Director, Software Engineering

About the Company

Jobber exists to help people in small businesses be successful. We work with small home service businesses, like your local plumbers, painters, and landscapers, to transform the way service is delivered through technology.

Responsibilities

• Define how AI should work across Jobber, not just within a team
• Build and evolve a multi-team org to execute on the vision
• Own end-to-end Jobber’s AI system layer, including foundations, copilot, and automations
• Make tradeoffs between speed, quality, and safety
• Push teams beyond feature thinking into system thinking
• Drive adoption across engineering, product, and the company

Requirements

• Experience managing managers across multiple teams
• Proven track record of building and leading production LLM/agentic systems
• Deep understanding of agent orchestration, tool use, and workflow execution
• Experience with AI evaluation, observability, and safety guardrails
• Strong product and systems thinking skills
• Ability to lead organizations through complexity and drive cross-org alignment

Benefits

• Extended health benefits package with fully paid premiums
• RRSP, TFSA, or FHSA matching
• Stock options
• Access to coaching, learning, and leadership programs