Program Manager, AI Enablement & Workforce Readiness

Westland Insurance Group Ltd.; Toronto; Hybrid; CAD 96,000 - 120,000; Full time

Benefits offered by this job

Flexible Values Days

Volunteer Days

Training support

Job summary

Westland Insurance Group Ltd. is seeking a Program Manager, AI Enablement & Workforce Readiness for a 24-month contract. Hybrid role preferred in the Greater Vancouver or Greater Toronto Area with home office flexibility and regular in-person collaboration.

The role focuses on leading learning and capability-building initiatives to prepare Westland’s workforce for AI and evolving technology, translating strategy into practical readiness programs and measurable outcomes.

Qualifications

• 5+ years of experience leading complex learning programs and workforce readiness.
• Ability to influence without direct authority in a cross-functional setting.
• Translate business strategy into learning and capability plans.
• Knowledge of AI-enabled ways of working and responsible use.
• Strong program and project management, governance, and executive reporting.
• Excellent communication, facilitation, and presentation skills.
• Experience in insurance/financial services or distributed organizations.
• Degree or equivalent; certifications in program/project management or change management are assets.

Responsibilities

• Lead People & Performance components of the Future Ready Workforce roadmap with program plans and governance.
• Coordinate capability mapping, skill-gap analysis, and future capability planning.
• Build and lead AI Champion Network and cross-functional collaboration.
• Develop role-based learning pathways and practical resources with vendors.
• Ensure responsible AI adoption and measure program impact with executive reporting.
• Address barriers to capability, confidence, and leadership support.

Skills

Program management

Cross-functional leadership

Stakeholder engagement

Analytics & measurement

Communication skills

Education

Bachelor's degree or equivalent

Job description

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.

Reason for Vacancy:

This is a newly created role to support our expanding operations.

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.

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

AI statement:

As part of our commitment to transparency, we want to let you know that while our recruitment system includes AI capabilities, these are never used to screen, evaluate, or select candidates. The only AI functionality that Westland uses is for transcribing notes during candidate calls, and this occurs with your consent. These tools aren’t used to make any hiring decisions throughout our recruitment process.

We 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 [e-mail].