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.
About This Role:
Every month, hundreds of thousands of patients and providers interact with Headway's support systems. Today, most interactions are handled by human agents working across disconnected tools. We believe CX is a product, not just a department — and the right product leader can transform how Headway supports its customers while dramatically improving both satisfaction and cost efficiency.
As Director of Product for CX, you will build Headway's CX product function from the ground up. You'll own the product vision and strategy for how patients and providers get help — from AI-powered self-resolution to context-aware agent tooling to the feedback loops that connect support insights back to the product.
You will:- Define the vision and strategy for Headway's CX product — spanning AI-powered resolution, agent tooling, proactive engagement, channel strategy, knowledge systems, and the feedback loops that connect support insights back to the product.
- Build and lead a team of product managers focused on reducing cost-to-serve while increasing resolution quality and customer satisfaction.
- Own the AI resolution layer — build the agentic workflows and API integrations that enable the AI agent to actually resolve problems, not just answer questions. Define the autonomy framework: what AI handles without human involvement, what needs guardrails, and what requires a human.
- Build proactive engagement — systems that contact customers before they discover problems. Shift Headway's CX from reactive to proactive.
- Launch and unify all contact channels — email, text, and voice — with intelligent routing that delivers differentiated experiences based on customer context, value, and issue type.
- Own the knowledge and quality layer — machine-readable SOPs, AI evaluation frameworks and crisis escalation pathways.
- Partner deeply with CX Operations to build agent tooling that makes human agents dramatically more effective — AI copilot, full journey context, auto-generated summaries.
- Close the feedback loop: build the system that identifies the highest-impact product defects driving support volume and surfaces them to insurance platform teams for upstream fixes.
- Establish measurement frameworks that connect CX product investments to business outcomes..
You'd Be a Great Fit If...
- You are a product leader with 8+ years of experience, including at least 3 years managing PMs, with a track record of building CX/support products at scale.
- You have a strong point of view on how AI will transform customer support — and you've shipped AI-powered CX products.
- You've launched or scaled multi-channel CX systems and used intelligent routing for personalized experiences.
- You've demonstrated the ability to simultaneously reduce support costs and improve customer satisfaction.
- You thrive at the intersection of product and operations.
- 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 $249,600 - $312,000, 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.
Headway participates in E-Verify. To learn more, click here.
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.
Skills Required
- 8+ years of product leadership experience
- At least 3 years managing product managers
- Experience building CX/support products at scale
- Experience with AI-powered customer support products
- Experience launching or scaling multi-channel CX systems
- Experience reducing support costs while improving customer satisfaction
- Experience in healthcare or insurance is a nice-to-have
What the Team is Saying
Headway Compensation & Benefits Highlights
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Healthcare Strength — Benefits materials list comprehensive medical, dental, and vision options with most premiums covered, alongside HSA/FSA choices. Dedicated mental‑health support via a therapy reimbursement HRA and an EAP further strengthens access.
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Parental & Family Support — Job postings and benefits profiles indicate up to 16 weeks fully paid parental leave for eligible employees and fertility support through Carrot. These family‑forming benefits are highlighted as competitive for a venture‑backed startup.
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Leave & Time Off Breadth — Listings describe flexible or generous PTO, 13 paid holidays with a year‑end holiday break, and front‑loaded sick time. Remote‑friendly policies and stipends also support practical work‑life rhythm.
Headway Insights
What We Do
Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.
Why Work With Us
The demand for mental health care has never been higher, underscoring the need for solutions like Headway that increase accessibility to clinical care. 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.
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Headway Offices
Remote Workspace
Employees work remotely.
Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle.
