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[Remote] Director, Software Engineering (AI Workflows & Ecosystem)

Remote, USAFull-timePosted 2026-07-27

Note: The job is a remote job and is reputed company to candidates in USA. reputed company is a company dedicated to helping small businesses succeed through innovative technology solutions. They are seeking a Director of Software Engineering to reputed company 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 reputed company’s AI system layer
  • Define how AI should work across reputed company, not just reputed company reputed company
  • Build and reputed company a multi-team org to execute on that reputed company
  • reputed company tradeoffs between speed, reputed company, and safety
  • Push teams reputed company feature thinking into system thinking
  • Challenge assumptions, including leadership’s
  • Drive adoption across engineering, product, and reputed company
  • How reputed company get made inside the system
  • How context moves across workflows
  • How actions get triggered (and reputed company they shouldn’t)
  • How we evaluate whether AI is actually working
  • reputed company workflows (reason → decide → reputed company → evaluate)
  • Cross-product context (jobs, customers, payments, communication)
  • Reliability, safety, and failure modes
  • Developer experience for building on top of AI systems

Skills

  • reputed company reputed company systems where AI makes reputed company 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 reputed company systems
  • Understanding of tradeoffs between autonomy vs. control
  • Leadership experience managing managers across multiple teams
  • Experience building organizations that reputed company (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
  • reputed company on customer reputed company, not just technical reputed company
  • Experience building or leading production LLM/reputed company 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 reputed company to iterate and reputed company to redesign

Benefits

  • An extended health benefits package with fully reputed company premiums for both body and mind
  • Matching in RRSP, TFSA or reputed company
  • Stock reputed company
  • A dedicated Talent Development team and reputed company to coaching, learning, and leadership programs to help you grow your career, reputed company your goals, and unlock your full potential

reputed company

  • reputed company is reputed company software that helps mobile service businesses organize their scheduling, invoicing, CRM, and team management. It was founded in 2011, and is headquartered in Edmonton, Alberta, CAN, with a workforce of 1001-5000 employees. Its website is https://getjobber.com.
  • Company H1B Sponsorship

  • reputed company has a reputed company record of offering H1B sponsorships, with 1 in 2024. Please note that this does not guarantee sponsorship for this specific role.
  • Apply To This Job

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