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Cutover Lead

Insight Global

Chicago, IL, United States Full-time June 16, 2026
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Vacancy Description

Job Description
Own and execute the end-to-end cutover strategy across two major go-lives
Act as the single point of accountability (“double-click owner”) for deployment coordination
Build and manage detailed cutover plans, timelines, dependencies, and critical paths
Coordinate cutover activities across:

Workday (FDM changes, Ref ID updates)
OneStream Planning (Oct 2026 go-live)
OneStream Consolidations & Reporting (Jan 2027 go-live)
Boundary systems and integrations

Lead cutover rehearsals and mock go-lives
Ensure data readiness, including final loads, reconciliations, and validation
Manage cross-system dependencies and downstream impacts
Drive business readiness (UAT sign-offs, training completion, operational readiness)
Define and manage go / no-go decision criteria
Lead hypercare planning and execution post go-live
Own risk, issue, and mitigation tracking for cutover activities
Coordinate communication across technical and...

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