Director, Software Engineering (AI Workflows & Ecosystem)
Jobber · Remote · Remote ·
COMPENSATION
€•• – ••k
Listed on the employer's job board (Ashby)
- Director level
- Fully remote
- AI & Agentic Systems
- Manage ~30 engineers
- Stock options included
Jobber helps small home service businesses manage their operations through technology. While AI features exist across the product, they remain fragmented. This role owns the shift from isolated AI features to a cohesive, intelligent system that proactively assists users.
You will lead approximately 30 engineers across four to six teams, reporting to senior engineering management. The focus is on building reliable agentic workflows, ensuring cross-product context, and establishing shared AI primitives for the entire organization.
What you'll do
- Define how AI functions across the entire product rather than within single teams
- Build and evolve a multi-team organization to execute the AI vision
- Make strategic tradeoffs between shipping speed, quality, and safety
- Drive adoption of AI systems across engineering, product, and the company
- Ensure AI output is reliable, measurable, and improves over time
- Establish shared AI primitives so teams do not reinvent solutions
What you'll need
- Experience managing managers across multiple engineering teams
- Proven track record building or leading production LLM or agentic systems
- Deep understanding of agent orchestration beyond simple prompt engineering
- Expertise in evaluation, observability, and failure handling for AI
- Ability to think in systems and understand end-to-end user workflows
- Experience driving cross-organizational alignment in ambiguous areas
Nice to have
- Background in balancing infrastructure needs with technical debt
- Experience partnering deeply with Product and Design teams
- Understanding of tradeoffs between autonomy and control in AI
Stack
- LLM
- Agentic Workflows
- AI Orchestration
- Copilot
- Voice Interfaces
- Messaging Systems
How you'll work
- Fully remote position
- Manage 4-6 Engineering Managers
- Oversee ~30 engineers across 4-6 teams
- Close partnership with Product and Design
What you get
- Extended health benefits with fully paid premiums
- RRSP, TFSA, or FHSA matching
- Stock options
- Access to coaching and leadership programs
- Dedicated Talent Development team