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 70,000 providers across all 50 states run their practice on our software, serving over 1 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. 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, GV, 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. 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 At Headway, we’re building a national network of therapists who accept insurance — and making mental healthcare radically more accessible in the process. Supporting providers isn’t just about connecting them with patients — it’s about delivering the tools they need to manage their practice with ease, confidence, and compliance. Our providers are the heart of Headway’s mission — and empowering them with an easy-to-use platform is critical to both their success and the quality of care patients receive. Whether it’s saving providers time, simplifying documentation, or ensuring compliance, this role is at the center of our providers’ lives. As an engineering leader at Headway, you will be responsible for leading and growing the engineering pods behind our core provider experiences through people development, strategic planning, and hands-on technical support or guidance. You get to play a leading role in defining what and how these teams build, setting up how the teams operate, support, and ultimately drive best-in-class user experiences that have a measurable impact on our ability to execute and meet the demands of a high growth startup. This is a critical leadership role for Headway and our mission to make mental healthcare more accessible. By helping providers spend less time on administrative tasks and more time on care, you’ll directly support both provider satisfaction and patient access. 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 a Senior Engineering Manager at Headway, you will work closely with Engineering Leadership, Product, Design and Business teams to help shape the future of the engineering organization. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact on our rapidly scaling engineering team. - Lead and managed engineering teams of 12+ engineers - Lead and managed multiple pods, as well as other engineering managers - Ensure there is process and product alignment across your team - 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 5-7+ years of experience as an experienced Engineering Manager, concurrently leading multiple teams, and/or managing managers - You have 3-5+ years of experience as a Software Engineer - 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 - It's a nice to have if you've had prior experience with Python and React and working with AWS infrastructure - It's a nice to have if you've had 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 $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 #LI-AC1 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 participates in E-Verify. To learn more, click here. A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. 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.