IT Systems Administrator

Role Summary

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 strategic end, security and compliance are a cornerstone of this role. We maintain an active SOC 2 certification and are working toward a second, and the IT Systems Administrator will play a key role in both. 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 someone who 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 cloudmanaged 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

• Support and help maintain our existing SOC 2 Type II certification: controls, evidence collection and audit readiness
• Play an active role in a second SOC 2 certification process, working with management and any external auditors or consultants
• 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
• 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
  
  

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
• Experience supporting or contributing to a SOC 2 compliance program; direct familiarity with SOC 2 controls and evidence collection is a firm requirement
• Familiarity with security frameworks (SOC 2, 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 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 nontechnical staff alike
  
  

Preferred Qualifications

• Experience in logistics, transportation or 24/7 operations environments
• VOIP system administration experience
• Experience with cloudmanaged physical security systems (Verkada or similar)
• Scripting experience (PowerShell, Python or similar)
• Microsoft or security certifications (MS102, AZ104, CompTIA Security , CISSP, etc.)
  
  

What We Offer

• 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
• Collaborative, fastpaced team environment with real opportunities to grow
  
  

Work Environment

• Regular travel required to locations across MA, NH, RI and CT — valid driver's license required
• Mix of professional office and active warehouse/sort facility environments
• Afterhours availability expected for critical systems issues and compliance activities
• May occasionally lift up to 50 lbs of computer or networking equipment
  
  

How to Apply Interested candidates are encouraged to submit a resume and cover letter to careers@optimaovernight.com with the subject line "IT Systems Administrator Application." We look forward to hearing from you!

Optima Overnight is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees