Director, Software Engineering (AI Workflows & Ecosystem)

Stack

Responsibilities

• ▹Define how AI should work across Jobber, not just within a single team
• ▹Build and evolve a multi-team organization (~30 engineers, 4-6 teams, 4-6 EMs/Sr EMs) to execute the vision
• ▹Balance tradeoffs between speed, quality, and safety
• ▹Push teams from feature thinking to system thinking
• ▹Partner closely with Product, Design, and Data
• ▹Own agentic workflows (reason → decide → act → evaluate), cross-product context, reliability, and guardrails

Requirements

• ▹Proven leadership experience managing complexity, not just growth
• ▹Experience managing managers across multiple teams
• ▹Track record building organizations that scale
• ▹Strong systems thinking and understanding of end-to-end user workflows
• ▹Deep partnership experience with Product and Design
• ▹Experience building or leading real, production AI/agentic systems (not just using LLM APIs for features)
• ▹Experience with agent orchestration, tool use, workflow execution, evaluation (offline and online), observability, and failure handling

Soft skills

What we offer

• ▹Extended health benefits with fully paid premiums (body and mind)
• ▹RRSP, TFSA, or FHSA matching
• ▹Stock options
• ▹Dedicated Talent Development team with coaching and leadership programs

About the company

Jobber is a software platform that helps small home-service businesses — plumbers, painters, landscapers, and more — quote, schedule, invoice, and collect payments. With 250,000+ businesses on the platform, the company's goal is to evolve the entire product into one unified, intelligent system powered by AI.