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About the Role

This role focuses on preparing Westland’s workforce for AI, emerging technologies, and new ways of working, supporting the Future Ready Workforce strategy by leading learning and capability-building initiatives.

Responsibilities

Lead the People & Performance components of Westland’s Future Ready Workforce roadmap and manage program plans, including scope, objectives, deliverables, milestones, resources, risks, dependencies, budgets, governance, and executive reporting.
Partner across People & Performance, Organizational Change Management, Technology, Business Technology Enablement and business teams, to translate transformation priorities into workforce readiness, future skills, capability, role, workflow, and learning requirements.
Coordinate capability mapping, skill-gap analysis, and future capability planning while supporting recommendations related to workforce planning, role design, talent mobility, career pathways, reskilling, and future talent pipelines.
Build and lead Westland’s cross-functional AI Champion Network, establishing its operating model, expectations, priorities, measures, and cadence while creating opportunities to share proven use cases, challenges, emerging practices, and reusable resources.
Partner with Learning & Development and external vendors to develop role-based learning pathways and practical resources such as playbooks, use-case libraries, prompt frameworks, guides, workshops, facilitated practice, office hours, and communities of practice.
Help employees and leaders use AI-enabled ways of working effectively and responsibly, including developing the judgment to evaluate AI-generated work for accuracy, quality, usefulness, completeness, risk, and appropriate human review.
Partner with Organizational Change Management, Communications, the Business Technology Enablement Office, and business leaders to support successful adoption and address barriers related to capability, confidence, behaviours, process friction, expectations, and leader support.
Establish and track measures of program delivery, workforce readiness, capability, adoption, workflow application, and business impact, providing concise executive reporting and using feedback and insights to continuously improve enablement strategies and programs.

Requirements

5+ years of experience leading complex learning programs, organizational effectiveness, learning and capability, change enablement, workforce planning, or related initiatives.
Demonstrated experience leading cross-functional initiatives in a complex, and evolving organization, with the ability to build trusted relationships and influence without direct authority.
Ability to translate business strategy and emerging technology trends into practical capability, learning, and adoption plans.
Working knowledge of AI-enabled ways of working, digital adoption, responsible use, and the organizational conditions required to support successful adoption.
Strong program and project management skills, including integrated planning, governance, risk and dependency management, budget oversight, vendor management, and executive reporting.
Analytical problem solver who can define meaningful measures and use data, feedback, and insights to evaluate progress and guide decisions.
Excellent communicator, facilitator, and presenter who can make complex concepts clear, practical, and relevant to a variety of audiences.
Experience with champion networks, communities of practice, insurance, financial services, retail or distributed organizations.

Skills

AI Enablement
Workforce Readiness
Learning Programs
Organizational Effectiveness
Capability Building
Change Enablement
Workforce Planning
Cross-functional Leadership
Relationship Building
Influence
Business Strategy Translation
Emerging Technology Translation
AI-enabled Ways of Working
Digital Adoption
Responsible AI Use
Program Management
Project Management
Integrated Planning
Governance
Risk Management
Dependency Management
Budget Oversight
Vendor Management
Executive Reporting
Analytical Problem Solving
Data Analysis
Communication
Facilitation
Presentation Skills
Champion Networks
Communities of Practice

Location

Greater Vancouver Area
Greater Toronto Area

Work Type

Hybrid
24-month contract

Experience Level

5+ years of experience

Education Level

Degree or equivalent experience in a related field
Certifications in program/project management, change management, adult learning or workforce planning are considered assets

Salary/Compensations

$96,000 to $120,000 based on a 35-hour work week

Benefits

Financial assistance for approved work-related training/development courses leading to certification
Programs that offer professional development, including seminars and conferences
An open, flexible and welcoming workplace
Plenty of opportunities to grow and learn
Autonomy to own your own success
Inclusive culture
Flexible paid Values Days to celebrate days important to you
Paid Volunteer Days for employees as part of Amplifying Communities

About the Company

Westland is committed to continuous learning where employees can grow their potential and write the stories of their careers.
The Westland story is all about growth, and that means plenty of possibility for everyone on our team.
Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment.
We strive to be much more than a great place to work. Here, you join a collective of incredibly vibrant, purpose driven, and open-minded people.
Westland Insurance Ltd. is an inclusive organization that values diversity in its workforce.
Westland Insurance Ltd. encourages applications from all qualified individuals and will accommodate applicants' disability-related needs, up to the point of undue hardship, throughout all stages of the recruitment and selection process.

Equal Opportunity

We listen, champion equity and diversity, and create safe welcoming spaces where everyone has a voice and is free to be themselves.
Westland Insurance Ltd. encourages applications from all qualified individuals and will accommodate applicants' disability-related needs, up to the point of undue hardship, throughout all stages of the recruitment and selection process.
If you require a disability-related accommodation in order to participate in the recruitment process, please contact the recruitment team by email at careers@westlandinsurance.ca