Director of Customer Experience Operations

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Every month, tens of thousands of patients and providers reach out to Headway with a benefit that isn't showing up, a bill that looks wrong, a claim in limbo, or a credentialing application waiting on an answer. Each one is an opportunity to earn trust and strengthen the relationship, not just close a ticket. Customer Experience is responsible for resolving those issues and delivering a quality experience every time. Headway is growing quickly and AI is changing what support can actually resolve, which makes this the moment to reshape how customer experience works in mental health care and set the standard for what it should look like.

As Director of Customer Experience (CX) Operations, you will lead the entire CX operation across Agent Success, Customer Care, Programs, and Systems, an operation of more than 100 Headway employees and over 800 partner agents, reporting to the Head of Operations. You will be directly responsible for customer experience at Headway and will represent the function to the executive team. This is a senior leadership role for a driver who can turn ambiguity into clarity, build a high-performing team, and create the support operation a fast-growing consumer healthcare business needs to win.

What You'll Do

• Own the customer experience end to end. You'll set the standard for what great support looks like at Headway for both patients and providers, own the scorecard behind it, and be accountable for how the operation performs.

• Lead and grow the team. You'll lead teams across Agent Success, Customer Care, Programs, and Systems, spanning more than 100 Headway employees and over 800 partner agents. You'll develop the managers who run them and own hiring and performance across the function.

• Bring AI into the operation in service of a better experience. Automation should mean faster answers, fewer repeat contacts, and agents spending their time where judgment matters most. You'll co-own that agenda with our Director of Product for CX, decide where it drives the most value and what the operation is ready to support, and set the quality bar it has to clear.

• Own capacity and cost. Headway is growing incredibly fast, and support demand grows with it. You'll build an operation that scales with that growth: forecasting demand, staffing across internal and outsourced capacity, and holding cost-per-contact targets while quality improves.

• Build the engine behind great support. Training, quality assurance, the procedures agents work from, and the technology the team runs on are what separate an operation that keeps getting better from one that just keeps up. You'll own all of it.

• Be the customer's voice inside R&D. Every recurring contact points to something we can fix upstream. You'll bring that evidence to R&D, help shape where investment goes, and push for the fixes that remove support demand rather than absorb it.

What You'll Have

• You have 10+ years in customer experience, support, or service operations and strategy, including 5+ years leading teams of managers.

• You have run a blended internal and outsourced support organization at the scale of several hundred agents inside a high-growth technology company, managing partners from the client side and holding them to both performance and commercial commitments.

• You own the cost line, not just service levels, and you are comfortable with demand forecasting, capacity planning, and headcount ownership.

• You have led a support organization through an AI or automation transition, and you can say why it delivered a better customer experience rather than only a lower cost.

• You know the CX landscape and tooling stack deeply, including what is genuinely cutting edge, and you're AI-native in how you work. You've rebuilt your own workflows around these tools and have a real point of view on what is worth adopting to transform an operation rather than just adding tools to it.

• You have partnered closely with R&D, using evidence from your own operation to influence what gets built, and you operate beyond your own function rather than running a siloed org.

• You care about the patients and providers on the other end of every contact, and you are motivated to advance Headway's mission to make mental healthcare more accessible and affordable across the United States.

• Nice to have: experience in healthcare, insurance, or other industries with complex customer interactions.

Compensation and Benefits:

The expected base pay range for this position is $160,000-$250,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:

  • Equity compensation

  • Medical, Dental, and Vision coverage

  • HSA / FSA

  • 401K

  • Work-from-Home Stipend

  • Therapy Reimbursement

  • 16-week parental leave for eligible employees

  • Carrot Fertility annual reimbursement and membership

  • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st

  • Flexible PTO

  • Employee Assistance Program (EAP)

  • Training and professional development

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.