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
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