Deployment & Cutover Lead (x 2 Positions)

Deployment & Cutover Lead (Hybrid) Primary Location: Toronto, Ontario V-Soft Consulting is currently hiring for a Deployment & Cutover Lead for our premier client in Toronto, Ontario. WHAT YOU’LL NEED: Technical Requirements and Certifications » Professional certifications (PMP, PRINCE2, or equivalent). Education and Experience » 10+ years of program/project management experience, with at least 5+ years dedicated to deployment and cutover leadership in large-scale ERP or enterprise transformation programs. Proven track record leading complex ERP greenfield implementations, preferably in retail or consumer-focused industries. Expertise in cutover management, deployment planning, and execution across multiple business functions and geographies. Strong knowledge of data migration strategies, validation processes, and environment readiness. Experience leading large cross-functional teams (100+ people) through cutover and deployment waves. Advanced proficiency with project management tools such as Microsoft Project, including critical path and dependency management. Exceptional communication, facilitation, and ability to present in front of C-level stakeholders. Strong RAID management and contingency planning skills. Ability to operate under aggressive timelines with precision and discipline. Preferred: Experience with ERP solutions such as SAP, Oracle, Microsoft Dynamics. Experience rolling out solutions from BY, Manhattan WMS, GK POS, Adobe or similar enterprise platforms. Exposure to Supply Chain, Merchandising, Finance, POS, and Warehouse Management systems within retail environments. Familiarity with change management and business readiness planning in transformation programs. Strong presentation and communications skills. WHAT YOU’LL DO: Job Responsibilities: Deployment & Cutover Planning: Work closely with our transformation partner’s deployment team and develop, own, and maintain a comprehensive deployment and cutover plan covering dress rehearsals, cutover simulations, mock conversions, data loads, environment readiness, business validation, and final cutover execution. Orchestration & Leadership: Coordinate and align multiple stakeholders (Business, IT, Data, Infrastructure, and Vendors) to ensure all activities are sequenced, dependencies are managed, and cutover milestones are met. Work closely with the Release Leads and Program Leadership to ensure the right level of resourcing is allocated towards deployment and cutover activities. Dress Rehearsals & Mock Runs: Lead multiple end-to-end dress rehearsals, cutover plan read outs and cutover simulations to validate timing, accuracy, and readiness of cutover activities, identifying and resolving issues proactively. Data Loads & Validation: Oversee migration and validation of master data, transactional data, and configuration loads. Ensure business teams are engaged in signoffs and quality assurance. Risk & Contingency Management: Define and track deployment and cutover RAID items. Develop risk and issue responses, contingency plans, and fallback strategies to safeguard business continuity. Go/No-Go Governance: Lead structured Go/No-Go processes with business and IT leadership, ensuring all readiness checkpoints are achieved prior to cutover. Hypercare Management, BCP, DR and Transition to Sustainment: Oversee hypercare and transition planning, ensuring smooth handover from program to operations/sustainment teams with minimal disruption. Work closely with the Business and IT Stakeholders to ensure that business continuity and disaster recovery plans are updated. Executive Communication & Reporting: Create, collate, and provide clear, concise, and data-driven status updates to Program Leadership and key Business and IT stakeholders. Present regular deployment plans updates, cutover strategies, and risk mitigation strategies in front of C-Level Stakeholders. V-Soft Consulting Group is recognized among the top 100 fastest growing staffing companies in North America, V-Soft Consulting Group is headquartered in Louisville, KY with strategic locations in India, Canada and the U.S. V-Soft is known as an agile, innovative technology services company holding several awards and distinctions and has a wide variety of partnerships across diverse technology stacks. As a valued V-Soft Consultant, you’re eligible for full benefits (Medical, Dental, Vision), a 401(k) plan, competitive compensation and more. V-Soft is partnered with numerous Fortune 500 companies, exceptionally positioned to advance your career growth. V-Soft Consulting provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. #LI-ZA1