AI Program Lead

FacilityOS•North York, ON

1d•CA$140,000 - CA$155,000•Hybrid

About The Position

The AI Program Lead reports directly to the CTO and serves as the central driver of AI strategy execution across FacilityOS. This is a high-visibility, cross-functional role that sits at the intersection of strategic program management, organizational enablement, and executive governance. The ideal candidate brings both operational discipline and a genuine understanding of AI, someone who can manage a complex portfolio of initiatives, build the foundational infrastructure that makes AI adoption sustainable, and communicate program health clearly to C-suite leadership. Department leaders own the AI transformation of their own functions, including the discovery, tooling, and outcomes of the agents and initiatives within their teams. The Program Lead's role is to consolidate that effort into a single coherent program: holding teams accountable, pushing initiatives forward, and guiding and coaching departments through adoption. The Program Lead is the organization's single voice of truth for enablement progress and success.

Requirements

5+ years of experience in program management, strategic operations, or technology leadership within a SaaS or enterprise technology environment
Demonstrated ability to manage complex, cross-functional programs with multiple workstreams, stakeholders, and competing priorities
Strong working knowledge of AI tools, data platforms, or enterprise SaaS implementations
Experience designing operational frameworks, governance structures, or enablement programs at an organizational level
Excellent communication skills with a track record of presenting to and influencing C-suite and VP-level audiences
Comfortable driving progress in high-ambiguity, fast-moving environments without direct authority

Nice To Haves

Familiarity with AI concepts including LLMs, agent frameworks, knowledge management, and data infrastructure is a strong advantage
PMP, Agile, or equivalent certifications are a plus but not required

Responsibilities

Own end-to-end execution across a portfolio of cross-functional AI initiatives, from evaluation through launch to value realization
Define and maintain program governance structures including owners, milestones, dependencies, and risk registers
Proactively identify blockers, resolve execution gaps, and escalate delays with clarity and context
Drive accountability across teams without direct authority, ensuring high-quality and timely delivery
Design and implement org-wide frameworks and standards that enable consistent, scalable AI adoption across departments
Lead the development of knowledge infrastructure, including content architecture, data foundation layers, and AI-readiness standards that supports enterprise AI deployment
Evaluate and guide the adoption of data platforms and tooling in support of the company's AI strategy
Establish and maintain consistent execution tools, tracking practices, and reporting standards across teams
Facilitate weekly AI Council alignment meetings with VP and C-suite stakeholders, including the CTO, CRO, CFO, and CEO, a forum for visibility and cross-functional alignment; formal approvals remain with C-level leadership
Prepare and deliver clear, high-quality executive status updates covering portfolio health, risks, and items requiring C-level decision or approval
Lead technical coordination forums (e.g., AI Tech/Integration SWAT) bridging engineering, product, and operations
Maintain centralized program visibility into project status, risks, resource needs, and strategic alignment
Ensure program initiatives are evaluated against corporate compliance and security policy requirements, escalating for review and approval as needed
Partner with VPs and functional leads across all departments to align goals, scope, and delivery timelines
Manage cross-functional handoffs and interdependencies to minimize execution friction
Coordinate external vendor and contractor engagements, ensuring accountability and alignment to project outcomes
Serve as the connective layer between CTO strategic priorities and department-level execution
Guide and coach department leaders as they own the AI transformation and use of AI within their own functions