Our leading public sector client is  seeking an experienced Program Deployment & Cutover Lead to oversee deployment execution, cutover planning, and hypercare transition within a large-scale ERP or enterprise transformation program. The ideal candidate will bring strong leadership in orchestrating complex go-live activities, coordinating cross-functional teams, and ensuring smooth transition from program to operations with minimal disruption.

This is a 1 year term reporting to the Downtown Toronto office. 

Key Responsibilities

Deployment & Cutover Planning

• Develop, own, and maintain a detailed deployment and cutover plan, including dress rehearsals, mock conversions, data loads, environment readiness, business validation, and final cutover execution.

• Partner closely with transformation and implementation teams to ensure alignment across all deployment streams.

Orchestration & Leadership

• Coordinate cross-functional stakeholders (Business, IT, Data, Infrastructure, Vendors) to manage dependencies and ensure on-time execution of cutover milestones.

• Collaborate with Release Leads and Program Leadership to secure appropriate resourcing and support.

Dress Rehearsals & Mock Runs

• Lead end-to-end simulations to validate timing, data accuracy, and overall readiness.

• Identify and proactively resolve issues prior to go-live.

Data Loads & Validation

• Oversee data migration and validation activities across master, transactional, and configuration datasets.

• Ensure business engagement and signoff on data quality and readiness.

Risk & Contingency Management

• Track deployment RAID items (Risks, Assumptions, Issues, Dependencies).

• Develop and maintain contingency and fallback plans to safeguard business continuity.

Go/No-Go Governance

• Lead structured Go/No-Go readiness reviews with Business and IT leadership.

• Ensure all checkpoints and quality gates are achieved prior to cutover execution.

Hypercare, BCP & Transition to Sustainment

• Oversee post go-live hypercare support and transition planning to operations and sustainment teams.

• Partner with Business and IT stakeholders to ensure Business Continuity and Disaster Recovery (BCP/DR) plans are fully updated and validated.

Executive Communication & Reporting

• Deliver concise, data-driven deployment status updates to program leadership and executive stakeholders.

• Present cutover strategies, readiness summaries, and risk mitigation plans to C-level audiences.

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Must-Have Qualifications

• 10+ years of program or project management experience, with 5+ years in deployment and cutover leadership for large-scale ERP or enterprise transformation programs.

• Proven experience with ERP solutions such as SAP, Oracle, or Microsoft Dynamics.

• Experience deploying enterprise platforms such as BY, Manhattan WMS, GK POS, or Adobe (or similar).

• Exposure to Supply Chain, Merchandising, Finance, POS, and Warehouse Management systems within retail environments.

• Strong understanding of change management and business readiness processes.

• Exceptional communication, stakeholder management, and presentation skills.

• Professional certification such as PMP, PRINCE2, or equivalent.

We’re an equal opportunity employer committed to increasing diversity and inclusion in today’s workforce. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. Minorities, women, LGBTQ candidates, and individuals with disabilities are encouraged to apply. If you require an accommodation, please review our accessibility policy and reach out to our accessibility officer with any questions.