D365 Rollout Cutover Manager

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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.

• Lead the Cutover workstream for Microsoft Dynamics 365 implementations, ensuring all activities are delivered on time and as planned

• Develop detailed cutover strategies, execution plans, runbooks, and readiness checklists

• Coordinate mock cutovers, dress rehearsals, and final production cutovers

• Oversee data migration activities, ensuring data completeness, accuracy, and reconciliation between legacy and target systems

• Coordinate system validation, integration testing, and User Acceptance Testing (UAT) to confirm production readiness

• Ensure all entry and exit criteria for cutover milestones are achieved

• Identify, assess, and mitigate risks related to cutover, data, environment readiness, and business continuity

• Manage inter-stream dependencies and proactively resolve issues impacting timelines

• Support go/no-go decision-making with clear risk assessments and mitigation strategies

• Act as the primary point of contact for all cutover-related activities across business and technology teams

• Provide regular status updates, dashboards, and executive-level reporting

• Facilitate cross-functional meetings and lead command center activities during deployment

• Coordinate end-user readiness, including training alignment and support planning

• Support hypercare and post-go-live stabilization to ensure successful adoption and operational continuity

• Proven experience leading cutover activities for Microsoft Dynamics 365 implementations

• Experience with large-scale or global ERP/CRM rollouts

• Strong background in complex system transformations with multiple data sources

• Experience working in fast-paced, matrixed program environments

• Strong understanding of Microsoft Dynamics 365 modules and deployment methodologies

• Hands-on experience with cutover processes, including:

  • Data migration

  • Environment management

  • System validation

  • Testing cycles

• Familiarity with integrations between Dynamics 365 and upstream/downstream systems

• Strong project management skills with the ability to build and execute detailed cutover plans

• Excellent analytical and problem-solving abilities under tight timelines

• Ability to manage multiple priorities with strong attention to detail

• Excellent communication and presentation skills across technical and business audiences

• Proven ability to lead cross-functional teams and influence without direct authority

• Strong decision-making capability during high-pressure cutover windows

• Collaborative, proactive, and team-oriented mindset

• Experience with global or multi-country Dynamics 365 rollouts

• Knowledge of data migration tools, ETL processes, and reconciliation techniques

• Experience with Agile, SAFe, or hybrid delivery models

• Familiarity with Azure environments, DevOps, and release management

• Experience in ERP/CRM transformations within the hospitality industry (e.g., hotels)

• Relevant certifications such as PMP, SAFe, or Prosci

• Location: Greater Toronto Area (Hybrid – minimum 3 days onsite)

• Travel: 25%–50% travel across Canada, U.S., and LATAM