Principal Engineer (AI, Office of the CEO)

Stack

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) with deliberately pragmatic foundations
• ▹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

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, and at least one battle scar from a system that showed how confidently AI can be wrong
• ▹Pragmatic technology instincts: proven tools by default, able to defend the exceptions
• ▹Founding-engineer, consulting or forward-deployed experience: comfortable owning outcomes inside someone else's domain
• ▹Daily working relationship with AI tools and agents, as instruments you build with and build for

Soft skills

What we offer

• ▹Extended health benefits with fully paid premiums for body and mind
• ▹Matching in RRSP, TFSA or FHSA
• ▹Stock options
• ▹Dedicated Talent Development team

About the company

Jobber is a company of about 1,000 people. A small senior team in the Office of the CEO has a mandate to reinvent how the company operates in the AI era.