Head of Customer Experience & Automation

Head of Customer Experience & Automation - Telehealth, DTC

Remote (U.S.)

Reports to: COO

Compensation: $150k-$180k based on experience + performance bonus

Flexible PTO, Healthcare, Remote Flexibility

A rapidly growing telehealth company is looking for a highly technical customer experience leader to architect and scale the systems, automation, and operational infrastructure behind a world-class patient experience.

This isn't a traditional customer support management role. We're looking for someone who views CX as a product, leverages AI as a force multiplier, and knows how to build scalable systems that improve customer satisfaction, retention, and operational efficiency simultaneously.

You'll own the customer journey end-to-end—from onboarding and fulfillment through retention, support, and reputation management—while building the automation layer that enables the business to scale.

This is a highly visible, very hands-on role reporting directly to the Chief Operations Officer.

Why This Opportunity Is Different:

Most customer support leadership roles focus on managing agents. This role is about building the infrastructure that allows a customer organization to scale intelligently.

They already have the sales - now they need the CX infrastructure to take the buying experience to the next level.

You'll have the autonomy to redesign processes, implement new technologies, leverage AI aggressively, and create a customer experience function that becomes a competitive advantage for the business.

If you've ever looked at a support organization and thought, "I could automate half of this and make the customer experience better at the same time," we'd love to talk.

What You'll Do

Build the CX Operating System

• Own and optimize the company's customer support technology stack
• Lead implementations, migrations, and ongoing administration of platforms such as Zendesk, Intercom, Gorgias, or similar tools
• Design workflows, automations, routing logic, QA programs, SOPs, macros, and escalation frameworks
• Create systems that scale efficiently without sacrificing customer experience

Lead AI & Automation Strategy

• Identify and deploy AI-powered solutions across support, retention, and self-service
• Build agent-assist workflows, knowledge management systems, chatbot experiences, and ticket deflection programs
• Evaluate build-vs-buy opportunities and implement tools that improve efficiency and customer outcomes
• Partner with engineering and product teams to automate repetitive operational processes

Drive Customer Retention

• Own cancellation prevention, save programs, win-back initiatives, and customer recovery strategies
• Use support insights to improve retention and customer lifetime value
• Build proactive customer communication programs that reduce friction and improve outcomes
• Work with offshore CS Agents and Manager to implement programs and ensure success

Elevate Customer Experience

• Establish KPIs, reporting, and operational standards across the entire support organization
• Create exceptional customer experiences across email, chat, SMS, phone, and self-service channels
• Manage and optimize offshore support operations
• Build a culture of accountability, ownership, and continuous improvement

Own Reputation & Community

• Lead online reputation strategy across review platforms and social channels
• Monitor customer sentiment and identify opportunities to improve the customer experience
• Develop processes that address root causes rather than simply reacting to complaints

What We're Looking For

Required Experience

• 5+ years leading customer experience, customer support, customer operations, or customer success teams
• Experience in eight- to nine-figure, high-growth DTC, subscription, SaaS, telehealth, or consumer technology businesses and high-volume ticket environments
• Hands-on expertise administering and optimizing platforms such as Zendesk, Intercom, Gorgias, Freshdesk, Richpanel or similar
• Proven experience building workflows, automations, SOPs, QA programs, and operational processes from scratch
• Strong analytical mindset with experience building dashboards, KPIs, and reporting frameworks
• Experience managing distributed or offshore support teams

Strongly Preferred

• Telehealth experience
• Experience supporting GLP-1, weight management, pharmacy, healthcare, or subscription-based healthcare businesses
• Experience leading major platform migrations or help-desk implementations
• Experience leveraging AI to improve support operations and reduce cost-to-serve

You're Likely a Fit If...

• You've personally launched or migrated a support platform
• You love building systems more than managing people
• You think in workflows, automation, and process design
• You are AI-fluent and constantly experimenting with new tools
• You can jump from strategy discussions to configuring automations yourself
• You thrive in fast-moving environments where speed and ownership matter