Principal Engineer, AI

. Architect and build new internal AI systems end to end, from initial design through production .

Posted 9/25/2026full-timeBoston • Massachusetts • United StatesLead💰 $229,300 - $310,200 per yearWebsite

Key responsibilities & impact

Architect and build new internal AI systems end to end, from initial design through production
Own retrieval quality, permissions, security, and reliability for trustworthy AI at company scale
Work hands-on across LLMs, retrieval, agents, and integrations
Embed with teams across the company and function leaders to ship AI into real workflows
Collaborate weekly with executive leadership
Leave behind systems and owners that outlast embedded engagements
Drive build-versus-buy evaluations and rapid proofs of concept
Make technical decisions that inform how Jobber operates and makes decisions

What you’ll need

Track record of building production systems at Staff+ scope, including data infrastructure, retrieval, or applied AI used daily by hundreds to thousands of people
Hands-on depth with the modern AI stack
Experience with production AI or data systems
Experience with LLMs, retrieval, agents, and integrations
Pragmatic technology instincts and ability to justify technology choices
Founding-engineer, consulting, or forward-deployed experience
Comfortable owning outcomes inside another team's domain
Daily working relationship with AI tools and agents
Ability to ship every few weeks while maintaining trustworthy systems
Communication skills to explain technical decisions to a CEO
Must be legally entitled to work in the US
Must be based in the Boston area and able to attend the office at least 1 day per week
Must be comfortable attending one in-person interview at the nearest Jobber office

Comp & perks