IT System Administrator

Optima Overnight is hiring an IT Systems Administrator who can operate across the full spectrum of our technology needs, from infrastructure administration and security compliance work to hands-on hardware support and field visits across our warehouse network. This is a single, high-impact role: you'll be the go-to technology resource for the organization, building systems and processes that scale with the business. On the operational end, you'll be the primary point of contact for day-to-day hardware support, workstation deployments and end-user assistance, which includes travel to sites throughout New England. On the strategic end, this role contributes to the team responsible for security and compliance, including our SOC 2 program. The right candidate is equally comfortable reviewing firewall policy in the morning and driving to a spoke warehouse in the afternoon to swap out a barcode scanner. Key Responsibilities Infrastructure Administration Manage Microsoft 365 / Entra ID: user lifecycle, licensing, conditional access policies and device compliance Administer Datto RMM: device deployment, patch management and remote support Manage Sophos suite: Endpoint Protection, Email Filtering, and Firewall/router administration, including endpoint enrollment and licensing Oversee Verkada cloudmanaged camera system across all locations Maintain network infrastructure: switches, firewalls, VLANs, ISPs and network provider accounts at all sites Administer VOIP phone system Manage file storage, cloud backup and data retention systems Security & Compliance Support our SOC 2 compliance program: provide documentation and evidence, help enforce policies and support audit readiness Coordinate with the Sophos MDR managed detection and response team; review alerts, incidents and reporting Maintain network and endpoint security posture: firewall policy, access controls and vulnerability management Support disaster recovery and business continuity planning and testing Help maintain security awareness training and compliancerelated policies and documentation Hardware Deployment & Field Support Image, configure and deploy desktop and laptop computers across all locations Set up and support barcode scanners, thermal label printers, laser/inkjet printers and warehouse peripherals Configure and support companyowned mobile devices Manage IT asset inventory across all locations End-User Support Serve as primary point of contact for hardware and software issues across all locations Troubleshoot connectivity, printing, login and application problems Provide remote support using tools such as Tailscale, including remote access to Raspberry Pi 5 devices to troubleshoot connection and hardware issues Support new employee onboarding: account setup, hardware provisioning and orientation Procurement & Vendor Management Source, quote and purchase IT hardware, software and peripherals within budget Track and manage software licenses and renewals (Microsoft 365, Sophos, Datto and others) Manage vendor, ISP and network provider accounts, contracts and billing Strategic Planning & Project Management Provide the CTO with technology roadmap recommendations and cost/benefit analysis Lead technology projects: new location buildouts, client integrations, software evaluations and vendor negotiations Maintain clear documentation of all systems, configurations and IT procedures Required Qualifications Bachelor's Degree in a technical discipline or related field, or equivalent experience 4+ years in a Systems Administration or IT role spanning both infrastructure and handson support Familiarity with security frameworks (NIST CSF, CIS Controls or similar) and how they translate into daytoday controls Handson experience with Microsoft 365 and Entra ID (Azure AD): user lifecycle, device management and conditional access Experience with endpoint management/RMM platforms (Datto or equivalent strongly preferred) Experience with endpoint protection, email filtering and firewall c…

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