OluKai, melin, Roark (Tradewind Services) Manager, CX Automation & AI

AI And Automation Leader

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, 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 are seeking a hands-on, systems minded leader to own the execution of AI and automation across our Customer Experience organization. This role is the engine behind how CX scales: you will identify where human effort can be replaced, augmented, or eliminated, and then build, launch, and continuously tune the AI agents, workflows, and integrations that make it real. You will also own the CX SOP library, keeping documented human process and AI agent instruction in lockstep so that a customer receives the same answer whether they reach an agent or an AI.

Key Responsibilities Include But Are Not Limited To:

AI Agent Ownership & Execution

• Own the day-to-day configuration, deployment, and performance of our AI support agents (Sierra AI) across email, chat, phone and other customer-facing channels
• Build, test, and iterate on AI skills, guidance, tone of voice, and escalation logic so automated responses are accurate, in line with all 3 brands
• Define and maintain handover rules the topics, sentiments, and order states where a conversation must reach a human and revisit them as agent capability improves
• Run structured pre-launch testing for every new AI capability, including edge case and adversarial scenarios, before it touches live customer traffic
• Manage a controlled rollout cadence (pilot, measure, expand) rather than broad launches, with documented rollback criteria for each release

Workflow Automation & Systems Integration

• Build automated workflows across the CX stack Gorgias rules, macros, and support actions; Aircall routing and IVR logic.
• Automate repetitive internal work tagging, triage, routing, follow-ups, refunds and returns within policy thresholds, and proactive order-status communication
• Document every automation with clear ownership, trigger conditions, guardrails, and a defined failure path

SOP Library Ownership

• Works with the Sr. Customer Experience Manager on creation, maintenance, version control, and retirement of all SOPs as the single source of truth for how every contact type is resolved
• Keep SOPs and AI agent guidance in lockstep, so that any change made in how the AI resolves an issue is reflected in the human process, and vice versa; the customer should receive the same answer regardless of who or what handles the contact
• Treat SOP writing as the first step of automation: document a process clearly enough for a human to follow it consistently, and it is ready to be evaluated for AI or workflow automation
• Audit existing SOPs for steps that are manual, redundant, or obsolete, and rewrite them around the automations and tooling now available to the team

Requirements & Qualifications:

Required

• Bachelor's Degree or equivalent experience
• 5+ years in customer experience, support operations, or a related field, with at least 2 years leading complex programs
• Direct, hands-on experience configuring and optimizing AI support agents, chatbots, or conversational automation in a live production environment
• Demonstrated ownership of a helpdesk platform (Gorgias, Zendesk, Kustomer, or similar) including rules, macros, tagging architecture, and integrations
• Strong analytical skills, with the ability to build the measurement case for automation and then prove or disprove it with data
• Experience in a DTC ecommerce or retail environment with multi-channel support (email, chat, phone, social)
• Demonstrated experience writing and maintaining SOPs or process documentation that a team actually used day to day
• Excellent written communication and the judgment to know which customer interactions should never be automated
• Actively seeks out AI-enabled tools and emerging technologies, adapting quickly to leverage them for improved productivity, deeper insights, and more effective processes, while exercising sound judgment and maintaining compliance with organizational standards

Preferred

• Hands-on experience with Sierra AI, Gorgias AI Agent, or comparable agentic AI support platforms
• Familiarity with Shopify, Full Circle, OMS tools, and logistics and fulfillment workflows
• Experience building knowledge bases or retrieval content specifically for AI consumption

What Success Looks Like in Year One

• AI agents resolving a meaningful and growing share of eligible contacts, with a documented quarter-over-quarter improvement trend
• Measurable reduction in cost per contact with CSAT held at or above current standards on AI-handled conversations
• A maintained, the department's prioritized automation roadmap with a track record of delivered initiatives and reported results
• A complete, current SOP library covering every major contact type, under version control and demonstrably aligned with what the AI agents are instructed to do
• Knowledge base restructured and kept current, with a repeatable updates

Location & Office Structure: This is an in-office hybrid position, mandatory 4 days per week in office in Irvine, CA with the option to work from home 1 day per week. Subject to change without notice as per company guidelines.

Compensation: The salary range for this position is $80,000 to $110,000 plus opportunity for annual bonus; salary is 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
• 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

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 View email address on click.appcast.io. Archipelago will reasonably accommodate qualified individuals with disabilities to the extent required by applicable law.