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 (~120) 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 this role

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.

This role sits at the intersection of product development, user experience, and patient activation. You’ll have the freedom to innovate and experiment while collaborating with a diverse group of cross-functional partners from across the company. This is an opportunity to tackle complex, rewarding problems in a highly collaborative, supportive environment that values technical excellence and operational rigor. Your teams will build systems that help patients discover and access mental health care, directly improving lives and transforming the healthcare landscape. Your work in this role will shape how thousands of patients connect with care, making a lasting impact on Headway’s mission to reimagine mental healthcare access for all.

As an engineering leader at Headway, you will be responsible for leading and growing the team behind these core growth initiatives through people development, strategic planning, and hands-on technical support. You’ll play a leading role in defining what and how these systems are built, setting up how the team operates, and ultimately driving best-in-class experiences that convert interest into action.

By helping more patients get activated on Headway — connecting them with the right provider, at the right time, and setting them up for successful ongoing care — you’ll directly impact how effectively we fulfill our mission of making mental healthcare accessible to all.

Who you are

We’re looking for experienced engineering team leaders and people managers who are product-minded, data-informed, and energized by growth. As an Engineering Manager at Headway, you will work closely with Engineering Leadership, Product, Design, Data, and Operations to shape the future of our patient activation experience — ensuring that new patients are successfully guided to the right care and continue their journey on Headway. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact at a high-growth company.

• Lead and manage an engineering team focused on patient activation, building intuitive, high-quality consumer experiences that help new patients find and continue care with the right providers.
• Build and scale the team as Headway deepens its investment in this critical area of growth.
• Partner closely with Product, Design, Data and Operations to rapidly iterate through A/B testing
• Drive alignment across your team on process, prioritization, and product outcomes
• Develop and grow your team through weekly 1-1s, mentorship, and feedback
• Work with and help develop aspiring engineering leaders within the engineering team
• Contribute to the broader company strategy and product roadmap
• Help build out our engineering team as the headcount grows from 120 to 175+ through the remainder of the year

Below are additional experiences we think help engineering managers succeed at Headway:

• You have 3+ years of experience as an experienced Engineering Manager at a high-growth startup or scale-up
• You have 3-5+ years of experience as a Software Engineer
• You’re energized by experimentation and growth — and can balance short-term learning with long-term scale
• You have a strong product mindset and have built strong cross-functional relationships that drive optimal user experiences and build trust with users
• You have a strong technical foundation that allows you to ensure your team is making appropriate technical decisions
• You have a track record of building and leading high performing teams that have effectively delivered business outcomes through technical investments
• You have a track record of working well across teams and functions
• You are flexible and adaptable; you understand that the best growth teams must learn and iterate quickly, and that growth roadmaps are dynamic as a result

Nice to have: Prior experience building and optimizing consumer-facing activation or onboarding flows

• Nice to have: Prior experience with Python and React and working with AWS infrastructure
• Nice to have: Experience in health tech, building user-facing products
• 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 team and people leadership experiences and complete one technical (systems design) interview.
• Final rounds: You’ll meet team members across product and engineering leadership for 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:

The expected base pay range for this position is $198,050 - $233,000, 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