Director, AI Systems & Workflow Orchestration

Jobber; United States; Remote; USD 157,000 - 212,000; Full time

Benefits offered by this job

Health benefits

Stock options

RRSP/TFSA/ FHSA matching

Job summary

Jobber is seeking a Director of AI to own the company’s AI system layer end-to-end. You’ll oversee approximately 30 engineers across 4–6 teams and partner with Product, Design, and Data to deliver system-wide AI that reduces cognitive load for customers.

You’ll shape governance, guardrails, and observability while pushing for reliable, measurable improvements in AI-driven workflows and business operations. This is a leadership role with a strong compensation framework and growth opportunities.

Qualifications

• Leadership experience building and scaling organizations.
• System thinking across end-to-end product workflows.
• Proven track record with production AI/LLM systems.
• Ability to balance speed, quality, and safety in delivery.

Responsibilities

• Define how AI should work across Jobber, not just within a team.
• Build and evolve a multi-team org to execute on that vision.
• Make tradeoffs between speed, quality, and safety.
• Drive adoption of AI across engineering, product, and the company.

Skills

Leadership

Product thinking

AI depth

Execution

Job description

Jobber is seeking a Director of AI to own the company’s AI system layer end-to-end. You’ll oversee approximately 30 engineers across 4–6 teams and partner with Product, Design, and Data to deliver system-wide AI that reduces cognitive load for customers.

You’ll shape governance, guardrails, and observability while pushing for reliable, measurable improvements in AI-driven workflows and business operations. This is a leadership role with a strong compensation framework and growth opportunities.