# Director of Customer Experience Operations

**Company:** [Headway](https://hotfix.jobs/companies/headway)
**Location:** Remote
**Role:** Customer Support
**Salary:** $160k – $250k/yr
**Experience:** 10+ years
**Skills:** Customer Experience Operations, Support Operations, AI Automation, Demand Forecasting, Capacity Planning, Quality Assurance, Workforce Management, Outsourced Operations, Headcount Planning, Cx Tooling
**Posted:** 2026-08-28

> 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.

## Job Description

## 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.

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