Director, Software Engineering – AI Workflows, Ecosystem

This is a fully remote position, open to applicants in Canada.

📋 Description

• Complete ownership of Jobber’s AI system layer from start to finish.

• Establishing how AI should function throughout Jobber, not limited to a single team.

• Developing and enhancing a multi-team structure to realize the vision.

• Balancing tradeoffs between speed, quality, and safety.

• Promoting a transition from feature-focused thinking to system-oriented thinking across teams.

• Collaborating with company leadership to challenge existing assumptions.

⛳️ Requirements

• Demonstrated leadership experience in managing managers across various teams.

• Experience in creating organizations that scale rather than just teams that deliver.

• Capability to foster cross-organizational alignment in uncertain environments.

• Strong product and systems thinking, with a comprehensive understanding of user workflows from beginning to end.

• Deep collaboration with Product and Design teams.

• Experience with production-level LLM/agentic systems.

🏝️ Benefits

• Comprehensive health benefits package with fully covered premiums for both physical and mental well-being.

• Matching contributions in RRSP, TFSA, or FHSA.

• Stock options available.

• Access to a dedicated Talent Development team along with coaching, learning, and leadership programs.

• Unique opportunity to make a significant impact in a $400-billion industry.

• Being part of a supportive team that prioritizes customer care.