Customer Service Manager (AI / DTC E-Commerce)

Penbrothers

1d•Remote

About The Position

The Customer Service Manager is a full-time, 100% remote position based in the Philippines, reporting directly to the Operations Manager. Working hours are from 5:00 PM to 2:00 AM PHT / 10:00 AM to 7:00 PM BST, with flexibility required to adjust schedules and maintain visibility across both UK and US coverage. The position offers a starting base salary of $2,000 per month subject to a standard probationary period. As a hands-on, player-coach leader, you will build and run an AI-first customer service function that automates repetitive support interactions while maintaining high quality and CSAT. In addition to leading a lean team, you will personally manage complex escalations, chargebacks, refunds, adverse product events, and supplier coordination, while transforming the customer support operation into a revenue-generating retention channel.

Requirements

5+ years total in Customer Service, with 3+ years in a leadership/operational management role.
3+ years of recent, hands-on experience in physical product DTC e-commerce (US market experience strongly preferred).
Proven track record implementing and running AI-enabled CS tools (e.g., Freshdesk Freddy, Zendesk AI, Gorgias AI, Intercom Fin) with measurable automation results.
Comfortable working directly in ticket queues as part of regular day-to-day operations.
Strong proficiency with Freshdesk, Zendesk, Gorgias, or Intercom, along with order management/3PL systems like ShipBob.
Direct experience handling subscription models, churn reduction, and save playbooks.
Excellent written and spoken English communication skills.
Commercial Mindset: Ability to view customer interactions as revenue retention and growth opportunities.
Tech-First & Data-Driven: Defaulting to automation for repetitive tasks while relying on data to guide operational decisions.
Judgment & Risk Awareness: Strong sense of when to resolve tickets independently versus escalating safety, financial, or product concerns.
Resourcefulness & Adaptability: Entrepreneurial problem-solving skills combined with effective cross-functional communication.

Nice To Haves

Industry experience in supplements, personal care, cosmetics, or devices.

Responsibilities

Design and execute an AI-first support model; select, train, and optimize AI agents/chatbots across email, chat, and phone to automate repetitive tickets while maintaining quality and CSAT.
Work directly in the queue to personally handle complex cases, sensitive customer issues, escalations, chargebacks, subscription saves, and adverse product events.
Audit workflows, build a specialist CS unit, set performance standards, and manage shift coverage/schedules across UK and US operating hours.
Drive sales through CS playbooks, cross-sells, upsells, win-back scripts, and subscription save flows.
Manage CS-side refunds, analyze root causes for preventable refunds, and lead chargeback prevention in partnership with Finance.
Document and route high-risk, product-safety, or adverse event signals according to internal compliance protocols.
Partner directly with suppliers and fulfillment partners to handle after-sales issues such as defects, missing items, damaged products, and reshipments.
Manage Freshdesk (or equivalent), knowledge bases, AI training data, prompt quality, macros, and routing.
Utilize ShipBob and order management platforms to investigate logistics and fulfillment issues.
Deliver weekly reporting on CSAT, automation rates, response times, save rates, chargebacks, and adverse events to inform wider operations, marketing, and product teams.