IT Helpdesk & Network Support Specialist

Drake & Associates is seeking a customer-focused IT Helpdesk & Network Support Specialist to support our team of 60 employees across our Waukesha and Mequon offices. In this role, you will serve as the primary technical point of contact for employee onboarding, hardware/software troubleshooting, and macOS endpoint management. Additionally, you will manage local office networking (LAN/Wi-Fi/VPN) and support user access across our cloud-first ecosystem built on Google Workspace, GCP, and Salesforce.

Our environment is 100% Microsoft-free. The ideal candidate thrives in a Mac-centric, Google-native environment and possesses a strong grasp of core networking fundamentals and identity management.

Key Responsibilities

End-User Support & macOS Administration

• Provide tier-1 and tier-2 technical support for staff across the Waukesha and Mequon locations via ticketing, Slack, or in person.


• Provision, deploy, and manage Apple hardware (MacBooks, displays, mobile devices) using Apple Business Manager and MDM solutions.


• Administer user accounts, security groups, and Multi-Factor Authentication (MFA) within Google Workspace SSO and Google Identity-Aware Proxy (IAP).


• Troubleshoot productivity tools, Google Calendar syncs, and core business applications (Salesforce, BambooHR, ActiveCampaign).


• Maintain hardware/software asset inventories and assist with employee onboarding/offboarding workflows in BambooHR.

Network & Cloud Infrastructure

• Configure, monitor, and troubleshoot office local area networks (LAN), Wi-Fi access points, routers, and VPN connectivity across office sites.


• Manage TCP/IP configurations, DHCP reservations, DNS records, VLANs, and firewall rules.


• Assist in monitoring basic cloud networking and access controls within Google Cloud Platform (GCP), including VPC serverless connectors and IAP ingress.


• Coordinate with internet service providers (ISPs) and network hardware vendors to resolve line drops and outages promptly.


• Maintain server room cabling, patch panels, and local network equipment.

Security & Documentation

• Enforce corporate security policies across endpoints and SaaS applications, ensuring MFA compliance and secure credential management via Secret Manager.


• Manage developer/user access permissions for GitHub and internal application environments.


• Maintain clear technical documentation, Standard Operating Procedures (SOPs), and end-user self-help guides.

Required Qualifications

• Experience: 2–4 years of hands-on Technology experience in an IT Helpdesk, Desktop Support, or Service Desk role supporting a macOS environment.


• Identity & OS: Strong proficiency with Google Workspace Administration (SSO/MFA) and Apple Business Manager (MDM).


• Networking Fundamentals: Solid understanding of TCP/IP, DNS, DHCP, VLANs, Subnetting, VPNs, and Wi-Fi standards (802.11ax/ac).


• Hardware: Experience troubleshooting Apple Mac hardware, peripherals, office switches, routers, and Ethernet cabling.


• Soft Skills: Outstanding communication and interpersonal skills, with patience for explaining technical concepts to non-technical staff.

Preferred Qualifications

• SaaS & Cloud: Familiarity with Google Cloud Platform (GCP) basics, Salesforce administration, and GitHub user management.


• Certifications: CompTIA Network+, CompTIA A+, Apple Certified Support Professional (ACSP), or Cisco Certified Support Technician (CCST).


• Security: Understanding of Zero Trust architecture, Google IAP, and endpoint protection software.


• Software & Web Development: Experience with software or web development is a plus.


• AI Tools: Experience using AI tools to work more efficiently.

Physical Requirements & Working Conditions

• Ability to lift, transport, and rack equipment up to 50 lbs.


• Flexibility to work on-site between the Waukesha and Mequon offices as needed for hardware setup and network maintenance.