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.

• Manage Microsoft 365 / Entra  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 cloud managed 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

• 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 compliance related policies and documentation

• 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 company owned mobile devices
• Manage IT asset inventory across all locations

• 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

• 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

• 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

• 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  (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 configuration (Sophos a strong plus)
• Solid network fundamentals: LAN/WAN, switches, VLANs and firewall management
• Comfortable deploying and supporting Windows PCs, laptops and common peripherals
• Experience with warehouse technology: barcode scanners, thermal label printers and mobile devices
• Valid driver's license and willingness to travel throughout New England (firm requirement) travel 4050%
• Strong communication skills — comfortable working with management, auditors and nontechnical staff alike

• Experience in logistics,…