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Program Manager, AI Enablement & Workforce Readiness

Westland Insurance Group Ltd.
CAN
Full-time
Mid-Senior
Hybrid
CAD 96,000 to CAD 120,000
Discovered 2 weeks ago
Learning program leadershipOrganizational change managementWorkforce planning and capability buildingProgram and project managementAI-enabled ways of workingDigital adoption

Full Job Posting

Role overview

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

The role leads learning and capability-building initiatives as part of the Future Ready Workforce strategy; it is not a technical AI role.

The position is hybrid, with work from home and regular time in a local office, and is open to candidates in the Greater Vancouver or Greater Toronto Area.

Compensation

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

Qualifications

  • At least five years of experience leading complex learning, organizational effectiveness, capability, change enablement, workforce planning, or related initiatives.
  • Experience leading cross-functional work in a complex, evolving organization and influencing without direct authority.
  • Ability to translate business strategy and emerging technology into practical capability, learning, and adoption plans.
  • Working knowledge of AI-enabled work, digital adoption, responsible use, and conditions supporting successful adoption.
  • Strong program and project management, including planning, governance, risks, dependencies, budgets, vendors, and executive reporting.
  • Analytical problem-solving skills, meaningful measurement, and use of data, feedback, and insights.
  • Excellent communication, facilitation, and presentation skills for varied audiences.
  • Experience with champion networks, communities of practice, insurance, financial services, retail, or distributed organizations is an asset.
  • A degree or equivalent experience in a related field; certifications in program/project management, change management, adult learning, or workforce planning are assets.

Responsibilities

  • Lead People & Performance components of the workforce roadmap and manage program scope, objectives, deliverables, milestones, resources, risks, dependencies, 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, mobility, career pathways, reskilling, and talent pipelines.
  • Build and lead the AI Champion Network, defining 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 for quality, usefulness, completeness, risk, and need for human review.
  • Support successful adoption and address barriers related to capability, confidence, behaviours, processes, expectations, and leadership.
  • Measure program delivery, readiness, capability, adoption, workflow application, and business impact; report results and improve enablement.

Benefits and workplace

  • The employer describes an open, flexible, and welcoming workplace, development opportunities, paid Values Days, paid Volunteer Days, and assistance for approved work-related training and development.

Recruitment AI disclosure

  • Recruitment AI is used only to transcribe candidate-call notes with consent and is not used to screen, evaluate, or select candidates.

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