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 ra