We’re searching for a Program Manager, AI Enablement & Workforce Readiness. This is a 24-month contract opportunity focused on preparing Westland’s workforce for AI, emerging technologies, and new ways of working. You’ll enjoy the flexibility of working from home while staying connected with your team through regular time in one of our local offices.

Actual offered salary will depend on the successful candidate’s qualifications and experience, as well as market conditions for the role and internal equity. Financial assistance is available for approved work-related training/development courses leading to certification, and programs that offer professional development, including seminars and conferences. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment.

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. An open, flexible and welcoming workplace 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 significant to you Paid Volunteer Days for employees as part of Amplifying Communities, a program to support causes that matter most to our employees You have 5+ years of experience leading complex learning programs, organizational effectiveness, learning and capability, change enablement,



workforce planning, or related initiatives 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 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 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 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. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment. 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. 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

📌 Program Manager, Ai Enablement & Workforce Readiness (Winnipeg)
🏢 Westland Insurance Group
📍 Winnipeg