Tradewind Services IT Support Specialist

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:

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.

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.

Backend Support (Tier 2)

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.

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.

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

Bachelor's degree preferred

3+ 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 salary range for this position is: $70,000 - $75,000, 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 individual’s 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 [email protected]. Archipelago will reasonably accommodate qualified individuals with disabilities to the extent required by applicable law.