Senior Retail IT Helpdesk

Windsor-Fashions-LLC; Valla (CA); On-site; USD 70,000 - 95,000; Full time

Job summary

Windsor-Fashions-LLC is seeking an experienced Senior Retail IT Helpdesk Technician to serve as the senior escalation resource for the Retail Helpdesk during the weekend shift. The role focuses on guiding the team, maintaining continuity, and coordinating store technology deployments.

Responsibilities include advanced troubleshooting for POS systems, networks, mobile devices, printers, and related hardware; coordinating third-party technicians; and delivering clear status updates to IT partners

Qualifications

• 4-6 years of experience in helpdesk or retail technology support.
• Experience serving as escalation resource or shift lead.
• Strong written and verbal communication.
• Ability to coordinate store technology initiatives.
• Flexibility for weekend coverage and varying shifts.

Responsibilities

• Serve as senior escalation point during the assigned shift, especially weekends.
• Provide shift level operational coverage and ownership.
• Monitor support queue and differentiate high-impact incidents.
• Coordinate store technology work including POS, mobile devices, printers, networks.
• Schedule and direct third-party technicians and vendors.
• Maintain accurate ticket and project documentation.
• Provide status updates to IT partners and leadership.
• Handoff weekend to weekday IT teams.

Skills

Helpdesk leadership

Retail technology

Escalation management

Vendor coordination

Communication

Incident management

Tools

Active Directory

Google Workspace

Windows 10/11

POS systems

Printer/Network hardware

Job description

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 teamsQualifications 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 preferredAbility 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 needsDemonstrated 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.Customer-oriented, patient, dependable, and able to provide calm direction during urgent or high-pressure incidents.Ability to work the regular Saturday-Wednesday schedule, with Thursday and Friday as the regular days off. Additional early, late, holiday, or overtime coverage may be required based on store openings, incidents, and business needs.Ability to coordinate remote and on-site technicians for store turnups and other scheduled technology workProficiency in English is required; Spanish is a plus.