Program Release Lead - Retail Transformation (Greater …, Greater Toronto Area

Location: Toronto, ON, In office 5 days per week Language: English, advanced written and verbal communication required Duration: 6-month contract (open to extension to up to 3 years total) Background Check Requirement: Criminal and Reference check Pay rates: $90-115/HR (relevant to experience) About the Opportunity A major retail transformation program is seeking an experienced Release Lead to support a large-scale enterprise modernization initiative focused on reshaping operations, supply chain capabilities, and technology delivery. This role will play a critical part in orchestrating complex releases across multiple business and IT workstreams, ensuring successful execution within aggressive timelines and evolving business priorities. Working alongside senior leadership, transformation partners, and cross-functional teams, you’ll help drive deployment readiness, cutover execution, and organizational alignment for a high-visibility program impacting enterprise-wide operations. This opportunity is ideal for a strong delivery professional who thrives in fast-paced environments and brings a structured, business-focused approach to large transformation initiatives. What’s In It for You - Join a high-impact transformation program with enterprise-wide visibility and executive engagement - Work alongside experienced business and technology leaders in a collaborative environment - Gain exposure to large-scale retail and supply chain modernization initiatives - Contribute to meaningful organizational change within a complex and evolving business landscape - Be part of a team that values accountability, delivery excellence, and strategic thinking Your Responsibilities - You’ll lead release planning and execution activities across multiple workstreams involving large cross-functional teams - In this role, you’ll manage deployment and cutover strategies, ensuring readiness across business and technical stakeholders - You’ll enforce scope and timeline controls to maintain delivery integrity and prevent scope creep - You’ll oversee RAID management activities, proactively identifying risks, dependencies, and mitigation strategies - In this position, you’ll provide executive-level reporting and communicate project health, milestones, and release readiness updates - You’ll support organizational change management and business readiness efforts throughout the transformation lifecycle - You’ll coordinate delivery using a hybrid Agile and Waterfall methodology approach Skills and Qualifications - 10+ years of progressive project, program, or release management experience within large enterprise transformation environments - Proven experience leading large-scale software deployments, supply chain migrations, or retail transformation initiatives - Strong expertise in deployment planning, cutover strategy, and business transformation delivery - Advanced proficiency with Microsoft Project and structured project planning methodologies - Experience managing teams of 100+ resources across business and IT functions - Exceptional stakeholder management and executive communication skills - PMP or PRINCE2 certification is required - Experience within retail, supply chain, ERP, or enterprise modernization programs is highly preferred - Familiarity with SAP, S4 HANA, BY Product Suite, iCertis, Ariba, or related enterprise retail systems is considered an asset Apply on Kit Job: kitjob.ca/job/2o2uit