Agile Program Manager (Technical) - AI-Enabled DeliveryWork Arrangement: We are seeking an experienced Technical Agile Program Manager to lead complex, cross-functional technology programs across Azure cloud and on-premise environments. The ideal candidate will combine strong program management fundamentals, hands‑on knowledge of Agile delivery practices, and practical experience leveraging AI tools to improve program execution, reporting, risk management, and operational efficiency. This role goes beyond traditional program management.

The successful candidate will identify and implement AI‑enabled workflows that reduce manual effort, improve delivery visibility, strengthen governance, and make program management practices more efficient, consistent, and scalable. The candidate will collaborate with engineering, product management, business, finance, risk, and compliance stakeholders to deliver technology initiatives in a structured, transparent, and controlled environment. Own end‑to‑end technical program management, including intake, planning, execution, delivery, and closure across Azure and on‑premise environments.

Lead Agile delivery across multiple teams using Scrum, Kanban, and Secure methodologies. Coordinate cross‑functional teams to manage priorities, dependencies, milestones, risks, issues, and delivery commitments. Partner with engineering, product, business, finance, risk, and compliance stakeholders to align program objectives and communicate progress, risks, and trade‑offs.

Identify and implement AI‑enabled workflows for automated status reporting, meeting summaries, documentation generation, risk identification, dependency mapping, and program insights. Establish and maintain program governance artifacts, including roadmaps,



RAID logs, dashboards, delivery plans, and executive‑level reports.

Promote

DevOps principles, continuous integration and continuous delivery (CI/CD), and continuous improvement across technical teams. Manage escalations, resolve cross‑team conflicts, and balance technical constraints with business priorities and regulatory requirements. Apply appropriate human oversight, data governance, and judgment when using AI tools in program management workflows.

Contribute to the development of repeatable, scalable practices for AI‑enabled technical program and portfolio management. Proven experience as a Technical Program Manager, Agile Program Manager, Technical Project Manager, or Senior Technical Delivery Manager. Demonstrated success managing multiple concurrent, cross‑functional technology programs with complex dependencies.

Strong applied knowledge of Agile methodologies, including Scrum, Kanban, and SAFe.

Experience with Agile planning, backlog refinement, flow management, delivery governance, and continuous improvement. Hands‑on experience using Jira and Confluence for program management and delivery tracking. Working knowledge of Microsoft Azure and on‑premise infrastructure environments.

Ability to engage in technical discussions involving infrastructure, cloud services, platform migrations, and production operations. Practical experience using generative AI tools or AI‑assisted workflows to improve productivity, reporting, documentation, analysis, or program delivery. Strong experience in stakeholder management, executive communication, risk management, dependency management, and issue resolution.

Ability to translate technical information into clear, actionable updates for business and technology stakeholders.

📌 Head of Technical Programme Management (Winnipeg)
🏢 EnableIT
📍 Winnipeg