Director, Software Engineering (AI Workflows & Ecosystem)
About this role
The Director, Software Engineering (AI Workflows & Ecosystem) position is a remote role focused on leading the overarching artificial intelligence system layer to transform small service businesses. This opportunity suits an experienced engineering leader who specializes in production-grade AI agent systems, multi-team management, and end-to-end product intelligence.
Role Overview
This role takes full ownership of Jobber's centralized artificial intelligence strategy, moving the platform beyond fragmented features into fully realized intelligent business operations. The position manages approximately thirty engineers spanning four to six teams through four to six engineering managers and senior engineering managers. Collaboration happens closely with product, design, and data departments to unify intelligence across jobs, customer management, payments, and communications.
Key Responsibilities
Requirements
Skills and Tools
Salary and Benefits
The salary range for this remote position spans a minimum annual salary of $221,800 CAD, a midpoint of $261,000 CAD, and a maximum salary of $300,100 CAD. Additional benefits include a comprehensive extended health benefits package with fully paid premiums, matching contributions for RRSP, TFSA, or FHSA, stock options, and access to a dedicated Talent Development team for coaching and leadership programs.
About the Company
Jobber provides technology to help small home service businesses, such as plumbers, painters, and landscapers, manage quoting, scheduling, invoicing, and customer payments. The platform currently supports over 250,000 businesses and features live capabilities like the AI Receptionist alongside various embedded product features.
How to Apply
Interested candidates should apply on the official company careers page.
Skills and tech stack
Questions candidates ask
What is the primary objective of this director role?
The director owns the end-to-end AI system layer to evolve the platform from fragmented AI features into unified, AI-powered business operations that proactively assist small service businesses.
What team size and structure will report to this position?
The role oversees approximately 30 engineers organized into 4 to 6 teams, with 4 to 6 engineering managers or senior engineering managers reporting directly to the director.
What kind of AI background is required for this job?
Candidates must have hands-on experience building real production systems where AI makes decisions and takes actions, including agent orchestration, tool use, evaluation, observability, and safety guardrails.
What is the salary range for this role?
The annual salary ranges from a minimum of $221,800 CAD to a maximum of $300,100 CAD, with a midpoint of $261,000 CAD.
Where is the position located?
The position is fully remote.