Senior Engineering Manager (Trust Foundations - Data Security)

Building for trust is non-negotiable in our mission of making mental healthcare more accessible. Fundamental to this is safeguarding our users' sensitive data. The Trust Foundations team is responsible for building the secure, auditable, and privacy-first platforms that all of Headway’s product teams rely on to innovate safely and quickly.

As the Senior Engineering Manager for our new Secure Defaults pod, you will own the vision for and lead the team tasked with protecting Headway's most sensitive data. You will be responsible for setting the long-term strategy for how we handle data security at scale, spearheading foundational initiatives in data lineage, classification of sensitive information (PHI), and building the next generation of our Role-Based Access Control (RBAC) primitives. A key, forward-looking part of this role will be to define the roadmap for the secure and compliant use of AI at Headway.

This is a critical leadership role for a passionate, mission-aligned engineering leader to build a new team and make an immediate impact on Headway’s ability to scale securely.

• 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.

• Languages: Python 3, TypeScript
• Libraries: FastAPI, SQLAlchemy, React, Remix, Next.js
• Datastores: Postgres, Redis
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark, Flink, and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github, PagerDuty
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework

As a Senior Engineering Manager on the Trust Foundations team at Headway, you're a security-minded leader passionate about developing engineers and fostering a culture of technical excellence, collaboration, and results. You lead from the front, taking full ownership of your team’s roadmap and strategy. Comfortable diving into the technical details, you will guide your team with dedicated mentorship while staying relentlessly focused on building products that deliver real value to our users.

• Lead, develop, and mentor a team of 5+ engineers, guiding their career growth through continuous feedback and dedicated 1-1s, and support hiring as we scale engineering from 120 to 175+ in the coming year
• Own your team's strategy and roadmap, ensuring its alignment with broader company objectives and driving execution to deliver results.
• Develop future leaders by identifying and mentoring aspiring technical leaders, contributing to the growth of talent across the entire engineering organization.

• You have a track record of building and leading high-performing teams, with 5+ years of experience as an Engineering Manager built upon a 4-5+ year background as a hands-on Software Engineer.
• You are a deep domain expert in data security architecture. You have proven, practical experience designing and delivering systems for data lineage, classification of sensitive data (like PHI), and de-identification at scale.
• You think in platforms and primitives. You have a demonstrated history of building secure-by-default foundations (e.g., RBAC systems, data access layers) and internal tooling that empowers other engineering teams to move faster and more safely.
• You are a forward-looking, strategic thinker. You have an informed perspective on the future of data security, including the challenges and opportunities of applying AI to solve these complex problems in a safe and compliant way.
• You are a pragmatic partner with a strong product mindset. You know how to balance robust security principles with the needs of a rapidly scaling business and can collaborate effectively with stakeholders in Legal, Security, and Product to deliver clear business outcomes through your technical investments.
• 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

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 Trust and Engineering 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!

The expected base pay range for this position is $234,600 - $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.

• 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