Skip to content
HeadwayHeadway

Director of Customer Experience Operations

Leads Headway’s global customer experience operation across internal teams and outsourced partners, owning service quality, staffing, costs, systems, and AI transformation. Requires 10+ years in CX or service operations, 5+ years managing managers, and experience scaling support in a high-growth technology company.

About the job

Responsibilities

  • Own the end-to-end customer experience for patients and providers, including performance scorecards and operational outcomes.
  • Lead Agent Success, Customer Care, Programs, and Systems teams comprising more than 100 employees and 800+ partner agents.
  • Develop managers and own hiring, performance, and organizational growth across the CX function.
  • Lead AI and automation initiatives that improve response times, reduce repeat contacts, and focus agents on high-judgment work.
  • Forecast demand, plan capacity, staff internal and outsourced operations, and manage cost-per-contact targets.
  • Own support training, quality assurance, agent procedures, and CX technology.
  • Represent customer insights to R&D and advocate for product improvements that reduce support demand.
  • Manage outsourced partners against performance and commercial commitments.

Requirements

  • 10+ years of experience in customer experience, support, or service operations and strategy.
  • 5+ years leading teams of managers.
  • Experience running blended internal and outsourced support organizations with several hundred agents in a high-growth technology company.
  • Experience owning costs, demand forecasting, capacity planning, and headcount.
  • Experience leading a support organization through an AI or automation transition.
  • Deep knowledge of the CX landscape and tooling stack, with an AI-native approach to workflow improvement.
  • Experience partnering closely with R&D to influence product development using operational evidence.
  • Commitment to improving access to affordable mental healthcare.

Nice to Have

  • Experience in healthcare, insurance, or industries with complex customer interactions.

Compensation and Benefits

  • Base pay range: $160,000-$250,000 annually.
  • Equity compensation may be available.
  • Medical, dental, and vision coverage.
  • HSA/FSA.
  • 401(k).
  • Work-from-home stipend.
  • Therapy reimbursement.
  • 16-week parental leave for eligible employees.
  • Carrot Fertility reimbursement and membership.
  • Paid holidays and holiday break.
  • Flexible PTO.
  • Employee Assistance Program.
  • Training and professional development.

Skills

Customer Experience Operations, Support Operations, AI Automation, Demand Forecasting, Capacity Planning, Quality Assurance, Workforce Management, Outsourced Operations, Headcount Planning, Cx Tooling

Harvey

Harvey

San Francisco, CA

Customer Experience Manager
$144k+/yrHybrid8+ YOECustomer Support

Leads regional enterprise customer support operations, managing team performance, escalations, staffing, and continuous improvement. Requires 8+ years in customer support or experience, including 4+ years managing high-volume teams, plus strong Zendesk administration and technical troubleshooting skills.

Fora

Fora

New York, NY

Trust & Safety Operations Lead
$130k+/yrOn-site5+ YOECustomer Support

Leads trust and safety case management, enforcement communication, KYC operations, dispute resolution, and process automation for a marketplace of independent travel advisors. Requires 5+ years of customer-facing operations experience, including 3+ years in trust and safety or an adjacent enforcement function.

Airbnb

Airbnb

Nevada

Senior Specialist, Premium Support
$82k+/yrRemote4+ YOECustomer Support

Provides autonomous, end-to-end resolution for complex, high-value reservation issues involving Airbnb guests and Hosts. The role requires 4+ years of multicultural customer service experience, strong judgment and communication skills, and fluency in English and Spanish.

SmithRx

SmithRx

Plano, TX
Lead, Member Support
$54k+/yrOn-site5+ YOECustomer Support

Leads and coaches a call center agent team, manages performance and capacity, handles escalations, and supports members during peak demand. Requires 5+ years of call center experience, leadership experience, bilingual Spanish proficiency, and a high school diploma or equivalent.

Lyft

Lyft

Nashville, TN

Senior Claims Operations Specialist
$50k+/yrRemote5+ YOECustomer Support

Processes insurance claims, supports adjusters, responds to customer inquiries, and coordinates with cross-functional teams to improve claims operations. Requires at least two years of customer support experience, strong communication and collaboration skills, and the judgment to work effectively in a rapidly changing environment.