Job Title

Role SummaryThe 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 ResponsibilitiesCutover Planning & ExecutionLead the Cutover workstream for Microsoft Dynamics 365 implementations, ensuring all activities are delivered on time and as plannedDevelop detailed cutover strategies, execution plans, runbooks, and readiness checklistsCoordinate mock cutovers, dress rehearsals, and final production cutoversData Migration & System ReadinessOversee data migration activities, ensuring data completeness, accuracy, and reconciliation between legacy and target systemsCoordinate system validation, integration testing, and User Acceptance Testing (UAT) to confirm production readinessEnsure all entry and exit criteria for cutover milestones are achievedRisk, Issue & Dependency ManagementIdentify, assess, and mitigate risks related to cutover, data, environment readiness, and business continuityManage inter-stream dependencies and proactively resolve issues impacting timelinesSupport go/no-go decision-making with clear risk assessments and mitigation strategiesStakeholder Communication & GovernanceAct as the primary point of contact for all cutover-related activities across business and technology teamsProvide regular status updates, dashboards, and executive-level reportingFacilitate cross-functional meetings and lead command center activities during deploymentTraining & Transition SupportCoordinate end-user readiness, including training alignment and support planningSupport hypercare and post-go-live stabilization to ensure successful adoption and operational continuity Key Skills & ExperienceExperienceProven experience leading cutover activities for Microsoft Dynamics 365 implementationsExperience with large-scale or global ERP/CRM rolloutsStrong background in complex system transformations with multiple data sourcesExperience working in fast-paced, matrixed program environmentsTechnical & Functional ExpertiseStrong understanding of Microsoft Dynamics 365 modules and deployment methodologiesHands-on experience with cutover processes, including:Data migrationEnvironment managementSystem validationTesting cyclesFamiliarity with integrations between Dynamics 365 and upstream/downstream systemsProject & Delivery SkillsStrong project management skills with the ability to build and execute detailed cutover plansExcellent analytical and problem-solving abilities under tight timelinesAbility to manage multiple priorities with strong attention to detailSoft SkillsExcellent communication and presentation skills across technical and business audiencesProven ability to lead cross-functional teams and influence without direct authorityStrong decision-making capability during high-pressure cutover windowsCollaborative, proactive, and team-oriented mindset Good-to-Have SkillsExperience with global or multi-country Dynamics 365 rolloutsKnowledge of data migration tools, ETL processes, and reconciliation techniquesExperience with Agile, SAFe, or hybrid delivery modelsFamiliarity with Azure environments, DevOps, and release managementExperience in ERP/CRM transformations within the hospitality industry (e.g., hotels)Relevant certifications such as PMP, SAFe, or Prosci Work EnvironmentLocation: Greater Toronto Area (Hybrid minimum 3 days onsite)Travel: 25%50% travel across Canada, U.S., and LATAM