Director, Software Engineering (AI Workflows & Ecosystem)
Jobber · Remote · Remote ·
COMPENSATION
€•• – ••k
Listed on the employer's job board (Ashby)
- Director level leadership
- Fully remote role
- Manage ~30 engineers
- AI agentic systems
- CAD salary provided
You will own the end-to-end AI system layer at Jobber, transforming fragmented tools into proactive business operations. Leading approximately 30 engineers across four to six teams, you will define how intelligence flows across the entire product to help service professionals automate decisions and actions.
This position requires deep expertise in production LLM and agentic systems, focusing on orchestration, evaluation, and safety. You will partner closely with Product and Design to ensure AI removes cognitive load for users rather than just adding features.
What you'll do
- Define how AI functions across the entire product ecosystem
- Build and evolve a multi-team organization to execute vision
- Make tradeoffs between shipping speed, quality, and safety
- Drive adoption of AI systems across engineering and product
- Ensure reliability, safety, and proper failure handling
- Establish shared AI primitives to prevent reinvention
- Challenge assumptions and push for system-level thinking
What you'll need
- Experience managing managers across multiple teams
- Built or led production LLM and agentic systems
- Deep understanding of agent orchestration and tool use
- Expertise in offline and online evaluation methods
- Proven ability to drive cross-org alignment in ambiguity
- Strong grasp of observability and failure modes in AI
- Ability to reason at the system level without daily coding
Stack
- LLM
- Agentic workflows
- AI orchestration
- Copilot
- Automations
How you'll work
- Fully remote position
- Reports to senior leadership
- Manages 4-6 Engineering Managers
What you get
- Extended health benefits with paid premiums
- RRSP, TFSA, or FHSA matching contributions
- Stock options included in compensation
- Access to coaching and leadership programs
- Transparent and fair compensation structure