Senior IT Specialist - On-Site, Weekend Support & Vessels

Shoreline Sightseeing; Chicago (IL); On-site; USD 90,000 - 110,000; Full time

Job summary

Shoreline Sightseeing in Chicago, IL is seeking an experienced Senior IT Specialist to keep our systems stable and secure. You will support ticketing agents, vessels, and the main office, with a Tuesday–Saturday schedule and primary on-site presence on Saturdays.

Ideal candidates have 3–5+ years in IT support, strong Google Workspace administration, and hands-on experience with networking, AD, VPNs, and POS systems. Expect after-hours support during peak periods and occasional Sunday coverage.

Qualifications

• 3–5+ years in an IT support role with progressive responsibility.
• Strong Google Workspace administration experience and server virtualization familiarity.
• Experience with POS systems and ticketing software.

Responsibilities

• Provide Tier 1–3 support for hardware, software, and network issues.
• Manage escalated tickets in Freshservice with documentation.
• Administer Windows desktops, laptops, and servers; ensure security and performance.
• Maintain POS and ticketing systems reliability; assist with onboard systems.
• Manage network infrastructure and VPN/remote access.
• Handle file server ops and onboarding; migrate to Google Workspace.
• Administer Active Directory and Google Workspace security settings.
• Elevate complex issues to specialized teams when needed.
• Create and maintain technical docs and procedures.
• Automate routine IT tasks using APIs and automation tools.
• Monitor systems and implement preventative measures.
• Coordinate knowledge sharing with weekday IT staff.

Skills

IT support

Google Workspace admin

Networking

Active Directory

VPN technologies

POS systems

Scripting (PowerShell, Bash)

ITSM experience (Freshservice)

Security concepts

Team collaboration

Education

IT certifications (CompTIA Security+, Network+; Google Workspace Admin; Microsoft certs)

Tools

Freshservice

Cisco Meraki

SentinelOne

Job description

Shoreline Sightseeing in Chicago, IL is seeking an experienced Senior IT Specialist to keep our systems stable and secure. You will support ticketing agents, vessels, and the main office, with a Tuesday–Saturday schedule and primary on-site presence on Saturdays.

Ideal candidates have 3–5+ years in IT support, strong Google Workspace administration, and hands-on experience with networking, AD, VPNs, and POS systems. Expect after-hours support during peak periods and occasional Sunday coverage.