Director, POS & Payments Modernization

Loblaw Companies Limited; Brampton; On-site; CAD 128,000 - 176,000; Full time

Job summary

Loblaw Companies Limited is seeking a Director of Point of Sale & Payments to lead strategy, performance, and modernization of checkout and payment tech across Canada’s store network. You will guide POS platforms, ensure reliability, and drive security and scalability.

You’ll collaborate with store operations, UX, engineering, and vendors to align roadmaps, manage budgets, and deliver a seamless customer experience at scale.

Qualifications

• 8+ years of experience in retail technology, payments, or POS 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

Responsibilities

• 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

Skills

POS strategy

Retail technology

Payment platforms

Self-checkout systems

PCI compliance

Project management

Stakeholder management

Vendor management

Leadership

Cross-functional collaboration

Job description

Loblaw Companies Limited is seeking a Director of Point of Sale & Payments to lead strategy, performance, and modernization of checkout and payment tech across Canada’s store network. You will guide POS platforms, ensure reliability, and drive security and scalability.

You’ll collaborate with store operations, UX, engineering, and vendors to align roadmaps, manage budgets, and deliver a seamless customer experience at scale.