join Jobber as a Principal AI Engineer, where you'll be the founding technical seat in the Office of the CEO. You'll architect and build new AI systems from scratch, tackle challenges related to trust, permissions, security, and quality at scale. This role offers a unique range of responsibilities, from designing system architecture to embedding with teams and shipping AI into real workflows. You'll also drive build-vs-buy evaluations and work directly with executive leadership. Ideal candidates have a track record of building production systems, hands-on experience with the modern AI stack, and strong communication skills.

- Architect and build new internal AI systems end to end, from first design to production, as the founding engineer. - Own the hard parts of trustworthy AI at company scale: retrieval quality, permissions, security, and reliability. - Drive build-vs-buy evaluations and fast POCs, with the judgment to commit hard and kill fast.

- A track record of building production systems at Staff+ scope: data infrastructure, retrieval, or applied AI used daily by hundreds to thousands of people who depend on it - Hands-on depth with the modern AI stack, and at least one battle scar from a system that showed you how confidently AI can be wrong - The pragmatism to ship every few weeks, the standards to make it trustworthy anyway, and the communication skills to explain both to a CEO - A daily working relationship with AI tools and agents, as instruments you build with and build for - Founding-engineer, consulting, or forward-deployed experience: comfortable owning outcomes inside someone else's domain - Pragmatic technology instincts: you reach for proven tools by default and can defend the exceptions