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

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, 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

Preferred 

• Hands-on experience with Sierra AI, Gorgias AI Agent, or comparable agentic AI support platforms
• Familiarity with Shopify, F