Windsor is seeking an experienced Senior Retail IT Helpdesk Technician to serve as the senior operational and technical escalation resource for the Retail Helpdesk during the assigned shift, with primary responsibility for weekend coverage. This position provides day to day shift guidance, maintains continuity when the Retail Helpdesk Supervisor is unavailable, and owns the coordination of store technology work including, but not limited to, new store openings, brand refreshes, equipment deployments, and third party technician dispatches. The role requires strong technical judgement, proactive follow through, clear communication, and the ability to move incidents and project to completion across multiple teams and vendors.

Essential job functions include but are not limited to:

• Serve as the senior escalation point for Retail Helpdesk technicians and store teams during the assigned shift, especially on weekends, resolving issues within scope and escalating appropriately when additional support or approval is required.
• Provide shift level operational coverage by helping prioritize workload, confirming ownership of urgent items, identifying coverage risks, and ensuring open issues have a clear next action and owner.

• Monitor the support queue., calls, and escalations throughout the day; distinguish routine requests from high impact incidents and respond based on business impact, urgency, and established escalation procedures.
• Own advanced troubleshooting and coordination for store technology including point of sale systems, mobile devices, printers, payment peripherals, networks, Wifi, phone systems, and related store equipment.
• Coordinate new store openings, relocations, closures, brand refreshes, and other store projects from equipment staging through installation, validation, turnover, and post-install follow up.
• Schedule and direct third party field technicians and vendors, providing a complete scope of work, store contracts, access requirements, appointment details, and validation criteria before dispatch.
• Follow up on technician dispatches and vendor work until completion; confirm results with the store, collect required notes or photos, document remaining issues, and arrange return visits when necessary.
• Maintain timely, accurate ticket and project documentation, including troubleshooting performed, decisions made, ownership, vendor status, business impact, and the next required action.
• Provide clear written and verbal status updates for high-impact incidents and store projects, including weekend-to-weekday handoffs to the Retail Helpdesk Supervisor and relevant IT teams

Qualifications and Requirements:

• 4-6 years of experience in helpdesk, desktop support, retail technology support, or a comparable customer support role; retail helpdesk experience is strongly preferred
• Ability to remain flexible with work schedules and adjust shifts, hours, or coverage as needed to support business operations, team coverage, store openings, incidents, projects, holidays, and other operational needs
• Demonstrated ability to work independently, make sound decisions, take initiative, and maintain progress without continuous supervision.
• Experience serving as an escalation resource, shift lead, senior technician, or project coordinator is preferred.
• Strong follow-through and organizational skills, with the ability to manage multiple active incidents, dispatches, and store projects while maintaining clear ownership and documentation.
• Working knowledge of retail point-of-sale environments, payment peripherals, Apple and iOS devices, Windows 10 or 11, Active Directory, Google Workspace, basic networking, Wi-Fi, access points, and phone systems.
• Experience with mobile device management, ticketing systems, remote support tools, asset management, and vendor or field-technician coordination is preferred.
• Ability to assess business impact, recognize store-down or revenue-impacting conditions, and follow established notification and escalation requirements.
• Excellent verbal and written communication skills, including the ability to explain technical issues clearly to non-technical store teams and provide concise status updates to IT partners and leadership.