IT Support Specialist – Head Office

Jobtailor; Toronto; On-site; CAD 70,000 - 90,000; Full time

Job summary

Jobtailor is seeking an experienced Front-Line Technical Support specialist to assist onsite and remote users across multiple retail locations. You will manage POS and ERP systems, deploy HP hardware, and address networking and MDM needs to ensure reliable store operations.

The role requires hands-on experience with Windows, SQL Server, AD/AAD, and a willingness to travel for store openings and upgrades. Weekend and after-hours support may be required.

Qualifications

• Minimum of five years of end-user and remote technical support experience.
• Proven hands-on experience supporting ERP and retail POS environments.
• Strong Active Directory and Azure AD (Entra ID) skills; Windows OS proficiency and SQL Server knowledge.

Responsibilities

• Provide front-line technical support to onsite and remote end users.
• Support POS systems, cash registers, and ERP environments.
• Install, configure, and troubleshoot HP Retail hardware and devices.
• Support network printers and resolve connectivity issues.
• Troubleshoot VLANs, SSL tunneling, and SSL clients.
• Provide support during weekends, holidays, and after hours as required.
• Travel between retail locations to support operations and openings.
• Assist with setup and deployment of new retail stores.
• Support MDM solutions across devices (ManageEngine, Apple, Android).

Skills

End-User Support

Remote Support

POS/ERP Troubleshooting

AD Management

SQL Server

Windows OS

Networking

MDM (mobile)

Tools

ManageEngine MDM

Apple Device Management

Android Device Management

SQL Server

Job description

• Provide front-line technical support to onsite and remote end users
• Support Point-of-Sale (POS) systems, cash register environments, and ERP systems
• Install, configure, and troubleshoot HP Retail hardware, including touchscreens, receipt printers, barcode scanners, and HP/Dell desktops and laptops
• Support network printers and resolve general network connectivity issues
• Troubleshoot and support VLANs, SSL tunneling, and SSL clients
• Provide technical support to retail stores during weekends, holidays, and outside regular business hours as required
• Travel between retail locations to support day-to-day operations and new store openings and projects
• Assist with setup and deployment of new retail stores
• Support Mobile Device Management (MDM) solutions, including ManageEngine MDM, Apple device management, and Android device management

Requirements

• Minimum of proven five (5) years of experience providing end-user and remote technical support (mandatory)
• Proven hands-on experience supporting ERP systems and retail Point-of-Sale (POS) environments (mandatory)
• Experience managing Active Directory (AD) and Azure Active Directory (AAD)/Microsoft Entra ID
• Strong knowledge of Microsoft Windows operating systems, including installation, troubleshooting, and administration
• Extensive hands-on experience with Microsoft SQL Server (STD\Express)
• Strong understanding of database architecture, performance tuning, query optimization, and troubleshooting (mandatory)
• Experience supporting and troubleshooting network printers
• Solid understanding of networking concepts, including VLANs, routing, SSL tunneling, SSL clients, switching, Wi-Fi, and firewall policies
• Ability and willingness to work flexible hours, including weekends, holidays, and on-call support when required
• Valid driver's license with the ability to travel between retail locations as needed

Core Competencies

Demonstrates extensive experience in providing technical support for Point-of-Sale (POS) systems and ERP systems, with strong skills in troubleshooting hardware and network issues. Proficient in managing Active Directory and Azure Active Directory, with a solid understanding of database architecture and networking concepts.

Highest-signal resume keywords

• End-User Technical Support
• Point-of-Sale (POS) Systems
• ERP Systems
• Active Directory (AD) Management
• Microsoft SQL Server

Hard Skills

• Technical Support
• Troubleshooting
• Database Architecture
• Network Connectivity
• VLANs
• SSL Tunneling
• Microsoft Windows
• Performance Tuning
• Query Optimization
• Mobile Device Management (MDM)

Soft Skills

• Flexibility
• Problem-Solving
• Communication

Certifications & Qualifications

• Valid Driver's License

Industry Keywords

• Retail
• Technical Support
• Network Printers
• Onsite Support
• Remote Support

Tools & Technologies

• HP Retail Hardware
• ManageEngine MDM
• Apple Device Management
• Android Device Management