Director, Point of Sale & Payments

Loblaw Companies Limited•Brampton, ON

3d•CA$128,000 - CA$176,000

About The Position

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.

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

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