Manager of Information Technology; IT Manager

Description

Kelli’s is looking for a hands‑on Manager of Information Technology to support our growing organization and retail operations. This position is responsible for the technology, infrastructure, point‑of‑sale systems, and IT operations that keep our corporate office, distribution centre, and retail locations running effectively.

This is a working management role for someone who enjoys being hands‑on and solving problems—not simply delegating them. You will configure systems, support new store openings, troubleshoot networks and POS issues, administer Microsoft 365 and servers, and serve as a senior technical resource for the organization.
Position is based in‑house M‑F.

• Lead the technology setup and implementation for new retail store openings, including POS systems, registers, networks, wireless, and related equipment.
• Configure and administer NCR Counterpoint point‑of‑sale systems across multiple locations.
• Troubleshoot POS, payment, network, connectivity, and system issues and identify root causes.
• Manage payment terminals and related hardware, including deployment, replacement, inventory, and decommissioning.
• Administer Microsoft 365, Entra , Exchange Online, SharePoint, Teams, and endpoint policies
  .
• Manage Windows Server, Hyper‑V, Active Directory/Entra , networking, firewalls, VPNs, wireless systems, and site connectivity.
• Manage company endpoints, including imaging, deployment, patching, monitoring, antivirus, and equipment refreshes.
• Support warehouse technology, including handheld devices and barcode scanning equipment.
• Maintain backup, recovery, and disaster‑recovery processes and conduct periodic restore testing.
• Implement assigned IT security and compliance controls, including vulnerability management, patching, MFA, access reviews, and audit requirements.
• Support PCI DSS requirements related to our retail and payment environments.
• Partner with Human Resources on employee onboarding, system access, and timely deprovisioning.
• Serve as the second‑level technical escalation for the Service Desk.
• Work closely with store operations, Cloverkey leadership, development, vendors, and hospital partners to resolve technology issues.
• Manage day‑to‑day technology vendor relationships, service tickets, equipment, licences, warranties, and subscriptions.
• Maintain accurate IT documentation, procedures, and runbooks.
• Travel to retail locations for installations, new store openings, go‑lives, and post‑opening support.

Requirements

• 5+ years of progressive hands‑on IT experience, including experience in a lead, supervisory, or senior technical role.
• Experience supporting a multi‑site environment, preferably retail, restaurant, healthcare, or another distributed operation.
• Hands‑on experience with:
  Windows Server and virtualization
• Active Directory and/or Entra 
• Microsoft 365 administration
• TCP/IP, VLANs, routing, switching, wireless, firewalls, and VPNs
• Enterprise endpoint management
• Experience administering a retail point‑of‑sale system and configuring a new location
• NCR Counterpoint experience is strongly preferred.
• Experience with payment terminals and an understanding of PCI DSS requirements.

• Direct NCR Counterpoint administration experience.
• Experience opening new retail locations.
• Experience working in a hospital or healthcare facility environment.
• Experience with CIS Controls, NIST, PCI DSS, or other formal security frameworks.
• Experience with Jira and Confluence.
• Experience with remote monitoring and management platforms.
• Experience supporting warehouse handheld devices, barcode scanning, or warehouse management technology.
• CompTIA, Microsoft, Cisco, ITIL, or other relevant certifications.
• Bachelor’s degree in Information Technology, Computer Science,…