Help Desk Technician - Onsite

Highland Ventures is hiring an On-site Help Desk Technician in Brentwood, TN. This full-time role supports multiple business lines and helps keep restaurants and clinics running smoothly, while you work hands-on with networking, devices, and Microsoft 365. If you enjoy being the first responder for technical issues and take pride in helping users get back to work quickly, this position offers the structure of a dedicated help desk plus variety across locations.

What you’ll do

• Act as the first point of contact for technical assistance via phone, email, ticketing system, or remote session
• Diagnose and resolve problems using diagnostic tools and systematic troubleshooting, documenting what you find
• Explain solutions clearly and adjust the level of detail based on the user’s technical knowledge
• Provision and manage user access including account creation, permission changes, role transitions, and terminations across company business lines
• Support restaurant operations at HRG Pizza, including menu changes, order management system tickets, and point-of-sale equipment issues
• Provide front-line network and connectivity support using Meraki diagnostics, coordinating with ISPs, and handling Wi-Fi and printer issues at remote sites
• Administer Microsoft 365 including accounts, mailboxes, and shared resources, with basic support for Exchange, Teams, and SharePoint
• Support healthcare clinic workstations for Intune Physical Therapy, handling patient data with appropriate attention to security and HIPAA requirements
• Escalate complex issues to the right technical teams while keeping users informed through resolution
• Maintain an accurate, helpful knowledge base by documenting troubleshooting steps to improve self-service and team efficiency
• Support users across Highland Ventures companies including Legacy Commercial Property, Hoogland Restaurant Group, Intune Physical Therapy, and Highland Pure Water
• Contribute to project work as capacity permits, such as onboarding new locations, hardware refresh initiatives, and rollouts of new tools

What you bring

• 1-3 years of hands-on help desk or technical support experience in a professional environment
• Strong networking fundamentals and the ability to diagnose network-related issues
• Proficiency with both Windows PC and macOS
• Experience with Microsoft Active Directory and user account management
• Methodical problem-solving skills, including comfort working through unfamiliar issues without a runbook for every problem
• Excellent verbal and written communication skills, including the ability to explain technical concepts to non-technical users
• A strong customer service orientation and professional demeanor at all user levels
• Experience with ticketing systems such as ServiceNow, Jira, or similar platforms, including clean documentation and ticket discipline
• Reliable schedule and attendance, since a small help desk team depends on predictable coverage
• Flexibility for various shifts including some evenings and weekends, plus periodic on-call coverage

Helpful tools and experience

Highland Ventures uses Microsoft 365, Exchange, Teams, SharePoint, Microsoft Active Directory, ServiceNow, Jira, Meraki, HIPAA, Windows, and macOS. Preferred experience includes Microsoft Entra ID (Azure AD) and Microsoft Intune, Cisco Meraki, Apple Business Manager, EHR systems, restaurant POS systems, and Power Automate or similar automation tools.

Benefits

• Laptop provided
• Group medical, dental, life, and other insurance plans after eligibility requirements are met
• Flex Medical and Flex Daycare spending accounts (FSA)
• 401(k) with 50% match
• Paid time off plus 7 paid holidays

Schedule and work location

This is a full-time, on-site position in Brentwood, TN. The role primarily involves evening and weekend shifts to ensure coverage during business operating hours. Employees may also be required to provide monthly on-call support and respond promptly outside of standard operating hours when needed.