Director, Software Engineering (AI Workflows & Ecosystem)

About This Opportunity

Our talent team is representing a confidential SaaS organization in Canada that's transforming how service-based businesses operate. They've already deployed AI capabilities in production—voice systems, automated responses, embedded intelligence—but those capabilities exist as isolated features rather than as a unified, intelligent platform.

This Director role exists to change that. You'll own the evolution from fragmented AI features to cohesive, proactive workflows that anticipate what business owners need before they ask.

The end users aren't asking for "AI." They're overwhelmed operators—plumbers finishing jobs at 6 PM, cleaners managing dozens of clients—who need systems that remove decisions, not add complexity.

Responsibilities

• Own the end-to-end AI system layer across the entire product, not a single team or feature set
• Lead approximately 30 engineers across 4–6 teams, managing 4–6 engineering managers and senior engineering managers
• Define how intelligence flows across the platform: AI foundations, copilot layer, automation execution, marketplace/integrations, and emerging surfaces
• Architect how decisions get made, how context moves across workflows, how actions trigger, and how the system evaluates its own effectiveness
• Build agentic workflows that reason, decide, act, and evaluate across jobs, customers, payments, and communication contexts
• Establish reliability, safety, observability, and failure-handling standards for production AI systems
• Create shared AI primitives so teams build on common infrastructure rather than reinventing solutions
• Drive cross-organizational alignment with Product, Design, and Data partners in highly ambiguous problem spaces
• Balance tradeoffs between speed, quality, autonomy, and control as the system matures

What We're Looking For

AI Systems Expertise (Non-Negotiable)

• You've built or led production LLM and agentic systems where AI makes decisions and takes actions, not just responds to prompts
• Deep hands-on understanding of agent orchestration, tool use, workflow execution, evaluation (offline and online), and guardrails
• You've managed real-world failure modes and improved system reliability and safety in live environments
• You hold strong, informed opinions on what actually works versus what's AI theatre

Leadership at Scale

• Experience leading manager-of-managers organizations across multiple teams through complexity, not just growth
• Track record building scalable organizations, driving cross-functional alignment, and influencing without authority
• Comfortable challenging assumptions at all levels, including with executive leadership

Product and Systems Thinking

• You think in complete user workflows and end-to-end systems, not isolated features
• Deep partnership experience with Product and Design, grounded in customer outcomes rather than technical output alone
• Ability to reason at the system level about how intelligence should behave across a platform

Execution

• You've balanced shipping velocity against infrastructure investment and technical debt
• Strong judgment about when to iterate versus when to redesign foundational components
• Ability to move fast in ambiguous spaces without creating fragility

How We Work With You

Get A Job.ai represents this client exclusively for this search. When you apply through our platform, one of our recruiters will conduct an initial screening to understand your background and ensure alignment with the role requirements. If there's a strong match, we'll submit your profile to our client and coordinate all interview stages on your behalf.

Please apply only through Get A Job.ai. Direct outreach to the client may disqualify your candidacy, as they've engaged us to manage this process end-to-end.

Pay

Pay via Get A Job.ai: $221,800–$300,100 CAD annually. The client designs compensation to reflect skills, experience, and role complexity, with fully established hires typically starting around the midpoint. The range supports progression from onboarding through deep expertise and lasting impact.

The total package includes extended health benefits with fully paid premiums, retirement matching, and stock options.

Equal Opportunity

Get A Job.ai is committed to inclusive hiring practices. We welcome applicants of all backgrounds and will provide accommodation at any stage of the process upon request.