Director, Point of Sale & Payments

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

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 Impact You'll Make

The Director, Point of Sale & Paymentsis 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.

What You’ll Do

• 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

What You'll Bring

• 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

Our commitment to Sustainability and Social Impact is an essential part of the way we do business, and we focus our attention on areas where we can have the greatest impact. Our approach to sustainability and social impact is based on three pillars – Environment, Sourcing and Community – and we are constantly looking for ways to demonstrate leadership in these important areas. Our CORE Values – Care, Ownership, Respect and Excellence – guide all our decision-making and come to life through our Blue Culture. We offer our colleagues progressive careers, comprehensive training, flexibility, and other competitive benefits – these are some of the many reasons why we are one of Canada’s Top Employers, Canada’s Best Diversity Employers, Canada’s Greenest Employers & Canada’s Top Employers for Young People.

We are looking for varied perspectives which include diverse experiences that we can add to our team.

We have a long-standing focus on diversity, equity and inclusion because we know it will make our company a better place to work and shop. We are committed to creating accessible environments for our colleagues, candidates and customers. Requests for accommodation due to a disability (which may be visible or invisible, temporary or permanent) can be made at any stage of application and employment. We encourage candidates to make their accommodation needs known so that we can provide equitable opportunities.

Please Note

Candidates who are 18 years or older are required to complete a criminal background check. Details will be provided through the application process.

Hiring Range / Échelle Salariale à L’embauche

$128,000.00 - $176,000.00 / 128.000,00$ - 176.000,00$ (per year / par an) A candidate’s experience and knowledge as well as the geographical region in which the position is located may be factored into the pay a candidate receives for this position. This posting is for an existing vacancy. The Company uses artificial intelligence for the purpose of screening, assessing and/or selecting applicants for this position. / L’expérience et les connaissances d’un candidat ainsi que la région géographique dans laquelle le poste est situé peuvent être prises en compte dans la rémunération qu’un candidat reçoit pour ce poste. Cette offre d’emploi concerne un poste vacant existant. L’entreprise utilise l’intelligence artificielle dans le but de filtrer, d’évaluer et/ou de sélectionner les candidats à ce poste.