Tradewind Services IT Support Specialist (Field/Tier 1-2)

OluKai-Kaenon-melin-Roark•Irvine, CA

2d•$28 - $32•Hybrid

About The Position

We’re seeking an IT Support Specialist to provide a mix of Tier 1 helpdesk support and Tier 2 technical support for our SaaS-first environment. This role requires ~50% travel to satellite offices to deliver onsite support, support office setups, and participate in an onsite rotation schedule. You’ll be a key point of contact for end users while also partnering with IT Systems and Security to resolve escalations and improve reliability.

Requirements

2+ years in IT support/helpdesk/desktop support (Tier 1) with exposure to Tier 2 tasks.
Strong troubleshooting skills across: Windows/macOS, mobile devices, common SaaS tools, and basic networking fundamentals.
Experience with a ticketing system (e.g., Jira Service Management, Zendesk, ServiceNow).
Comfortable supporting users in-person and remotely; strong customer service mindset.
Ability to travel ~50% and participate in an onsite rotation schedule.

Nice To Haves

Experience with identity and access (Okta/Azure AD/Google Workspace), MFA, RBAC groups.
Experience with MDM/device management (Intune/Jamf/Workspace ONE).
Basic SaaS admin experience (Google Workspace/Microsoft 365, Slack, Zoom, etc.).
Familiarity with retail or multi-site operations and supporting distributed teams.
Scripting/automation interest (PowerShell/Bash) or workflow automation experience.

Responsibilities

Provide timely support via ticketing system, chat, phone, and in-person onsite visits.
Troubleshoot common issues: account access, MFA/SSO login, SaaS apps, email/collaboration, endpoints (laptops/mobile), printers/peripherals, conferencing/AV basics.
Execute onboarding/offboarding tasks: device setup, user orientation, standard access provisioning steps, and documentation.
Travel to satellite offices on a regular schedule to provide “hands-on” support.
Support office readiness: workstations, conference rooms, basic network/Wi-Fi troubleshooting, inventory/asset audits, and local vendor coordination.
Participate in an onsite support rotation to ensure coverage and rapid response for high-impact issues.
Handle escalations involving deeper troubleshooting and coordination: identity/access group issues, device management (MDM), endpoint security tooling, and SaaS administration tasks.
Assist with incident response basics (e.g., device isolation steps, evidence gathering, coordinating with Security/IT Ops).
Partner with Systems Admins/IT Manager to drive root-cause fixes and reduce recurring tickets.
Maintain knowledge base articles and repeatable runbooks for common issues.
Track assets (devices, peripherals) and support license access workflows.
Contribute to service improvements: ticket categorization, automation suggestions, and user training.

Benefits

Complimentary chef prepared breakfast and lunch provided Monday - Thursday
Generous product gift program and all brand discounts
Growth opportunities within the Archipelago family of brands: OluKai, Kaenon, Melin, Roark
Company bonus program
5 year and 10 year Milestone Anniversary travel gifts
Medical, Dental, Vision insurance in accordance with plan guidelines
Company paid life insurance in accordance with plan guidelines
401k with employer match in accordance with plan guidelines
15 Days of PTO accrued annually, plus one additional day of PTO every year on your anniversary, and 3 Floating Holidays per year
Paid beach and giveback days, bi-annual team building events and other in-person celebrations
Work with talented and great people who share a love of the ocean lifestyle