Staff Software Engineer

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 45,000 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.

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 engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide.  The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

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

Projects we’re working on:

At Headway, we treat infrastructure and developer experience as force multipliers. Here’s a look at the core engineering initiatives that enable us to move fast, deliver reliably, and scale responsibly:

• Platform Architecture & Scalability: Modularize the backend (Mamba) to enable pod-level autonomy via clear ownership boundaries, standardized observability, and scalable infrastructure patterns.
  
  
• Developer Experience & Agentic Tooling: Build agentic tooling and abstractions to eliminate low-leverage tasks (e.g., smart test generation, scaffolders, code-aware search), improve CI/CD velocity and stability, surface actionable metrics (e.g., PR throughput, review latency), and standardize local environments and dev scaffolding.
  
  
• Web Platform & UI Architecture: Standardize all core web apps on a unified stack (e.g., Headway design system, Remix), scale adoption of shared components and testing patterns (unit, integration, E2E), simplify state management and architecture, and enforce performance, accessibility, and security standards.
  
  
• Observability & Quality: Expand proactive observability through SLOs, dashboards, and structured alerts, integrate real user monitoring (RUM), and link telemetry with test coverage to prioritize reliability improvements based on user impact.
  
  
• Communications Platform: Empower product teams to own and experiment with customer messaging via event-based workflows and reusable compliant templates for email, SMS, and secure messaging.

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.

For all engineers:

• You have experience working across the stack on modern web applications
• Strong understanding of at least one programming language and comfortability with others
• Shaped work to achieve company and team goals
• Flexed into new technical and non-technical areas as projects require
• Committed team member supporting the growth of those around them

For staff engineers:

• Architected complex systems spanning multiple technical domains or product areas
• Driven technical vision and strategy at the organization level
• Established engineering standards and best practices across multiple teams
• Led major technical initiatives requiring coordination across multiple teams
• Mentored senior engineers and technical leaders

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 

First round: You'll meet with an engineer on the team to do some live coding and learn more about the engineering team.

Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway.

References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation and Benefits:

The expected base pay range for this position is $233,000- $276,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and 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

#LI-BM1

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 employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.