Director of Software Engineering (AI Workflows & Ecosystem)

Join Jobber as the Director of Software Engineering, where you will have end-to-end ownership of the AI system layer. You will be responsible for how decisions are made inside the system, how context moves across workflows, and how actions are triggered. You will lead a team of ~30 engineers across 4-6 teams and work closely with Product, Design, and Data. Your focus will be on building systems that remove thinking from overwhelmed people and drive adoption across engineering, product, and the company.

• End-to-end ownership of Jobber’s AI system layer, ensuring intelligence flows across the entire product.
• Defining how AI should work across Jobber, building and evolving a multi-team organization to execute on that vision.
• Driving adoption across engineering, product, and the company, ensuring customers feel like the product is working for them.
• Customers feel like the product is working for them, not just responding
• Engineers trust the system, and move faster because of it
• Instead:
• The system proactively recommends and takes actions
• AI output is reliable, measurable, and improving over time
• Not “we shipped AI features.”
• Teams build on shared AI primitives, not reinventing them
• Built real systems where AI makes decisions and takes actions in production
• Observability and failure handling
• Agent orchestration (not just prompts)
• Tool use and workflow execution
• Evaluation (offline + online)
• You don’t need to code daily, but you must be able to reason at the system level
• Guardrails and safety in real systems
• Tradeoffs between autonomy vs. control
• You understand how user workflows connect end-to-end
• You care about customer outcomes, not just technical output
• You’ve led orgs through complexity, not just growth
• You can move fast without breaking everything
• Managed managers across multiple teams
• Driven cross-org alignment in ambiguous spaces
• You understand what actually works (and what doesn’t)
• You think in systems, not features
• You’ve balanced shipping vs infrastructure vs tech debt
• You know when to iterate and when to redesign
• You’ve partnered deeply with Product and Design
• You’ve built or led production LLM/agentic systems
• You have opinions about evaluation, reliability, and safety
• Built organizations that scale (not just teams that ship)
• You’ve seen systems fail and improved them