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 (~85) 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 therapist 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

About the Engineering Foundations Group at Headway

The Engineering Foundations Group at Headway empowers engineering and product teams to deliver better, faster outcomes. We achieve this by building robust platforms, efficient tools, and streamlined processes that enhance productivity, maintainability, and quality. As a key part of Headway’s Engineering Organization, Eng Foundations consists of specialized pods that enable scalable growth, operational excellence, and product-driven innovation. By providing the core infrastructure and frameworks our teams rely on, we accelerate Headway’s mission to transform mental healthcare.

About the Web Platform Pod

As our Engineering Foundations Group grows, we’re excited to establish a new Web Platform Pod to elevate how we build web applications at Headway. This team will:

• Standardize our growing suite of web applications on a unified stack, ensuring consistency, reliability, and maintainability.
• Empower developers with robust tooling, clear guidelines, and automated processes to streamline development and enforce web standards.
• Enhance observability and performance monitoring to optimize user experience, accessibility, and scalability.
• Automate testing frameworks to improve code quality and prevent regressions.
• Enable rapid experimentation by building infrastructure that supports A/B testing, feature flagging, and data-driven iteration, ensuring teams can validate hypotheses quickly and safely

Who you are

We’re looking for experienced engineering team leaders and people managers who are relationship-obsessed, drive results and enable their teams to build for technical excellence. As Engineering Manager of the Web Platform Pod, you will:

• Set the vision and strategy for how web development is standardized and scaled at Headway.
• Lead and grow a high-impact team, fostering a culture of excellence, collaboration, and innovation.
• Drive adoption of best practices across all product engineering teams, ensuring high-quality, accessible, and scalable web applications.
• Develop and maintain experimentation frameworks, providing engineers and product teams with the tools to run A/B tests, gradual rollouts, and controlled experiments.
• Collaborate with cross-functional partners (Eng, Product, Design, Growth, Customer Success) to deeply understand user needs and ensure the platform delivers exceptional value.
• Measure and improve impact by defining KPIs, gathering feedback, and iterating on platform capabilities.

This is an opportunity to shape the future of Headway’s web development ecosystem and make a lasting impact in a fast-paced environment. Your leadership will directly influence Headway’s mission, engineering velocity, and developer experience.

Below are some additional experiences we think help this engineering manager succeed at Headway:

• 4+ years of people management experience in an engineering leadership role, with prior experience in frontend or fullstack engineering.
• Experience leading cross-functional teams and working collaboratively with product, design, and other engineering teams.
• Ability to mentor and guide engineers, fostering technical excellence and a culture of continuous learning.
• Passionate about building scalable, reliable, and maintainable systems that abstract complexity and empower teams.
• Strong technical intuition—able to navigate and discuss engineering tradeoffs related to timelines, resources, and long-term maintainability.
• Deep understanding of modern web technologies, including their strengths, tradeoffs, and best practices.
• Experience designing and building frontend infrastructure and platform capabilities to support scalable web applications.
• Strong foundation in performance optimization, observability, and security practices for web applications.
• Experience with frontend testing strategies (e.g., unit, integration, and end-to-end testing) and CI/CD automation for web applications.
• Comfortable with ambiguity and thrives in a fast-paced, high-growth environment.

Nice-to-Have:

• Hands-on experience with A/B testing, feature flagging, and experimentation frameworks.
• Familiarity with modern web stacks (e.g., React, Next.js, TypeScript) and frontend build systems.
• Experience in developer productivity tooling, including performance monitoring, automated testing, and CI/CD pipelines.
• Knowledge of progressive web apps (PWAs), accessibility standards (WCAG), and SEO best practices.
• Experience with cloud platforms (AWS, GCP) and edge computing/CDN strategies for frontend performance.
• BS, MS in Computer Science or related field

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 rounds: You’ll meet with an engineering leader on the team to go deeper into your technical and people leadership experiences
• Final rounds: You’ll meet several more team members for one technical and multiple behavioral interviews, leaving you 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:

• Salary information is based on a single salary target per role, and the starting salary for Engineering Managers is $200,000 and can increase to $238,000 based on industry tenure and experience.
• 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

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