D365 Rollout Cutover Manager

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

• 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

Data Migration & System Readiness

• 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

Risk, Issue & Dependency Management

• 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

Stakeholder Communication & Governance

• 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

Training & Transition Support

• Coordinate end-user readiness, including training alignment and support planning
• Support hypercare and post-go-live stabilization to ensure successful adoption and operational continuity

Key Skills & Experience

Experience

• 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

Technical & Functional Expertise

• 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

Project & Delivery Skills

• 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

Soft Skills

• 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

Good-to-Have Skills

• 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

Work Environment

• Location: Greater Toronto Area (Hybrid - minimum 3 days onsite)
• Travel: 25%-50% travel across Canada, U.S., and LATAM