It Systems Administrator

Optima Overnight is looking for 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. You’ll report directly to the CTO and be the go-to technology resource for the organization.

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 means regular travel throughout New England.

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

Oversee Verkada cloud-managed camera system across all locations

Maintain network infrastructure: switches, firewalls, VLANs and ISP relationships at all sites

Administer VOIP phone system

Manage file storage, cloud backup and data retention systems

Security & Compliance

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

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 company-owned 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

Support new employee onboarding: account setup, hardware provisioning and orientation

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

Do you have a valid Driver’s License license?, Do you have experience in Warehouse experience?, Do you have a Bachelor’s degree?, * 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 hands-on support

Familiarity with security frameworks (, NIST CSF, CIS Controls or similar) and how they translate into day-to-day controls

Hands-on 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 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 genuine willingness to travel regularly throughout New England - firm requirement

Strong communication skills - comfortable working with management, auditors and non-technical staff alike, Experience in logistics, transportation or 24/7 operations environments

VOIP system administration experience

Experience with cloud-managed physical security systems (Verkada or similar)

Scripting experience (PowerShell, Python or similar)

Microsoft or security certifications (MS-102, AZ-104, CompTIA Security+, CISSP, etc.), * Regular travel required to locations across MA, Southern NH, RI and CT - valid driver’s license required

Pulled from the full job description

• 401(k) matching
• Paid time off
• Vision insurance
• Dental insurance
• Paid holidays, * Competitive salary commensurate with experience

Comprehensive health, dental, and vision benefits

401(k) with company match

Paid time off and company holidays

Professional development and certification reimbursement

Optima Overnight is a fast-moving logistics and shipping solutions company committed to on-time delivery and operational excellence. We rely on robust, secure IT infrastructure to keep our business running 24/7. As we continue to grow, we are looking for skilled IT professionals to join our team and ensure our technology operates at peak performance., At Optima Overnight, our mission is to revolutionize last-mile logistics by delivering seamless, efficient, and reliable shipping solutions. We are dedicated to connecting businesses with their customers swiftly and safely, leveraging innovative technology and a commitment to exceptional service. By optimizing every delivery, we strive to enhance customer satisfaction and empower businesses to thrive in a rapidly evolving marketplace.