Remote Director, AI Systems & Workflow Orchestration

Octopusapp Inc.; United States; On-site; USD 230,000 - 320,000; Full time

Job summary

Jobber seeks a Director of Software Engineering to own AI workflows and the ecosystem, leading a multi-team effort across product, design, and data. This role will shape how intelligence flows through the platform, aligning engineering with business outcomes and customer value.

You’ll drive end-to-end AI system design, establish guardrails, and foster a scalable organization that delivers reliable, measurable AI capabilities for tens of thousands of service businesses.

Qualifications

• Led orgs through complexity and built scalable organizations.
• Think in systems; connect end-to-end user workflows.
• Balance shipping with infrastructure and tech debt; execute fast without breaking everything.

Responsibilities

• 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 trade-offs between speed, quality, and safety.
• Push teams beyond feature thinking into system thinking.
• Drive adoption across engineering, product, and the company.

Skills

Leadership

Systems thinking

Execution

Job description

Jobber seeks a Director of Software Engineering to own AI workflows and the ecosystem, leading a multi-team effort across product, design, and data. This role will shape how intelligence flows through the platform, aligning engineering with business outcomes and customer value.

You’ll drive end-to-end AI system design, establish guardrails, and foster a scalable organization that delivers reliable, measurable AI capabilities for tens of thousands of service businesses.