Director, Point of Sale & Payments

Come make your difference in communities across Canada, where authenticity, trust and making connections is valued – as we shape the future of Canadian retail, together. Our unique position as one of the country's largest employers, coupled with our commitment to positively impact the lives of all Canadians, provides our colleagues a range of opportunities and experiences to help Canadians Live Life Well®.

At Loblaw Companies Limited, we succeed through collaboration and commitment and set a high bar for ourselves and those around us. Whether you are just starting your career, re-entering the workforce, or looking for a new job, this is where you belong.

The Director, Point of Sale & Payments
is responsible for the strategy, performance, and evolution of all checkout and payment technologies across the company’s national store network. This role oversees traditional checkout lanes, self-checkout solutions, and payment platforms to deliver a seamless, secure, and efficient customer transaction experience. Reporting to the Sr. Director of Stores Front End Technology, the Director will lead the modernization and optimization of point-of-sale systems while ensuring operational reliability across thousands of checkout endpoints.

The role requires strong leadership across technology, store operations, payments, and vendor ecosystems to support innovation and scalability.

• Develop and execute the POS technology roadmap in alignment with overall retail strategy
• Coordinate with leadership, business stakeholders, technology peers and vendors to prioritize POS initiatives.
• Lead the lifecycle management of POS platforms including backlog planning, upgrades, and modernization initiatives.
• Oversee new store technology onboarding and configuration readiness.
• Ensure the availability, performance, and integration of POS systems with back-office, payment processing, inventory, and loyalty platforms
• Manage versioning, upgrades, patches, and technical documentation
• Manage payment technologies including card processing, gift cards, mobile payments, digital wallets, and emerging payment methods
• Provide leadership for troubleshooting, incident response, and vendor escalation paths when POS issues affect store operations.
• Partner with support teams to prioritize product development that reduces incidents
• Partner with specialists and store users for training and adoption of best practices.
• Work with UX, engineering, product, and operations teams to define requirements and drive solution design
• Manage relationships with any external POS hardware, software, and payment solution vendors
• Establish KPIs and metrics to measure POS performance, reliability, and impact on sales/operations
• Ensure compliance with industry standards, payment security best practices and data privacy
• Ensure compliance with security requirements

• 8+ years of experience in retail technology, payments, or point-of-sale systems.
• 5+ years in a leadership role overseeing enterprise technology platforms or large-scale store technology environments.
• Proven track record in developing POS strategy through technical delivery and operations
• Familiarity with modern POS platforms (cloud, APIs etc)
• Deep understanding of the role of POS platforms in the overall store systems architecture and integration patterns
• Experience with self-checkout systems and retail transaction flows.
• Familiarity with PCI compliance, payment security, and fraud prevention technologies.
• Strong project management, risk and stakeholder management skills with experience working in a cross-functional environment
• Experience managing external providers, including managing budgets and contracts

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