Director of Customer Experience Operations

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.