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Summary:
Trendsetter Engineering is seeking an IT Support Lead to serve as the hands-on technical backbone of our IT department. This role bridges day-to-day infrastructure operations, project-based deployments, and frontline team leadership. The IT Support Lead will work directly under the IT Manager, taking ownership of network and systems administration tasks while supervising two Helpdesk Support Technicians to ensure timely, high-quality end-user support. This is a working lead position—you will spend the majority of your time solving real technical problems across our Windows-based environment, Cisco network infrastructure, and Microsoft 365 ecosystem, while also coaching and directing helpdesk staff.
Duties and Responsibilities:
- Infrastructure Operations & Maintenance
- Administer and maintain Windows Server environments including Active Directory, DNS, DHCP, Group Policy, and Print Services
- Configure, monitor, and troubleshoot Cisco switching (2960X, stacking, VLANs, trunking) and firewall infrastructure
- Manage VMware virtualization platform including ESXi hosts, vCenter, VM provisioning, snapshots, and resource allocation
- Support and maintain SAN/storage infrastructure, ensuring performance, capacity planning, and backup integrity
- Administer Microsoft 365 services including Exchange Online, SharePoint, OneDrive, and Teams
- Support Azure AD Connect synchronization and hybrid identity management
- Maintain network documentation, configuration baselines, and change logs
- Projects & Deployments
- Assist the IT Manager with planning and executing infrastructure projects such as switch deployments, server migrations, and network upgrades
- Participate in hardware refresh cycles for servers, switches, and end-user devices
- Support rollout and configuration of new technologies and tools as directed
- Test and validate changes in non-production environments before deployment
- Team Leadership & Helpdesk Oversight
- Directly supervise two Helpdesk Support Technicians, providing daily task assignments, coaching, and performance feedback
- Serve as the escalation point for complex helpdesk tickets that exceed Tier 1/Tier 2 scope
- Ensure SLA targets are met for ticket response and resolution times
- Contribute to helpdesk processes, documentation, and knowledge base articles
- Assist with onboarding/offboarding workflows including account provisioning, hardware setup, and security group assignments
- Required Qualifications:
- 3–5 years of hands-on experience in an IT infrastructure or systems administration role
- Solid working knowledge of Windows Server (2016/2019/2022), Active Directory, Group Policy, DNS, and DHCP
- Experience configuring and troubleshooting Cisco switches and firewalls (IOS CLI, VLANs, trunking, ACLs, spanning-tree)
- Familiarity with VMware vSphere/ESXi virtualization environments
- Experience administering Microsoft 365 (Exchange Online, SharePoint, Teams, OneDrive)
- Exposure to Azure AD / Entra ID and hybrid identity sync (Azure AD Connect)
- Familiarity with Azure portal administration, Conditional Access policies, and Microsoft 365 tenant management (user licensing, security groups, compliance settings)
- Understanding of SAN/storage concepts (provisioning, LUN management, basic troubleshooting)
- Experience supporting Windows 10/11 desktops in a domain-joined environment
- Strong troubleshooting methodology and ability to work through complex, multi-system issues
- Previous experience leading, mentoring, or coordinating a small technical team
Preferred Qualifications:
- Industry certifications such as CompTIA Network+, CompTIA Server+, Cisco CCNA, Microsoft 365 Certified, or VMware VCP
- Experience with network monitoring and management tools (SNMP, syslog, SolarWinds, or similar)
- Familiarity with PowerShell scripting for automation and administration tasks
- Experience with backup and disaster recovery solutions (Veeam, Commvault, or similar)
- Exposure to Azure cloud services beyond identity sync (Azure VMs, Azure networking, etc.)
Skills & Attributes:
- Clear communicator who can translate technical issues into business-friendly language for end users and leadership
- Self-motivated and able to manage competing priorities in a fast-paced environment
- Team-oriented leader who leads by example and earns trust through competence
- Detail-oriented with strong documentation habits
- Comfortable working independently while keeping the IT Manager informed of status and issues
Other:
- On-site position with occasional after-hours work for maintenance windows and urgent issues
- May require occasional travel between Trendsetter Engineering facilities
- Participation in on-call rotation for critical infrastructure support
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