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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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 the role
Most therapists who join Headway bring their own clients, through referrals, directories, their own websites, and word of mouth. The Provider-Sourced Clients (PSC) team builds the products that help providers fill their caseload and run their whole practice on Headway. We're building growth tools providers actively use: AI agents that answer and convert patient inquiries, tools that make moving an existing caseload to Headway effortless, marketing tools for clinicians who aren't marketers, and routing that gets every patient to the right provider in our network.
You'll own the architecture behind how Headway helps providers capture, convert, and keep their own clients. You'll design the platform to support lead management, lead technical direction on porting and caseload tooling, and work with product and data to decide which bets to make and how to measure them. The role is highly cross-functional: you'll partner with product, design, data, Sales, CX, and pricing teams, and your work will directly drive one of Headway's top company goals.
Who you are
A systems thinker who designs platforms that several teams build on and guides others through them
An engineer who has shipped AI-powered, user-facing products and knows what makes them reliable
A product-minded partner who cares about outcomes and will kill a project that isn't moving the metric
A communicator who makes technical trade-offs legible to non-technical partners
A leader who earns influence through technical depth and leaves teams stronger than they found them
Experience we're seeking
8+ years of software engineering experience
Built and scaled user-facing products in a marketplace, vertical SaaS, or health-tech environment
Shipped LLM-powered agents or workflows in production, including evals, guardrails, and human-in-the-loop design
Experience with data-heavy onboarding: imports, migrations, CRM/lead systems, or integrations with third-party systems
Comfortable running experiments and instrumenting product impact
Demonstrated ability to shape technical direction across teams without direct authority
Nice to have: healthcare or insurance domain experience
Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.
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 software engineering experience
- Experience building and scaling user-facing products in a marketplace, vertical SaaS, or health-tech environment
- Production experience shipping LLM-powered agents or workflows, including evaluations, guardrails, and human-in-the-loop design
- Experience with data-heavy onboarding, imports, migrations, CRM or lead systems, or third-party integrations
- Experience running experiments and instrumenting product impact
- Ability to shape technical direction across teams without direct authority
- Healthcare or insurance domain experience
What the Team is Saying
Headway Compensation & Benefits Highlights
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Healthcare Strength — Health coverage for corporate employees is presented as robust, with multiple medical, dental, and vision options and the company covering a majority of premiums. Standard protections such as life and short- and long-term disability insurance are also included.
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Parental & Family Support — Paid parental leave is described as up to 16 weeks at full pay for eligible employees. Family-forming support through Carrot Fertility further expands coverage for diverse parenting needs.
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Wellbeing & Lifestyle Benefits — Wellbeing offerings include therapy-cost reimbursement, an employee assistance program, and remote-work stipends alongside flexible PTO and paid holidays. These benefits provide day-to-day support that complements core insurance.
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.
