Help Desk Technician

Highland Ventures is a family-owned national venture management company focused on strategically developing and operating businesses centered around real estate. Our portfolio includes Hoogland Restaurant Group (the largest franchisee of Marco's Pizza with 130+ locations), Legacy Commercial Property (owning and managing over 700 commercial properties), Highland Pure Water & Ice (24/7 kiosks with over 70 locations in 10+ states), and Intune Physical Therapy (a physical therapy brand currently being built from the ground up).

About the role

The Help Desk Technician plays a critical role in maintaining system reliability and ensuring our internal teams across Highland Ventures’ portfolio companies receive timely, professional technical support. This position requires a balance of technical expertise, strong communication skills, and a client-focused approach. The ideal candidate will demonstrate solid problem-solving abilities, excellent customer service, and a commitment to delivering quality technical solutions. This is a generalist role on a small, lean IT team handling the full mix of work that comes through our ticketing system, from process-driven restaurant tasks to desktop troubleshooting at our physical therapy clinics to user access provisioning across the company.

Responsibilities

• Serve as the first point of contact for users seeking technical assistance via phone, email, ticketing system, or remote session
• Diagnose and resolve technical problems using diagnostic tools and systematic troubleshooting approaches
• Communicate technical solutions clearly and effectively, adjusting complexity based on the user’s technical knowledge
• Provision and manage user access: account creation, permissions changes, role transitions, and terminations across the company’s business lines
• Support restaurant operations, including menu changes, order management system tickets, and point-of-sale equipment issues at our HRG Pizza locations
• Provide front-line network and connectivity support: Meraki diagnostics, ISP coordination, Wi-Fi and printer issues at remote sites
• Administer Microsoft 365 accounts, mailboxes, and shared resources, with basic Exchange, Teams, and SharePoint support
• Support healthcare clinic workstations for Intune Physical Therapy, handling patient data with appropriate attention to security and HIPAA requirements
• Escalate complex issues to appropriate technical teams while maintaining clear communication with users throughout resolution
• Document solutions and troubleshooting steps in the knowledge base to improve self-service options and team efficiency
• Maintain current technical knowledge through ongoing learning and professional development
• Support users across multiple Highland Ventures companies including Legacy Commercial Property, Hoogland Restaurant Group, Intune Physical Therapy, and Highland Pure Water
• Contribute to project work as capacity permits: onboarding new locations, hardware refresh projects, and rollouts of new tools

Requirements

• Minimum 1-3 years of hands-on help desk or technical support experience in a professional environment
• Strong understanding of networking fundamentals and ability to diagnose network-related issues
• Proficiency with both Windows PC and Mac operating systems
• Experience with Microsoft Active Directory and user account management
• Demonstrated problem-solving abilities with a methodical approach to troubleshooting, including comfort working through unfamiliar issues without a runbook for every problem
• Excellent verbal and written communication skills, with ability to explain technical concepts to non-technical users
• Strong customer service orientation and professional demeanor when interacting with users at all levels
• Experience with ticketing systems (ServiceNow, Jira, or similar platforms), including clean documentation and ticket discipline
• Reliable schedule and attendance: a small help desk team depends on predictable coverage
• Flexibility to work various shifts including some evenings and weekends as needed, with periodic on-call coverage

Preferred Skills

• Microsoft Entra ID (Azure AD) and Microsoft Intune
• Cisco Meraki network equipment
• Apple Business Manager
• Electronic Health Records (EHR) systems
• Restaurant Point of Sale (POS) systems
• 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

This is a full-time, on-site position based in Brentwood, TN. The position primarily involves evening and weekend shifts to ensure comprehensive coverage during all business operating hours. In addition to regular shifts, employees may be required to be on call monthly, ready to provide prompt support outside of standard operating hours when necessary.