D365 Cutover Rollout Manager
Role Summary
The D365 Cutover Rollout Manager is responsible for leading and executing end-to-end cutover activities associated with the transition from legacy systems to Microsoft Dynamics 365. This role ensures a controlled, low-risk deployment with minimal disruption to business operations.
The Cutover Manager will design and execute comprehensive cutover strategies, coordinate cross-functional teams, manage interdependencies across applications, oversee data migration and system readiness, and act as the central point of accountability during the cutover phase for large-scale and/or global implementations.
Key Responsibilities
Cutover Planning & Execution
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Lead the Cutover workstream for Microsoft Dynamics 365 implementations, ensuring all activities are delivered on time and as planned
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Develop detailed cutover strategies, execution plans, runbooks, and readiness checklists
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Coordinate mock cutovers, dress rehearsals, and final production cutovers
Data Migration & System Readiness
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Oversee data migration activities, ensuring data completeness, accuracy, and reconciliation between legacy and target systems
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Coordinate system validation, integration testing, and User Acceptance Testing (UAT) to confirm production readiness
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Ensure all entry and exit criteria for cutover milestones are achieved
Risk, Issue & Dependency Management
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Identify, assess, and mitigate risks related to cutover, data, environment readiness, and business continuity
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Manage inter-stream dependencies and proactively resolve issues impacting timelines
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Support go/no-go decision-making with clear risk assessments and mitigation strategies
Stakeholder Communication & Governance
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Act as the primary point of contact for all cutover-related activities across business and technology teams
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Provide regular status updates, dashboards, and executive-level reporting
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Facilitate cross-functional meetings and lead command center activities during deployment
Training & Transition Support
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Coordinate end-user readiness, including training alignment and support planning
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Support hypercare and post-go-live stabilization to ensure successful adoption and operational continuity
Key Skills & Experience
Experience
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Proven experience leading cutover activities for Microsoft Dynamics 365 implementations
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Experience with large-scale or global ERP/CRM rollouts
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Strong background in complex system transformations with multiple data sources
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Experience working in fast-paced, matrixed program environments
Technical & Functional Expertise
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Strong understanding of Microsoft Dynamics 365 modules and deployment methodologies
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Hands-on experience with cutover processes, including:
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Data migration
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Environment management
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System validation
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Testing cycles
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Familiarity with integrations between Dynamics 365 and upstream/downstream systems
Project & Delivery Skills
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Strong project management skills with the ability to build and execute detailed cutover plans
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Excellent analytical and problem-solving abilities under tight timelines
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Ability to manage multiple priorities with strong attention to detail
Soft Skills
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Excellent communication and presentation skills across technical and business audiences
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Proven ability to lead cross-functional teams and influence without direct authority
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Strong decision-making capability during high-pressure cutover windows
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Collaborative, proactive, and team-oriented mindset
Good-to-Have Skills
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Experience with global or multi-country Dynamics 365 rollouts
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Knowledge of data migration tools, ETL processes, and reconciliation techniques
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Experience with Agile, SAFe, or hybrid delivery models
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Familiarity with Azure environments, DevOps, and release management
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Experience in ERP/CRM transformations within the hospitality industry (e.g., hotels)
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Relevant certifications such as PMP, SAFe, or Prosci
Work Environment
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Location: Greater Toronto Area (Hybrid - minimum 3 days onsite)
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Travel: 25%-50% travel across Canada, U.S., and LATAM