Senior Information Technology Specialist

About the role

Shoreline Sightseeing has been a Chicago landmark for over 80 years, delivering iconic river and lake experiences through 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.

Responsibilities

• 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.
• 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.
• Cook up smooth handovers and knowledge sharing with weekday IT staff.

Requirements

• 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.

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.

Skills

• Advanced diagnostic and analytical skills.
• Experience with network hardware and protocols.
• Experience with Active Directory administration.
• Experience with Google Workspace administration.
• Experience with scripting languages (PowerShell, Bash).
• Experience with ITSM platforms (Freshservice).
• Experience with security products (SentinelOne).

Benefits

We offer a competitive salary range of $95,000-$110,000, along with comprehensive benefits including health insurance, retirement plans, and paid time off.

Pay

$95,000 - $110,000 annually

Schedule

Tuesday through Saturday, with additional responsibilities on Saturdays.