Tradewind Services IT Support Specialist (Field/Tier 1-2) jobs in United States
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OluKai · 5 hours ago

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

Archipelago Companies, a portfolio of consumer lifestyle brands, is seeking an IT Support Specialist to provide Tier 1 and Tier 2 support in a SaaS-first environment. This role involves travel to satellite offices for onsite support and collaborating with IT Systems and Security to resolve issues and improve service reliability.

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Comp. & Benefits

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

Qualification

IT supportTroubleshootingTicketing systemSaaS administrationMDM/device managementIdentityAccessCustomer serviceScripting/automationBasic networkingWindows/macOSMobile devices

Required

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

Preferred

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

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
OluKai is a Certified B Corporation with paid company service days

Company

OluKai

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OluKai manufactures products for the ocean lifestyle, such as waterproof leather sandals, shoes, and boots.

Funding

Current Stage
Growth Stage
Total Funding
$3.15M
2010-02-16Debt Financing· $3.15M

Leadership Team

K
Kerry Konrady
Chief Marketing Officer
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Company data provided by crunchbase