IT Lead, IT Support, Systems Administrator

Craving a challenging and rewarding career in a place you actually love? Perfect. Demetres was founded in 1989, and we're the premiere destination for desserts in Toronto. With our 12 restaurant locations, 5 ice cream boutiques, our own central production facility, and a growing retail CPG presence, we are innovators in our field. For decades we have set the very definition of dessert experience.

Our greatest years are yet to come, and we're looking for the best people to take us there.

Behind every perfectly plated dessert is a quiet army of technology that just has to work. We're looking for an IT Lead who will own that entire environment across our Demetres restaurants, our Scooped by Demetres QSR ice cream shops, our central production facility, and our corporate head office.

This is a high ownership, deeply hands-on role for a technical generalist. It's the POS terminal that drops offline at 9:30 PM on a packed Saturday. It's the new GM who needs every account provisioned before their first shift. It's the Meraki access point at a new store that has to be configured, racked, and live before opening day. It's the Google Sheets script that finally automates a report someone has been rebuilding by hand for two years.

We need someone who can find them, fix them, and design the systems that keep them from coming back.

You'll work in a small IT team alongside our existing IT teammate, and partner closely with our core maintenance and operations teams. You'll report into senior leadership, and you'll be trusted to ensure everything runs efficiently.

• Own end‑user support across the full IT environment. Setup and maintain office and commercial hardware including computers running Windows or Mac, Microsoft 365, Google Workspace, our core SaaS platforms, and network connectivity
• Maintain and support our POS infrastructure (Oracle Simphony), including POS backend servers and front‑of‑house terminals across all locations
• Manage our networks across every site. This includes patch panels, network switches, LAN, wireless access points, and site‑to‑site VPNs running on Cisco Meraki equipment. Maintain proper VLAN segmentation and firewall configuration
• Be available to resolve store issues during restaurant operating hours, including evenings and weekends. The vast majority of these are resolved remotely over Slack or a quick Facetime call.
• Build internal tools and automations to remove manual work. Light code, Python scripts, Google Apps Script, and similar. Support the accuracy and consistency of core data (recipes, inventory, labour rules) across our platforms
• Perform preventative maintenance so that problems are caught before they cost us a service
• Create and maintain SOPs, documentation, and training resources so that our systems are operable by more than one person

• 2+ years in a hands‑on generalist IT role
• Solid networking fundamentals – LAN and wireless design, VLANs, firewalls, cabling, and the practical skills to troubleshoot at each layer
• Light development skills, some familiarity working with Python, Google Apps Script, APIs, SQL, or similar. Sufficient to build small internal tools and automations
• Access to reliable transportation; this role is based out of our head office but requires regular travel to our locations across the GTA
• Flexibility to occasionally work evenings and weekends when issues require it

• You fix things permanently. When something breaks twice, you treat the second time as a design problem, not a support ticket
• You think in systems and SOPs, not heroics. The goal isn't to be the only person who knows how something works
• You're equally happy in a network closet, in a terminal window, and in a meeting with senior leadership
• You actually like restaurants and care that they run well. You understand that an IT problem at 8 PM on a Saturday is a guest‑experience problem

• Real autonomy over the IT environment for an entire vertically integrated dessert company
• Variety – no two days are the same, and the surface area is genuinely large
• A collaborative,…