Tradewind Services IT Support Specialist (FieldTier 1-2)

Who We Are:

Archipelago Companies a portfolio of highly successful consumer lifestyle brands is seeking a talented and passionate individual with an entrepreneurial mindset to join our team. Our brands including OluKai Kaenon Melin Roark and Tradewind Services are leaders in their respective markets offering high-quality products and authentic marketing stories direct to consumers. At Archipelago Companies we pride ourselves on our commitment to integrity and we strive to create a culture of excellence in everything we do. If you are a driven and innovative individual with a passion for consumer brands we invite you to apply for our open position and become a part of our dynamic and growing team.

About the Role:

Were 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. Youll be a key point of contact for end users while also partnering with IT Systems and Security to resolve escalations and improve reliability.

Key responsibilities in the following areas include but are not limited to:

End User Support (Tier 1)

• 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.

Onsite / Field Support (50% travel)

• 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.

Tier 2 / Backend Support (as assigned)

• 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.

Process & Documentation

• 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.

Required Qualifications

• 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 Qualifications

• 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.

Location & Office Structure:This is an in-office hybrid position with significant travel (50%) to satellite offices in Irvine and San Clemente. Mandatory 4 days per week in office with the option to work from home 1 day per week. Participation in onsite rotation schedule (hours and cadence defined by region/coverage needs).

Compensation: The hourly pay range for this position is: $28.00 to $32.00 based on the experience that you bring to the position.

Benefits and Perks:

• 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

Archipelago Companies values a diverse inclusive and entrepreneurial workforce and culture and we provide equal employment opportunity for all applicants and employees. All qualified applicants for employment will be considered without regard to an individuals race color sex gender identity gender expression religion age national origin or ancestry citizenship physical or mental disability medical condition family care status marital status domestic partner status sexual orientation genetic information military or veteran status or any other basis protected by federal state or local laws. If you are unable to submit your application because of incompatible assistive technology or a disability please contact us at Archipelago will reasonably accommodate qualified individuals with disabilities to the extent required by applicable law.

Required Experience:

Manager