Principal Engineer (AI, Office of the CEO)

Boston, 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 at company scale.

What you will do

Architect and build new internal AI systems end to end
Own retrieval quality, permissions, security, and reliability
Work hands-on across the modern AI stack
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
Hands-on depth with the modern AI stack
Pragmatic technology instincts
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 body and mind
Matching in RRSP, TFSA or FHSA
Stock options
Dedicated Talent Development team
Access to coaching, learning, and leadership programs
Annual stipends for health and wellness

About the company

Jobber is transforming the way service is delivered by connecting small businesses like lawn care providers and plumbers with their customers. The company uses technology to help tens of thousands of people save time and get paid.