Principal Engineer (AI, Office of the CEO)

Jobber•Boston, MA

7d•Remote

About The Position

Jobber is seeking a Principal Software Engineer, AI, to join the Office of the CEO. This role is part of a startup within Jobber, a small, senior team tasked with reinventing how a 1,000-person company operates in the AI era. The team has the mandate and backing to implement significant changes, with direct access to decision-makers and a rapid development cycle. The work impacts every function at Jobber, shaping 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 aspects of AI implementation at scale, including trust, permissions, security, and quality. It offers significant autonomy and range, from designing novel system architectures to embedding with teams to deploy working AI solutions. The engineer will make strategic build-vs-buy decisions, conduct and terminate Proofs of Concept (POCs) efficiently, and establish the technical standards for all AI initiatives at Jobber. The ideal candidate has a proven history of 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.