Staff Software Engineer (Journeys)

About the role

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.

Principles That Guide US

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapists to better solve the problems they’re facing.
• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools We Use

• Languages: Python 3, TypeScript
• Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js
• Datastores: Postgres, Redis
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github, PagerDuty
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework
• Delivery: Knock (transactional + product notifications), Iterable (lifecycle marketing + campaigns), Twilio, Mailgun

Who You Are

• We’re looking for experienced engineers who have the ability to deal with ambiguity and learn new technologies and systems. Below are some additional experiences we think help engineers succeed at Headway.
• A systems thinker who holds the architecture of a complex, multi-vendor platform and guides the team through it
• An engineer who has shipped high-throughput, event-driven systems in production and knows what reliability requires
• A communicator who translates technical trade-offs for non-technical stakeholders and drives alignment across marketing, product, and engineering
• Genuinely excited about the intersection of AI and communications - and thoughtful about what makes AI-in-the-loop systems reliable at scale
• A leader who earns influence through technical depth and leaves teams more capable than they found them
• Experience we’re seeking
• 8+ years of software engineering experience, with meaningful time at Staff-level or equivalent
• Designed and built high-volume, event-driven communications platforms - email, SMS, push, or equivalent - at millions of events per month
• Fluency with multi-vendor delivery stacks; strong opinions about build-vs-buy trade-offs at the platform layer
• Experience building or working closely with experimentation infrastructure - A/B testing, engagement analytics, personalization, or recommendation systems
• Exposure to LLM-powered systems in production - not just API consumption, but thinking about reliability, latency, and quality at scale
• Demonstrated ability to shape technical direction across teams without direct authority

• Headway participates in E-Verify. To learn more,
• 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.