Principal Engineer (AI, Office of the CEO)

This is a startup inside Jobber. A small, senior team in the Office of the CEO with a mandate to reinvent how a 1,000-person company operates in the AI era. Reporting to the VP of Customer Experience Innovation, the Principal Software Engineer will be the founding technical seat: you'll architect and build new AI systems from zero to production, and own the hard problems that come with putting AI at the center of how a company runs, including trust, permissions, security, and quality at scale.

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 foundations pragmatic; Embed with teams across the company, shipping AI into real workflows and leaving behind systems and owners that outlast the visit; Drive build-vs-buy evaluations and fast POCs, committing hard and killing fast; Work directly with executive leadership on what you build informs how the company makes decisions

Requirements

Track record of building production systems at Staff+ scope (data infrastructure, retrieval, or applied AI used daily by hundreds to thousands of people); Hands-on depth with the modern AI stack; At least one battle scar from a system that showed how confidently AI can be wrong; Pragmatic technology instincts, reaching for proven tools by default; Founding-engineer, consulting, or forward-deployed experience; Daily working relationship with AI tools and agents; Pragmatism to ship every few weeks, standards to make it trustworthy, and communication skills to explain both to a CEO

Benefits

Total compensation package including an extended health benefits package with fully paid premiums for both body and mind; Matching in RRSP, TFSA or FHSA; Stock options; Dedicated Talent Development team with access to coaching, learning, and leadership programs