Director, Software Engineering – AI Workflows, Ecosystem

Posted 2 weeks ago

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About the role

  • Director of Software Engineering overseeing AI workflows and ecosystem at Jobber. Leading system-level intelligence integrations across a product used by small service businesses.

Responsibilities

  • End-to-end ownership of Jobber’s AI system layer
  • Defining how AI should work across Jobber, not just within a team
  • Building and evolving a multi-team organization to execute the vision
  • Making tradeoffs between speed, quality, and safety
  • Encouraging a shift from feature thinking to system thinking across teams
  • Engaging with company leadership to challenge assumptions

Requirements

  • Proven leadership experience managing managers across multiple teams
  • Experience building organizations that scale, not just teams that ship
  • Ability to drive cross-org alignment in ambiguous spaces
  • Strong product and systems thinking, with an understanding of user workflows end-to-end
  • Deep partnership with Product and Design teams
  • Experience with production LLM/agentic systems

Benefits

  • Extended health benefits package with fully paid premiums for both body and mind
  • Matching in RRSP, TFSA or FHSA
  • Stock options
  • Dedicated Talent Development team and access to coaching, learning, and leadership programs
  • Unique opportunity to impact a $400-billion industry
  • Working with a supportive team that cares about customers

Job type

Full Time

Experience level

Lead

Salary

CA$221,800 - CA$300,100 per year

Degree requirement

No Education Requirement

Location requirements

RemoteCanada

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