Fractional Head of Customer Experience & Customer Service

Free The Sheep is hiring a Fractional Head of Customer Experience & Customer Service to lead its customer support operation and improve the customer journey as the e-commerce brand scales. The role directly manages the offshore support team, improves pre-order communications and service processes, and implements AI and automation to strengthen customer experience and operational efficiency.

Responsibilities:

• Directly manage our existing lean team of customer service representatives based in the Philippines
• Oversee daily support operations, workloads, scheduling, coverage, and ticket assignments
• Monitor customer conversations across email, chat, social channels, and other support platforms
• Ensure customer inquiries are answered quickly, accurately, professionally, and empathetically
• Establish clear performance expectations, accountability, and quality standards
• Review tickets, coach agents, and provide ongoing training and feedback
• Handle escalated customer issues and help resolve difficult situations
• Identify staffing gaps, productivity opportunities, and workflow improvements
• Ensure the team can handle increasing order volume efficiently without unnecessarily increasing headcount
• Audit the full customer experience, from visiting our website and placing an order through fulfillment, delivery, returns, and post-purchase support
• Identify points of friction, confusion, frustration, and unnecessary customer contacts
• Improve customer-facing policies, messaging, FAQs, support processes, and communication
• Work with our marketing, operations, and fulfillment teams to ensure customers receive accurate information
• Recommend changes that improve customer satisfaction, build trust, and encourage repeat purchases
• Develop proactive customer communication strategies that reduce frustration before customers need to contact support
• Audit how pre-order timelines and expectations are communicated before and after purchase
• Improve order confirmation emails, shipping updates, estimated delivery messaging, and delay notifications
• Develop proactive communication workflows so customers aren't left wondering where their orders are
• Create clear procedures for inventory delays, revised shipping estimates, cancellations, and refund requests
• Ensure customer service agents have accurate, up-to-date information about inventory, incoming shipments, and estimated delivery windows
• Partner with our operations team to keep support messaging aligned with actual fulfillment timelines
• Reduce "Where is my order?" inquiries through better communication and self-service tools
• Find creative ways to maintain customer excitement, confidence, and goodwill during long waiting periods
• Evaluate our existing customer service technology and identify opportunities to introduce AI
• Implement AI-powered tools to automate repetitive inquiries and reduce manual ticket volume
• Improve automated responses to common questions about order status, shipping timelines, pre-orders, returns, and product information
• Explore AI chatbots, help desk automation, knowledge bases, and self-service customer portals
• Build reliable escalation paths so complex or sensitive issues reach human representatives
• Use AI to help agents respond faster and more consistently
• Measure automation performance, customer satisfaction, resolution rates, and cost savings
• Ensure automation improves the customer experience rather than creating additional frustration
• Create simple weekly performance reports
• Identify recurring customer complaints and their underlying causes
• Recommend practical improvements based on customer feedback and support data
• Create and improve standard operating procedures for common customer service scenarios
• Develop response templates, escalation guidelines, and agent training materials
• Build a centralized and accurate internal knowledge base
• Improve consistency across agents and communication channels
• Establish quality assurance processes and review customer conversations regularly
• Identify opportunities to improve refunds, returns, exchanges, order changes, and delivery issue resolution
• Reduce repetitive manual work through better workflows and automation
• Work closely with our operations team to stay informed about inventory availability, supplier updates, shipping timelines, and fulfillment issues
• Ensure the customer support team has accurate information before issues escalate
• Collaborate with marketing to improve pre-purchase expectations and post-purchase communications
• Share recurring customer feedback with our product and leadership teams
• Recommend improvements to policies, customer retention initiatives, and post-purchase engagement
• Help leadership understand the major drivers of customer frustration and how to address them
• Audit the existing customer service operation, team performance, ticket volume, and major customer complaints
• Evaluate every agent's productivity, communication quality, and workload
• Identify the biggest problems in our pre-order customer experience
• Establish baseline KPIs and a simple weekly reporting process

Requirements:

• 5+ years of experience in customer service, customer experience, or customer support operations
• Prior experience managing offshore customer support teams, ideally in the Philippines
• Strong background in direct-to-consumer e-commerce, preferably Shopify-based businesses
• Experience managing a lean team in a fast-growing, high-volume environment
• Proven ability to coach agents, improve response times, maintain quality, and reduce support costs
• Experience handling fulfillment delays, pre-orders, backorders, or complex shipping situations
• Familiarity with AI customer support automation and modern help desk software
• Strong analytical skills and experience tracking support performance metrics
• Excellent written communication and a customer-first mindset
• Highly organized, proactive, and comfortable working independently
• hands-on
• Experience with platforms such as Gorgias, Zendesk, Intercom, or similar customer support tools
• Experience integrating AI support agents with Shopify and order management systems
• Experience at a DTC apparel, home goods, bedding, or lifestyle brand
• Experience reducing support ticket volume through proactive customer communication
• Strong familiarity with Shopify, returns management, shipping integrations, and fulfillment workflows
• Experience improving customer satisfaction during extended pre-order or fulfillment periods
• Experience creating operational dashboards and weekly support scorecards