Staff Software Engineer

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.

• 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, * 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.

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.