IT Retail Systems Support Analyst

Sleep Country

Job Description

We are seeking a highly skilled and motivated IT Retail Systems Support Analyst to support and drive the successful rollout of our new Point of Sale (POS) platform. The IT Retail Systems Analyst will be responsible for supporting all aspects of the rollout activity which includes establishing a depot service staging and deployment process, executing the rollout plan in coordination with external partners, and performing post-implementation troubleshooting and support.. The ideal candidate should possess a deep understanding of retail systems, excellent organizational skills, and proven experience in executing large-scale rollouts.

Reporting to the Manager, Infrastructure & Operations, responsibilities of this role will include but are not limited to:

  • POS Staging and Rollout: Support the planning, testing, and deployment of Oracle Retail Xstore across our retail locations. Collaborate with the IT team, vendors, and stakeholders to ensure a smooth and efficient rollout while adhering to project timelines and budgets.
  • Retail Infrastructure Management: Oversee the operation and maintenance of retail systems infrastructure, including Meraki SDWAN, RF scanners, Point of Sale registers, video surveillance equipment, and PED payment solutions. Implement proactive monitoring and troubleshooting strategies to ensure optimal system performance and minimize downtime.
  • Project Leadership: Effectively lead cross-functional teams through all phases of large-scale technology deployments. Communicate project status, risks, and milestones to stakeholders and senior management. Proactively address any challenges that may arise during the implementation process.
  • Technical Support and Issue Resolution: Provide timely and efficient technical support to retail locations regarding system issues, hardware malfunctions, and software updates. Troubleshoot and resolve incidents to minimize disruptions to business operations.
  • Documentation and Training: Create comprehensive documentation for retail systems, procedures, and configurations. Develop training materials and conduct workshops to educate internal helpdesk staff on the effective utilization and troubleshooting of technology systems.
  • Vendor Management: Engage with vendors and third-party service providers to ensure compliance with service level agreements and resolve escalated issues promptly. Evaluate and recommend new technologies and solutions that align with the organization’s business objectives.
  • Additional Considerations: Willingness to travel to various retail locations for system implementation and maintenance. Flexibility to work outside standard business hours when required, including weekends and evenings on occasion, to accommodate project deadlines and resolve urgent issues.

    This is a hybrid role involving both remote and on-site collaboration out of our Brampton office.


  • Education: University or College degree in Information Technology, Computer Science, or a related field.
  • Experience: Proven experience (5+ years in a similar role) which includes successful staging and deployment of technology solutions within a retail environment. Prior experience managing retail infrastructure components such as Meraki SDWAN, VOIP telephony systems, RF guns, Point of Sale registers, video surveillance equipment, and Pin-pad hardware is essential.
  • Knowledge or experience supporting Oracle Retail Xstore POS is considered a significant asset.
  • Leadership and Communication: Strong presentation and leadership skills, with the ability to lead cross-functional teams and effectively communicate technical concepts to non-technical stakeholders.
  • Organization and Time Management: Exceptional organizational skills with the ability to manage multiple projects and deadlines simultaneously.
  • Problem-Solving Skills: Demonstrated ability to identify and resolve complex technical issues efficiently.
  • Retail Experience: Previous experience in a retail or similar environment is highly desirable.
  • Large-Scale Rollouts: Proven track record of successful large-scale technology rollouts from previous employment.

Additional Information

Why members of our Corporate team love working at Sleep Country Canada/Dormez-vous?:

  • This is not a job but a CAREER with opportunities for growth and advancement
  • Diverse and inclusive work environment
  • We will invest in you and provide extensive training, mentoring and continuous development
  • Access to training and development platforms
  • Full medical, dental benefits and a Deferred Profit Sharing Program
  • Annual Wellness Credit for any products/services that improve your health and well-being, ie., health assessments, nutrition counselling, hiking shoes, a yoga outfit or fitness equipment!
  • Associate Discount Program where you will be able to enjoy some of the world’s best sleep products
  • Maternity/Parental leave top up benefits
  • Tuition Reimbursement Program that covers professional AND personal development
  • Long service awards, celebrations and other social events
  • Associate Referral Program
  • Paid day off to volunteer at your local charity of choice
  • Recognized as one of Canada’s Most Admired Corporate Cultures in 2022 by Waterstone Human Capital

Commitment to Equity, Diversity, Inclusion & Belonging (EDI&B)

At SCC/DV, we are committed to building a company culture of inclusion and diversity where differences are embraced and valued, this allows us to better understand and meet the needs of our customers and the communities we serve. We want to ensure every job applicant is treated fairly and with respect regarding race, national or ethnic origin, religion, age, gender, sexual orientation, or disability.

About Sleep Country Canada/Dormez-vous?

Sleep Country is Canada’s leading specialty sleep retailer with a purpose to transform lives by awakening Canadians to the power of sleep.  Sleep Country Canada operates under the retailer banners; Sleep Country, Dormez-vous, Endy, Hush, Silk & Snow and most recently acquired, Casper Canada.  The Company has omnichannel and ecommerce operations including 289 corporate-owned stores and 20 distribution centers warehouses across Canada.  Recognized as one of Canada’s Most Admired Corporate Cultures in 2022 by Waterstone Human Capital, Sleep Country is committed to building a company culture of inclusion and diversity where differences are embraced and valued. The Company actively invests in its sleep ecosystem, innovative products, world-class customer experience, communities and its people.  For more information about Sleep Country, please visit www.sleepcountry.ca.


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