Note: The job is a remote job and is open to candidates in USA. Jobber is a company dedicated to helping small businesses succeed through innovative technology solutions. They are seeking a Director of Software Engineering to lead the development of AI-powered workflows and business operations, ensuring that AI systems work seamlessly across their product to enhance customer experiences.
Responsibilities
- End-to-end ownership of Jobber’s AI system layer
- Define how AI should work across Jobber, not just within a team
- Build and evolve a multi-team org to execute on that vision
- Make tradeoffs between speed, quality, and safety
- Push teams beyond feature thinking into system thinking
- Challenge assumptions, including leadership’s
- Drive adoption across engineering, product, and the company
- How decisions get made inside the system
- How context moves across workflows
- How actions get triggered (and when they shouldn’t)
- How we evaluate whether AI is actually working
- Agentic workflows (reason → decide → act → evaluate)
- Cross-product context (jobs, customers, payments, communication)
- Reliability, safety, and failure modes
- Developer experience for building on top of AI systems
Skills
- Built real systems where AI makes decisions and takes actions in production
- Experience with agent orchestration (not just prompts)
- Experience with tool use and workflow execution
- Experience with evaluation (offline + online)
- Experience with observability and failure handling
- Experience with guardrails and safety in real systems
- Understanding of tradeoffs between autonomy vs. control
- Leadership experience managing managers across multiple teams
- Experience building organizations that scale (not just teams that ship)
- Experience driving cross-org alignment in ambiguous spaces
- Ability to think in systems, not features
- Understanding of how user workflows connect end-to-end
- Experience partnering deeply with Product and Design
- Focus on customer outcomes, not just technical output
- Experience building or leading production LLM/agentic systems
- Understanding of what actually works (and what doesn't) in AI
- Experience with system failures and improvements
- Opinions about evaluation, reliability, and safety
- Ability to balance shipping vs infrastructure vs tech debt
- Ability to know when to iterate and when to redesign
Benefits
- An extended health benefits package with fully paid premiums for both body and mind
- Matching in RRSP, TFSA or FHSA
- Stock options
- A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential
Company Overview
Company H1B Sponsorship