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Program Manager, AI Enablement & Workforce Readiness

Westland Insurance Group
Toronto, CAN
Full-time
Hybrid
$96,000 to $120,000
Discovered 2 weeks ago
AI-enabled ways of workingWorkforce readinessLearning and capability developmentProgram and project managementChange enablementWorkforce planning

Full Job Posting

Role overview

A 24-month contract focused on preparing Westland’s workforce for AI, emerging technologies, and new ways of working.

Supports the Future Ready Workforce strategy through learning and capability-building initiatives.

This is not a technical AI role; the work translates technology and business transformation into practical workforce capabilities.

Hybrid role open to candidates in the Greater Vancouver or Greater Toronto Area, with work from home and regular time in a local office.

Compensation

  • Expected hiring range is $96,000 to $120,000 based on a 35-hour work week; actual salary depends on qualifications, experience, market conditions, and internal equity.

Qualifications

  • 5+ years leading complex learning, organizational effectiveness, capability, change enablement, workforce planning, or related initiatives.
  • Experience leading cross-functional initiatives in complex, evolving organizations and influencing without direct authority.
  • Ability to translate business strategy and emerging technology into capability, learning, and adoption plans.
  • Working knowledge of AI-enabled work, digital adoption, responsible use, and organizational adoption conditions.
  • Strong program and project management, analytical problem-solving, communication, facilitation, and presentation skills.
  • Experience with champion networks, communities of practice, insurance, financial services, retail, or distributed organizations is valued.
  • A related degree or equivalent experience is sought; relevant program/project management, change, adult learning, or workforce planning certifications are assets.

Responsibilities

  • Lead the People & Performance components of the Future Ready Workforce roadmap and oversee plans, scope, deliverables, resources, risks, budgets, governance, and executive reporting.
  • Translate transformation priorities into workforce readiness, future skills, capability, role, workflow, and learning requirements with cross-functional partners.
  • Coordinate capability mapping, skill-gap analysis, and future capability planning; support workforce planning, role design, talent mobility, career pathways, reskilling, and talent pipelines.
  • Build and lead the AI Champion Network, establishing its operating model, expectations, priorities, measures, and cadence.
  • Develop role-based learning pathways and practical resources with Learning & Development and external vendors.
  • Help employees and leaders use AI responsibly and evaluate AI-generated work with appropriate human review.
  • Support adoption and address capability, confidence, behavior, process, expectation, and leadership barriers.
  • Track program delivery, workforce readiness, capability, adoption, workflow application, and business impact; use feedback to improve programs.

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