Loblaw Companies

Director, Point of Sale & Payments

Loblaw Companies$128K — $176K *
Retail & Consumer Goods
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 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 POS platforms within overall store systems architecture.
  • Experience with self-checkout systems and retail transaction flows.
  • Familiarity with PCI compliance and payment security technologies.

Responsibilities

  • Develop and execute the POS technology roadmap in alignment with retail strategy.
  • Coordinate with leadership, stakeholders, and vendors to prioritize POS initiatives.
  • Lead lifecycle management of POS platforms including backlog planning and upgrades.
  • Oversee onboarding and configuration of new store technology.
  • Ensure integration of POS systems with back-office, payment processing, and inventory platforms.
  • Manage payment technologies including mobile payments and digital wallets.
  • Establish KPIs to measure POS performance and compliance with industry standards.
Full Job Description
The Impact You'll Make

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.

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


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.

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About Loblaw Companies

Loblaw Companies Limited is a Canadian food retailer that encompasses 22 brands, including Loblaws, No Frills, Real Canadian Superstore, and Shoppers Drug Mart. The company was founded in 1919 by Theodore Loblaw and J. Milton Cork. Loblaw Companies Limited is the largest food retailer in Canada, with over 1,050 corporate and franchised stores across the country. The company also operates a loyalty program called PC Optimum, which allows customers to earn points on purchases that can be redeemed for discounts on future purchases.
Learn more about Loblaw Companies
Size
215,000 employees
Industry
NASDAQ

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