Senior Program Manager

About StickerYou StickerYou is a leading global e-commerce company for custom die-cut products such as stickers, labels, decals, temporary tattoos, and more. Our proprietary platform infuses automation technology and creativity to empower anyone to make the best custom products in any size, shape, and quantity. Business and consumers can make their marketing, packaging, décor, or personal expression professional grade. We believe in the enormous power of customization. We are a smart, creative, and passionate group dedicated to growing the most talented and engaging people in Toronto, Canada. We proudly make custom products locally for the global market using software and advanced digital manufacturing. We make what matters stick! The Role We are seeking an experienced Senior Program Manager to lead one of our company's most strategic initiatives: Factory in a Box. Factory in a Box is a cross-functional transformation program that will establish a repeatable manufacturing model capable of being deployed across multiple locations. The program combines manufacturing equipment, software development, cloud technologies, logistics, legal entity creation, reporting, marketing, pricing, and operational readiness into a single integrated program. The Senior Program Manager will be accountable for the successful delivery of the overall program by coordinating multiple workstreams, managing dependencies, facilitating executive decision-making, and ensuring the program achieves its strategic objectives. This role does not require the successful candidate to be the technical expert in every discipline. Instead, they will lead through collaboration with experienced workstream owners who are accountable for delivery within their respective areas. Work Arrangement This is a contract position with a flexible workload that will vary throughout the life of the program based on project phase and business priorities. The expected level of effort may range from approximately 10 hours per week to full time (40 hours per week) during major milestones such as planning, vendor selection, implementation, testing, and go live. Work plans and anticipated hours will be reviewed regularly with the COO to ensure alignment with program priorities and resource requirements. This role is well suited to an experienced Program Manager or independent consultant who enjoys leading complex transformation initiatives while maintaining flexibility in their professional commitments. Responsibilities Program Leadership Lead the Factory in a Box program from initiation through successful implementation. Develop and maintain the integrated program roadmap, master schedule, milestones, and critical path. Ensure alignment across all workstreams and organizational stakeholders. Monitor overall program health, schedule, scope, budget, and quality. Drive accountability while enabling collaboration among workstream owners. Identify and manage cross-functional dependencies. Ensure the program remains aligned with strategic business objectives. Workstream Coordination Coordinate and integrate work across multiple disciplines, including: Equipment and Mechanical Engineering Manufacturing Equipment Procurement Systems Integration Software Development Cloud Migration Reporting and Business Intelligence Logistics and Supply Chain Marketing and Pricing Legal and Corporate Entity Creation Operational Readiness Government Funding and Reporting (e.g., IRAP) Facilitate collaboration across workstreams and ensure that decisions, risks, and dependencies are proactively managed. Governance & Executive Reporting Establish and maintain program governance. Chair weekly cross-functional program meetings. Maintain integrated project plans and dashboards. Prepare executive status reports and Steering Committee presentations. Escalate decisions requiring executive approval. Ensure workstream owners remain aligned with overall program objectives. Risk & Issue Management Maintain comprehensive RAID (Risks, Assumptions, Issues, and Dependencies) logs. Identify risks early and develop mitigation strategies. Resolve cross-functional issues before they impact delivery. Monitor program health and recommend corrective actions. Vendor & Partner Management Coordinate external vendors, consultants, systems integrators, and technology partners. Monitor vendor performance and contractual commitments. Facilitate collaboration between internal teams and external suppliers. Financial Oversight Monitor program budgets, forecasts, and expenditures. Identify financial risks and opportunities. Support business case updates throughout the program lifecycle. Organizational Change & Readiness Coordinate implementation readiness across all business functions. Support communication planning and organizational adoption. Help ensure successful transition into ongoing operations. Required Experience 10+ years of progressively responsible experience in project and program management. Demonstrated success leading large, cross-functional business transformation programs. Experience coordinating initiatives involving multiple business functions and technical disciplines. Strong executive communication and stakeholder management skills. Experience managing complex vendor relationships. Experience facilitating executive steering committees. Strong understanding of dependency management, critical path analysis, and enterprise risk management. Experience managing integrated budgets and program schedules. Preferred Experience Experience in one or more of the following environments: Manufacturing Industrial automation Capital equipment implementation Supply chain or logistics Digital transformation ERP implementations Multi-site operations Software development Cloud technologies Experience in the printing industry is considered an asset but is not required. Diversity & Inclusion StickerYou is strongly committed to Diversity and Inclusion and aims to create a healthy, accessible and rewarding work environment which highlights employees’ unique contributions to our company’s success. If you require accommodation for the recruitment or interview process, please let us know and we will work with you to meet your needs As an equal opportunity employer, we welcome applications from all to help us build a diverse workforce which reflects the diversity of our customers, and communities, in which we live and serve. How We Hire We use AI tools to support our recruitment process, including helping us organize applications and identify early matches based on role criteria. That said, every rejection decision is made by a human. We encourage candidates to apply authentically and avoid relying solely on AI-generated responses, especially during interviews. This posting is for a current, open position within StickerYou . This opportunity is offered through HighlightTA, the on-demand talent team supporting StickerYou's growth. Connect with us and learn more: StickerYou on LinkedIn HighlightTA on LinkedIn