Principal Engineer (AI, Office of the CEO)

Jobber

9d•$229,300 - $310,200

About The Position

This is a startup within Jobber, a small, senior team in the Office of the CEO tasked with reinventing how a 1,000-person company operates in the AI era. The team has the backing to achieve this goal, with direct access to decision-makers and a focus on rapid iteration and learning. The work impacts every function at Jobber and shapes how the company thinks and operates. The Principal Software Engineer will be the founding technical lead, responsible for architecting and building new AI systems from inception to production. This role involves owning critical challenges related to AI at the company's core, including trust, permissions, security, and quality at scale. It's a hands-on builder role with significant scope, involving system architecture design, embedding with teams to implement AI solutions, making build-vs-buy decisions, running and killing Proofs of Concept (POCs), and establishing technical standards for AI at Jobber. The ideal candidate has experience shipping production AI or data systems, prefers pragmatic technology choices, and desires founding-engineer ownership with substantial company resources.

Requirements

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.
Pragmatic technology instincts: you reach for proven tools by default and can defend the exceptions.
Founding-engineer, consulting, or forward-deployed experience: comfortable owning outcomes inside someone else's domain.
A daily working relationship with AI tools and agents, as instruments you build with and build for.
The pragmatism to ship every few weeks, the standards to make it trustworthy anyway, and the communication skills to explain both to a CEO.

Responsibilities

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.
Work hands-on across the modern AI stack (LLMs, retrieval, agents, integrations) while keeping the foundations deliberately pragmatic.
Embed with teams across the company, working day-to-day with function leaders and their teams and weekly with executive leadership, shipping AI into real workflows and leaving behind systems and owners that outlast the visit.
Drive build-vs-buy evaluations and fast POCs, with the judgment to commit hard and kill fast.
Work directly with executive leadership: what you build informs how the company makes decisions, every day.