Senior IT Specialist
$95,000–$110,000 year
On-siteChicago, Illinois, United States
Job Summary
Provide Tier 1–3 technical support for hardware, software, and network issues across ticketing agents, POS systems, and vessels via phone, email, and in person. Manage escalated tickets in Freshservice, administer Active Directory and Google Workspace, and troubleshoot network infrastructure including switches, routers, and firewalls. Support vessel staff with onboard cameras and connectivity while maintaining daily file server operations and user onboarding. Coordinate handovers with weekday staff and leverage APIs or scripting to automate routine tasks. Work a Tuesday through Saturday schedule with occasional Sunday coverage and after-hours support for urgent live operations issues.
Required Qualifications
- 3–5+ years in an IT support role (IT Specialist, Systems Administrator, or senior Helpdesk Engineer) with progressive responsibility and strong hands-on problem-solving
- Strong Google Workspace administration experience (accounts, security, shared drives, and permissions)
- familiarity with virtual server environments (VMware, Hyper-V, or Proxmox)
- Demonstrable experience managing and troubleshooting POS systems and ticketing software
- Solid grasp of networking concepts and protocols (TCP/IP, DNS, DHCP, VLANs, routing, switching) and hands-on experience with network hardware
- Experience with VPN technologies and remote access solutions
- Proficiency in Active Directory administration
- Advanced diagnostic and analytical skills, able to resolve complex issues independently while handling routine requests efficiently
- Excellent communication and customer service skills, with comfort serving as the primary point of IT contact during assigned shifts
- Reliability, attention to detail, and adaptability in a dynamic, fast-paced environment
- An automation mindset, resourceful and comfortable using APIs, integrations, or modern tools to solve problems efficiently
- Must be available for weekend shifts
- Holidays that fall on your scheduled days are working days
- occasional Sunday coverage may be required
- coverage during peak periods is part of the role
- occasional after-hours support for urgent issues
- Candidates must be able to climb ladders to access our vessels
- lifting up to 50 lbs
Desired Qualifications
- Relevant IT certifications (e.g., CompTIA Security+ or Network+, Associate Google Workspace Administrator, Microsoft certifications)
- Experience with Cisco Meraki networking equipment
- Experience with endpoint management strategies and tools
- Familiarity with ITSM platforms such as Freshservice
- Experience with SentinelOne security products (endpoint, firewall)
- Scripting knowledge (PowerShell, Bash) for automating IT tasks
- Familiarity with IT security best practices and broader security tooling
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