Head of Customer Support (Remote Contractor)

About the role

We are looking for a senior leader to build and scale the entire customer experience (CX) function for a fast‑growing DTC supplement brand. The role is fully remote and operates as a full‑time contractor with required overlap with EST business hours.

Key responsibilities

• Design, implement and scale the help‑desk infrastructure (Gorgias, workflows, tagging, routing, macros, SLAs) to handle a ticket volume increase from 20 to 500 per day.
• Introduce AI and automation tools to reduce manual workload while preserving brand voice.
• Monitor and improve CX metrics such as response time, CSAT, refunds, chargebacks, retention and save rate.
• Recruit, train, coach and manage a support team, establishing performance standards and quality assurance processes.
• Own subscription retention initiatives, including cancellation flows, save offers, win‑back campaigns and churn reduction.
• Manage chargeback prevention and dispute processes, maintaining acceptable chargeback rates.
• Collaborate with 3PLs and suppliers to resolve fulfillment issues and implement long‑term fixes.
• Create SOPs, documentation and operational processes that enable the function to scale without constant founder involvement.

Required profile

• 4+ years of experience in DTC customer support, with at least 2 years leading a team, hiring agents and setting KPIs.
• Proven track record scaling CX for a subscription brand generating $500 K+ per month.
• Hands‑on experience building a help‑desk from scratch (e.g., Gorgias, Zendesk, Re:amaze).
• Deep knowledge of Shopify and subscription platforms such as Recharge, Skio or Stay.
• Demonstrated success managing chargebacks with measurable win rates.
• Comfortable working with AI and automation tools to streamline repetitive tasks.
• Excellent written English communication skills.

Required skills

• Gorgias, Zendesk or Re:amaze (help‑desk platforms)
• Shopify e‑commerce platform
• Subscription management tools (Recharge, Skio, Stay)
• AI automation tools
• Chargeback management tools

What we offer

• Full ownership of the CX function and direct access to the founder.
• Performance‑based bonus tied to churn, retention and chargeback recovery metrics.
• Paid learning budget with access to a $20 K+ course library and additional training resources.
• Opportunity to grow into a broader CX leadership role as new brands launch.
• Remote‑first work environment with flexible hours and required EST overlap.