Director, Software Engineering (AI Workflows & Ecosystem)

Jobber is dedicated to helping small businesses succeed through innovative technology solutions. The Director of Software Engineering will lead the transformation of Jobber’s AI capabilities, focusing on creating intelligent workflows and enhancing the overall system to proactively assist users in managing their businesses effectively.

Responsibilities:

• End-to-end ownership of Jobber’s AI system layer
• 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
• Push teams beyond feature thinking into system thinking
• Challenge assumptions, including leadership’s
• Drive adoption across engineering, product, and the company

Requirements:

• Experience building real systems where AI makes decisions and takes actions in production
• Experience with agent orchestration (not just prompts)
• Experience with tool use and workflow execution
• Experience with evaluation (offline + online)
• Experience with observability and failure handling
• Experience with guardrails and safety in real systems
• Experience with tradeoffs between autonomy vs. control
• Leadership experience managing managers across multiple teams
• Experience building organizations that scale (not just teams that ship)
• Experience driving cross-org alignment in ambiguous spaces
• Product and systems thinking, understanding how user workflows connect end-to-end
• Experience partnering deeply with Product and Design
• Focus on customer outcomes, not just technical output
• Experience with production LLM/agentic systems
• Understanding of what actually works in AI systems and what doesn't
• Experience improving systems that have failed
• Opinions about evaluation, reliability, and safety
• Ability to move fast without breaking everything
• Experience balancing shipping vs infrastructure vs tech debt
• Knowledge of when to iterate and when to redesign