Principal Engineer (AI, Office of the CEO)

Remote. Posted a month ago

The role

The Principal Software Engineer, AI will architect and build new internal AI systems from design to production. This founding technical role involves owning AI trust, permissions, security, and reliability while embedding with teams to ship AI into real workflows.

What you will do

Architect and build new internal AI systems end to end from first design to production
Own retrieval quality, permissions, security, and reliability for trustworthy AI at company scale
Work hands-on across the modern AI stack including LLMs, retrieval, agents, and integrations
Embed with teams across the company to ship AI into real workflows
Drive build-vs-buy evaluations and fast POCs
Work directly with executive leadership

Required qualifications

Track record of building production systems at Staff+ scope such as data infrastructure, retrieval, or applied AI used daily by hundreds to thousands of people
Hands-on depth with the modern AI stack
Founding-engineer, consulting, or forward-deployed experience
Daily working relationship with AI tools and agents
Communication skills to explain technical concepts to a CEO

Benefits

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
Access to coaching, learning, and leadership programs

About the company

Jobber is transforming the way service is delivered for small businesses like lawn care providers, home cleaning services, plumbers, or painters. They use technology to connect service providers with customers to help small businesses succeed.