Principal Engineer (AI, Office of the CEO)

Startup inside Jobber in the Office of the CEO, a small senior team with a mandate to reinvent how a 1,000-person company operates in the AI era. The Principal Software Engineer, AI will be the founding technical seat, reporting to the VP of Customer Experience Innovation, building new AI systems from zero to production and owning 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 deliberately 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, with the judgment to commit hard and kill fast; Work directly with executive leadership, informing 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 and defending 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 to build with and build for; 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 equity rewards; Annual stipends for health and wellness; Retirement savings matching (RRSP, TFSA or FHSA); Extended health benefits package with fully paid premiums for both body and mind; Stock options; Dedicated Talent Development program with career coaching, learning, and leadership programs