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Added 5 mins ago
BT
Account Executive - Full-Cycle (North America)
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Montreal, QC
- Full-time
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Lead Product Manager
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Canada
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Gestionnaire des services TI / IT Service Manager
mthree
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Added 18 mins ago
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Toronto, ON
- $90,000 to $120,000 CAD / year
- Full-time
…a pivotal stage of growth through expanding our government program footprint, deepening our employer partnerships, and building the team to take us…
Added 20 mins ago
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Toronto, ON · Ottawa, ON · Montreal, QC · Quebec, QC · Vancouver, BC · AB · Surrey, BC · Calgary, AB · Tsuut'ina, AB
- Full-time
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Talent Acquisition Team at Westland Insurance. Text reply only.

Program Manager, AI Enablement & Workforce Readiness

Toronto, ON, Canada
Surrey, BC, Canada

Expected Compensation: The expected hiring range for this role is $96,000 to $120,000 based on a 35-hour work week.

Apply About employer

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Job details

Pay: Expected Compensation: The expected hiring range for this role is $96,000 to $120,000 based on a 35-hour work week.
Posting language: English
Posted: Oct 6, 2026

Original job description

Program Manager, AI Enablement & Workforce Readiness

We’re searching for a Program Manager, AI Enablement & Workforce Readiness. Are you searching for new possibilities?

This is a 24-month contract opportunity focused on preparing Westland’s workforce for AI, emerging technologies, and new ways of working. This is a hybrid role open to candidates based in the Greater Vancouver or Greater Toronto Area. You’ll enjoy the flexibility of working from home while staying connected with your team through regular time in one of our local offices.

Expected Compensation: The expected hiring range for this role is $96,000 to $120,000 based on a 35-hour work week. Actual offered salary will depend on the successful candidate’s qualifications and experience, as well as market conditions for the role and internal equity.

Westland is committed to continuous learning where employees can grow their potential and write the stories of their careers. Financial assistance is available for approved work-related training/development courses leading to certification, and programs that offer professional development, including seminars and conferences.

Discover what’s possible, with Westland

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. As we continue to open new doors, we're inviting amazing people like you to join us.

As a Program Manager, AI Enablement & Workforce Readiness, you’ll help prepare Westland’s workforce for changing business needs, emerging technologies, and new ways of working. You’ll support our Future Ready Workforce strategy by leading learning and capability-building initiatives that help employees and leaders build the skills and confidence to work effectively in an evolving environment.

This isn’t a technical AI role. You don’t need to be Westland’s deepest technical AI expert. In this role you will work closely with our People & Performance, Organizational Change Management, Business Technology Enablement, Technology, and business teams, to translate emerging technology and business transformation into practical, measurable, workforce capabilities.

Interested in learning more?

Why you’ll love Westland:

An open, flexible and welcoming workplace

Plenty of opportunities to grow and learn

Autonomy to own your own success

Be part of our inclusive culture, alongside an extraordinarily talented community of people with a wide variety of backgrounds

Flexible paid Values Days to celebrate days important to you

Paid Volunteer Days for employees as part of Amplifying Communities, a program to support causes that matter most to our employees

Why we’ll love You:

You have 5+ years of experience leading complex learning programs, organizational effectiveness, learning and capability, change enablement, workforce planning, or related initiatives

You have demonstrated experience leading cross-functional initiatives in a complex, and evolving organization, with the ability to build trusted relationships and influence without direct authority

You can translate business strategy and emerging technology trends into practical capability, learning, and adoption plans

You bring a working knowledge of AI-enabled ways of working, digital adoption, responsible use, and the organizational conditions required to support successful adoption

You have strong program and project management skills, including integrated planning, governance, risk and dependency management, budget oversight, vendor management, and executive reporting

You’re an analytical problem solver who can define meaningful measures and use data, feedback, and insights to evaluate progress and guide decisions

You’re an excellent communicator, facilitator, and presenter who can make complex concepts clear, practical, and relevant to a variety of audiences

You have experience with champion networks, communities of practice, insurance, financial services, retail or distributed organizations

A degree or equivalent experience in a related field; along with certifications in program/project management, change management, adult learning or workforce planning are considered assets

Once here, you’ll:

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

Want to get to know each other better? Send your resume our way.

You belong here
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. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment. You will be supported and respected for who you are and for the voice you add to the conversation.

At Westland, you will feel the power of community. Westland Insurance Ltd. is an inclusive organization that values diversity in its workforce. 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

Apply About employer

More about this job

Responsibilities

The Program Manager will lead learning and capability-building initiatives to prepare the workforce for AI and emerging technologies. They will partner with cross-functional teams to translate business transformation into practical workforce readiness and adoption plans.

Requirements

Candidates must have 5+ years of experience in learning programs, organizational effectiveness, or change enablement. Strong project management skills and the ability to influence without direct authority are essential for this role.

Skills

Program management
Change management
Workforce planning
Capability building
Organizational effectiveness
Strategic planning
Cross-functional leadership
Digital adoption
Stakeholder management
Data analysis
Facilitation
Communication
Project management
Budget oversight
Vendor management
Executive reporting

Benefits

Financial assistance for professional development
Flexible paid Values Days
Paid Volunteer Days
Inclusive culture

Visa sponsorship

Not detected in the job text

Keywords

AI Enablement
Workforce Readiness
Program Management
Change Management
Organizational Change Management
Future Ready Workforce
Capability Mapping
Skill-gap Analysis
AI Champion Network
Digital Adoption
Learning & Development
Business Transformation
Project Management
Governance
Risk Management
Budget Oversight
Vendor Management
Executive Reporting
Data Analysis
Facilitation
Insurance
Financial Services
Retail
Prompt Frameworks
Communities of Practice
Reskilling
Career Pathways
Talent Mobility
Role Design
Workflow Application

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