Staff Software Engineer, Payer

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, React, Remix, Next.js, React Aria
• 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. Our teams work on high-leverage problems at the intersection of scale, healthcare complexity, and real-world impact—often without the safety net of large, fully staffed orgs. What makes this work unique is that, as the largest provider network in the U.S., we have a rare opportunity to prove to the market that this model can work—and that it meaningfully improves care.

• Our Payers and Outcomes group is making early, foundational architecture decisions that will shape how Headway scales and how we integrate with payers and measure outcomes over the long term. We’re building the technology that allows us not just to identify risk, but to actively support providers in doing better work—starting with operational areas like coding and billing, and extending into much more nuanced clinical practice.
• In partnership with top clinicians, we are developing applied LLM systems that can deliver actionable, trustworthy feedback to providers: helping them improve documentation, reduce administrative burden, and ultimately raise the level of care toward more evidence-based and value-based practice. This requires balancing automation with explainability and trust in a highly regulated environment.
• At the same time, we are tackling the “one-size-fits-none” problem in mental healthcare. We recognize that providers have different strengths and areas of excellence, and we are building systems that match patient acuity to those strengths—so patients receive the right level of care and providers can operate at the top of their license.
• There is still much to do. But this work represents a true paradigm shift for mental healthcare in the U.S.—a generational change in how quality, outcomes, and access are aligned. This is the technology we are building, and this is the impact we are here to drive.

These initiatives reflect how we operate: small teams, high ownership, technically deep problems, and outcomes that matter—to the business, providers, and patients alike.

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:

• Has designed and scaled ML / LLM-powered systems in production
• Architected complex systems spanning multiple technical domains or product areas (e.g., publishing npm packages or owning infrastructure depended on by multiple teams)
• Driven technical vision and strategy at the organization level, by writing and reviewing technical design documents and participating in quarterly planning activities
• 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 $224,000 - $280,000, 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