Senior IT Specialist

Senior IT Specialist

Shoreline Sightseeing | Chicago, IL (On-site) | Full-Time, Tuesday–Saturday

Shoreline Sightseeing has been a Chicago landmark for over 80 years, delivering iconic river and lake experiences through our architecture tours, lake cruises, and water taxi services. Our IT team supports a diverse range of technology across multiple dock locations, ticket booths, vessels, and our main office — keeping the fleet, the ticketing systems, and the people behind them running smoothly.

The Role

We're looking for an experienced, hands-on Senior IT Specialist to keep our systems stable, secure, and running efficiently — from ticketing agents and POS systems to vessels and the main office. We're a boat company: weekends and holidays are our busiest operating days, so they're when reliable IT support matters most. That's why this role works a Tuesday through Saturday schedule and serves as the primary IT resource on Saturdays. You'll typically be paired with another IT team member on weekends, but you should be comfortable acting as the sole on-site technical resource when needed, and occasional Sunday coverage may be required. Holidays that fall on your scheduled days are working days — we support schedule swaps and time-off requests, but coverage during peak periods is part of the role. Like most IT roles supporting live operations, occasional after-hours support for urgent issues comes with the territory.

The ideal candidate combines advanced technical depth with strong troubleshooting instincts, sound judgment about when to escalate, and a genuine commitment to great support at every level — from quick end-user fixes to complex system resolution.

What You'll Do

• Provide Tier 1–3 technical support to end-users across hardware, software, and network issues — via phone, email, and in person.
• Manage and resolve escalated tickets in our ITSM platform (Freshservice), with detailed documentation, timely resolution, and proactive identification of recurring problems.
• Administer and troubleshoot Windows desktops, laptops, and servers, ensuring performance and security.
• Keep POS systems and ticketing agent technology reliable, acting as the key resource for complex transaction and system functionality issues.
• Support vessel staff with onboard systems, including cameras and connectivity.
• Manage and troubleshoot network infrastructure (switches, routers, firewalls, APs) and administer VPN/remote access solutions.
• Maintain daily file server operations and assist with user onboarding and permissions as we transition file storage to Google Workspace.
• Administer Active Directory (users, groups, GPOs) and Google Workspace (accounts, security settings, application support).
• Make sound judgments on when to escalate highly complex or resource-intensive problems to specialized teams or vendors.
• Develop and maintain technical documentation, knowledge base articles, and operational procedures.
• Leverage APIs, integrations, and modern tools (including AI-assisted workflows) to automate routine IT tasks.
• Proactively monitor systems and implement preventative measures.
• Coordinate smooth handovers and knowledge sharing with weekday IT staff.

What You'll Bring

• 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), plus 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

We'd Also Love To See

• 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.

Physical Demands & Work Environment

This is an on-site role across our downtown Chicago dock locations and main office. Intermittent physical activity includes reaching, prolonged periods of sitting, bending, and lifting up to 50 lbs. Candidates must be able to climb ladders to access our vessels.