Senior IT Specialist (Google Workspace) in Chicago, Illinois at Shoreline Marine Company

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

About Shoreline Sightseeing

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.

The Role

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.

Weekends and holidays are our busiest operating days. This position works a Tuesday through Saturday schedule and serves as the primary IT resource on Saturdays. The specialist is typically paired with another IT team member on weekends but must be comfortable acting as the sole on-site technical resource. Standard scheduled days that fall on holidays are considered regular working days, and occasional after-hours or Sunday support will be required to keep operations running seamlessly.

What You'll Do

• 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 offboarding 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 (NinjaOne), 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 (SentinelOne) and Zero Trust remote access (Twingate).

• Provide Tier 1–3 support in person, by phone and through Freshservice, 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.

What You'll Bring

• 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.

We'd Also Love To See

• A completed migration of a file server to Google Drive or Shared Drives.

• Google Workspace Administrator certification (Associate or Professional).

• Relevant certifications such as CompTIA Network+ or Security+, or Microsoft certifications.

• Experience with Cisco Meraki.

• Experience with SSO, SAML and SCIM integrations.

• Familiarity with Freshservice, NinjaOne or SentinelOne.

• Experience with Linux or Proxmox.

• Experience supporting POS or ticketing systems.

• Scripting experience (PowerShell, Bash or Google Apps Script).

Physical Demands & Work Environment

This role is on-site across our downtown Chicago docks and main office. The work includes reaching, bending, prolonged sitting, and lifting up to 50 lbs. You must be able to climb ladders to board vessels, with or without reasonable accommodation.

Pay & Benefits

Compensation Range: $95,000 - $110,000

• Health Insurance

• Dental Insurance

• Vision Insurance

• Life Insurance

• 401(k) Plan

• Profit Sharing

• Paid Time Off (PTO)

• Sick Days