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Sr. Cutover Lead to plan and execute transition from legacy systems to Workday

Job in Ottawa, Ontario, Canada
Listing for: S.i. Systems
Contract position
Listed on 2026-06-18
Job specializations:
  • IT/Tech
    IT Project Manager, IT Business Analyst, Systems Analyst, IT Consultant
Job Description & How to Apply Below
Position: Sr. Cutover Lead to plan and execute the transition from legacy systems to Workday

Our public sector client is seeking a Sr. Cutover Lead to plan and execute the transition from legacy systems to Workday

Join a critical ERP transformation project supporting transition to Workday across a national organization. This role designs and leads the end-to-end cutover strategy covering technical deployment, business process readiness, and organizational change management ahead of a fixed November 2 go-live. The position is high-impact, engaging multiple teams to ensure day-one operational readiness across IT, business, and change functions. Candidates will have visibility across leadership and full ownership from planning through execution.

Contract, Remote or Hybrid (Ottawa time zone)

Must Haves

  • Eligible for Reliability Level security clearance
  • Extensive experience in cutover planning and execution for enterprise system or SaaS implementations
  • Proven success leading multi-system migrations with high interdependency and phased go-live
  • Strong technical and business understanding of system integrations
    , identity/access provisioning
    , and release management
  • Experience with Workday or comparable platforms (e.g., SAP, Oracle Cloud)

    • Nice to Have

  • Experience coordinating across IT, OCM, and business functional teams
  • Familiarity with large government or public sector transformation programs
  • Ability to synthesize technical details into business-level decision frameworks

    • Responsibilities

  • Develop and manage the end-to-end cutover strategy and plan
  • Define detailed cutover runbooks, sequencing, timelines, and dependencies
  • Establish go/no-go criteria, readiness checkpoints, and contingency plans
  • Coordinate activities across IT, business leads, SMEs, OCM, and external vendors
  • Ensure alignment between technical and business readiness for Day 1 operations in Workday
  • Lead structured planning workshops and stakeholder working sessions
  • Identify, track, and mitigate risks affecting readiness and execution
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