Principal Engineer (AI, Office of the CEO)
Jobber · USA
About this role
## Overview Do you want to be the first engineer on something an entire company will run on? Jobber is looking for a **Principal Software Engineer, AI** to join the **Office of the CEO**. > **Note:** Our Talent team will be offline for **Jobber Impact** (Oct 6–Oct 9). We’ll review applications and follow up after we return next week. This message is automatically updated on job posts above the “What you can expect from Jobber” section. --- ## The Team This is a startup inside Jobber: a **small, senior team** with a mandate to reinvent how a **1,000-person company** operates in the AI era. You’ll have **no layers between you and decision-makers**, no “roadmap theater,” and you’ll ship real work frequently—**learn, compound, and move fast**. Your work touches every function at Jobber, and what you build becomes how the company thinks and moves. --- ## The Role Reporting to the **VP of Customer Experience Innovation**, you’ll be the **founding technical seat**—architecting and building new AI systems **from zero to production**. You’ll own the hard problems of putting AI at the center of how a company runs, including: - **Trust** - **Permissions** - **Security** - **Quality at scale** This is a builder’s role with unusual range: one week you may design architecture for something new; the next you’ll embed with teams, ship working AI into real workflows, and make them successful. You’ll make **build-vs-buy** decisions, run **POCs** (and kill them quickly when needed), and set the technical standards for all AI work at Jobber. --- ## What You’ll Do - Architect and build new internal AI systems **end to end** (design → production) as the founding engineer - Own the hard parts of trustworthy AI at company scale (e.g., **retrieval quality, permissions, security, reliability**) - Work hands-on across the modern AI stack (**LLMs, retrieval, agents, integrations**) while keeping foundations pragmatic - Embed with teams across the company, shipping AI into real workflows and leaving behind systems and owners - Drive **build-vs-buy** evaluations and fast POCs with strong judgment - Partner directly with executive leadership—what you build informs company decisions --- ## What You Bring - Proven experience building **production systems** at **Staff+ scope** (data infrastructure, retrieval, or applied AI used daily by hundreds to thousands) - Hands-on depth with the modern AI stack, plus experience learning from systems that can be wrong - Pragmatic technology instincts: default to proven tools and defend exceptions - Founding-engineer / consulting / forward-deployed experience: comfortable owning outcomes in someone else’s domain - A daily working relationship with AI tools and agents (as instruments you build with and for) - Ability to ship every few weeks while maintaining standards for trustworthiness - Strong communication skills (including explaining to a CEO) --- ## Compensation Jobber is committed to transparent, fair compensation. - **Minimum:** $229,300 - **Midpoint:** $269,700 - **Maximum:** $310,200 Total compensation also includes **equity rewards**, **annual health & wellness stipends**, **retirement savings matching**, and an **extended health package** with fully paid premiums for **body and mind**. --- ## What You Can Expect from Jobber - Extended health benefits with fully paid premiums (body & mind) - Matching in **RRSP, TFSA, or FHSA** - Stock options - Dedicated Talent Development team, including coaching and lea
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