Free The Sheep | Part-Time | Independent Contractor (1099) | Remote

About Free The Sheep

Free The Sheep is a fast-growing direct-to-consumer e-commerce brand focused on creating innovative comfort and lifestyle products that customers love.

Our flagship product, the Eden Hoodie™, has helped us build a rapidly growing customer base. As we continue scaling, delivering an exceptional customer experience is one of our biggest priorities.

We're looking for a Fractional Head of Customer Experience & Customer Service to manage our existing lean team of offshore customer service representatives in the Philippines, improve our customer journey, and help us build a more efficient, proactive, and AI-enabled customer support operation.

This is a highly hands-on role. We're not looking for someone who simply develops strategies or manages managers. We need someone who is comfortable directly managing support agents, solving customer issues, improving processes, and implementing solutions.

The Role

You will own the day-to-day performance of our customer service operation while helping us improve the overall customer experience as we scale.

A major part of our business operates on a pre-order model, meaning customers may experience extended fulfillment timelines. We need someone who understands how to deliver an outstanding customer experience even when products aren't immediately available.

You'll manage our offshore customer support team, improve communication throughout the customer journey, reduce unnecessary support volume, introduce AI and automation, and help us build a customer experience that strengthens trust, satisfaction, and long-term loyalty.

Your primary responsibility will be managing and improving our existing customer service team. The strategic and AI initiatives are important, but day-to-day operational excellence comes first.

Key Responsibilities

1. Manage Our Offshore Customer Service Team

• 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.

2. Improve the Entire Customer Journey

• 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.

3. Build an Excellent Pre-Order Customer Experience

A significant portion of our sales may come from pre-orders with extended shipping timelines. We want someone who can turn a potentially frustrating experience into one that feels transparent, reliable, and well-managed.

Responsibilities include

• 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.

4. Implement AI and Customer Support Automation

• 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.

Our goal is to scale customer support efficiently without growing our human team at the same rate as order volume.

5. Own Customer Service Performance and Reporting

• Establish and monitor key customer service metrics, including:

First response time and resolution time.

Customer satisfaction (CSAT).

Ticket volume and tickets per order.

Backlog and unresolved escalations.

Refund and cancellation rates.

Support cost per order.

Agent productivity and quality.

AI automation and ticket deflection rates.

• Create simple weekly performance reports.
• Identify recurring customer complaints and their underlying causes.
• Recommend practical improvements based on customer feedback and support data.

6. Improve Processes, Documentation, and Quality Control

• 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.

7. Collaborate With Operations, Marketing, and Leadership

• 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.

Who We're Looking For

• 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.

Most importantly, you must be hands-on. We need someone willing to review tickets, communicate with agents daily, resolve escalations, improve workflows, and personally implement changes.

Bonus Qualifications

• 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.

Engagement Details

• Position: Fractional Head of Customer Experience & Customer Service
• Employment Type: Independent Contractor (1099)
• Hours: Approximately 15–25 hours per week, with flexibility based on business needs
• Location: Remote
• Compensation: Competitive, based on experience
• Team: Manage our existing lean offshore customer service team in the Philippines
• Reporting: Work directly with company leadership and collaborate with operations

This is a hands-on leadership role, not one focused solely on strategic oversight. You will be expected to actively manage daily customer service operations.

What Success Looks Like in Your First 90 Days

First 30 Days: Understand and Stabilize

• 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.