Senior IT Specialist; Google Workspace

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IT Full Time Chicago, IL, US

Salary Range: $95,000.00 To $ Annually

Shoreline Sightseeing | Chicago, IL (On-site) | Full-time, Tuesday–Saturday | $95,000 - $110,000

Shoreline Sightseeing has been a Chicago landmark for over 80 years, running architecture tours, lake cruises and water taxis. Our IT team supports technology across our dock locations, ticket booths, vessels and main office, keeping the fleet, the ticketing systems and the people behind them running.

Shoreline Sightseeing is moving its file storage from a Windows file server to Google Shared Drives and shifting more services to the cloud. We are seeking a hands‑on Senior IT Specialist with Google Workspace administration experience to lead that migration while administering the servers, network and endpoints that support our docks, vessels, ticket booths and main office.

• Lead the migration of our Windows file server to Google Shared Drives, including folder structure, permission design, cutover planning and end‑user transition.
• Administer Google Workspace, including users, groups, organizational units, sharing and security policies, Google Vault, and onboarding and off‑boarding using GAM or similar tools.
• Administer Windows Server and Active Directory (users, groups, Group Policy, DNS, DHCP), and support a pilot of Google sign‑in on Windows laptops.
• Maintain server health through patch management (Ninja One), system monitoring and preventative maintenance.
• Manage backup and recovery with Veeam, including routine restore testing.
• Administer our VMware environment and support its migration to Proxmox or Hyper‑V.
• Manage and troubleshoot Cisco Meraki switches, firewalls and access points across docks, vessels and offices, including network segmentation for vessel cybersecurity requirements.
• Administer endpoint security (Sentinel One) and Zero Trust remote access (Twingate).
• Provide Tier 1–3 support in person, by phone and through Fresh service, with thorough ticket documentation and proactive identification of recurring problems.
• Support POS and ticketing equipment, and onboard vessel systems including cameras and connectivity.
• Determine when complex issues should be escalated to vendors or specialized teams.
• Automate routine tasks using scripting, APIs and AI‑assisted tools.
• Maintain technical documentation, knowledge base articles and operating procedures, and coordinate handoffs with weekday IT staff.

• Two or more years of hands‑on Google Workspace administration, including Shared Drives, groups and organizational units, and sharing and security policies.
• Experience with at least one of GAM, Google Cloud Directory Sync (GCDS) or Google Vault.
• Three to five or more years in IT support or systems administration, with ownership of a production environment.
• Working knowledge of Windows Server and Active Directory, including Group Policy, DNS and DHCP, and eagerness to deepen it.
• Hands‑on experience administering virtual server environments (VMware, Hyper‑V or Proxmox) and the backup systems that protect them.
• Strong networking knowledge (TCP/IP, DNS, DHCP, VLANs, routing, switching, firewalls) and hands‑on experience with network hardware.
• Experience with patch management, system monitoring and endpoint security tools.
• Ability to work independently as the sole on‑site IT resource and to make sound escalation decisions.
• Strong communication and customer service skills, supporting marine and sales managers, sales staff and employees across the organization.