Director, Technology Workforce Transformation and Future of Work

Director, Technology Workforce Transformation and Future of Work

Requisition ID: 259852

Join a purpose driven winning team, committed to results, in an inclusive and high‑performing culture.

The Director, Workforce Transformation & Future of Work is a senior leader responsible for reimagining how work gets done across the enterprise—with Technology as a primary transformation engine. This role designs and delivers multi‑year workforce, skills, and operating model strategies to ensure the organization has the future‑ready capabilities, talent, and ways of working required to deliver on enterprise priorities including technology modernization, AI adoption, automation, and digital transformation.

Operating as a strategic anchor for workforce transformation, the Director partners closely with the CIO organization, senior Technology leaders, HR Business Partners, Talent COEs, Finance, and enterprise stakeholders to redesign work, roles, and workforce models—translating strategy into measurable, scalable impact. The role blends enterprise‑level strategy, analytics, and hands‑on execution, moving beyond advisory to deliver real transformation.

What You’ll Do:

• Enterprise & Technology Workforce Strategy: develop and deliver a multi‑year workforce transformation and future‑of‑work strategy aligned to enterprise and Technology priorities.
• Redesign how work is done by integrating people, skills, technology, AI, and operating models.
• Conduct workforce foresight, scenario planning, and skills supply/demand modelling across critical domains (engineering, cloud, cybersecurity, data, AI, automation).
• Provide strategic guidance to senior leaders on skills risk, labor market trends, organizational design, and workforce investment decisions.
• Lead future‑state work and operating model design, including role definition, team structures, decision rights, and workflows.
• Apply AI‑enabled organization design and workforce analytics to assess current states, model scenarios, and generate insights.
• Partner with Technology and business leaders to reimagine value delivery across platforms and functions.
• Translate designs into scalable, repeatable models embedded into enterprise execution.
• Skills Strategy & Capability Modernization: define and operationalize an enterprise skills strategy with deep Technology integration; build skills frameworks, role architecture, and capability roadmaps for critical future roles (AI/ML, cloud engineering, cyber, DevOps, SRE).
• Lead large‑scale upskilling and reskilling initiatives in partnership with HR, Learning, Academia, and external providers; advance adoption of a skills‑based organization, embedding skills into workforce planning, talent, and development decisions.
• Design and expand early‑career and alternative talent pathways (internships, co‑ops, apprenticeships, returnships); build partnerships with universities, bootcamps, and technology skilling organizations; enable career pathways, mobility, and internal talent marketplaces to drive engagement and retention.
• Pilot and scale innovative workforce models, building playbooks for enterprise adoption.
• Organizational Health, Culture & Ways of Working: lead initiatives to strengthen organizational health, engagement, leadership capability, culture across Technology and adjacent functions; champion modern ways of working, including hybrid work, agile leadership, collaboration, and productivity.
• Integrate organization design, talent, and change management into transformation roadmaps.
• Transformation Execution & Program Leadership: establish KPIs and executive dashboards to track impact on productivity, skills readiness, engagement, and cost; manage budgets, vendors, and cross‑functional delivery teams.
• Stakeholder Partnership & Leadership: act as a trusted partner to Technology executives, HR leaders, and enterprise stakeholders; influence across matrixed, global environments; lead and develop a high‑performing, innovation‑oriented team; represent workforce transformation initiatives in enterprise governance and leadership forums.

What You’ll Bring:

• 10+ years in workforce strategy, organizational design, technology transformation, HR strategy, or related fields.
• Proven experience leading large‑scale workforce or capability transformations in complex, global organizations.
• Strong understanding of technology roles, engineering practices, and future skills trends (AI, cloud, cyber, automation).
• Demonstrated ability to move seamlessly from strategy to execution.
• Strong executive‑level influencing, analytical, and storytelling capabilities.
• Education in business, organizational development, technology, AI, or a related discipline (or equivalent experience).

Working Conditions

• Work in standard office‑based environments located in Scarborough and Downtown Toronto; non‑standard hours are a common occurrence. No external travel required. Ability to come to office 3 times a week.

What's in it for you?

• Join a team focused on building cloud platforms as products, enabling delivery teams across the enterprise.
• Diversity, Equity, Inclusion & Allyship: inclusive culture where every employee is empowered to reach their fullest potential and respected for who they are.
• Accessibility and Workplace Accommodations: commitment to a diverse and inclusive environment while meeting accessibility requirements.
• Upskilling through online courses, cross‑functional development opportunities, and tuition assistance.
• Competitive Rewards program including bonus, flexible vacation, personal, sick days, and benefits starting on day one.
• Community Engagement: opportunities for community engagement and belonging with various programs.

Location: Canada : Ontario : Toronto

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