Engineering Manager (Data Safety)

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 75,000 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, Spark Capital, 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.

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!).

• 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 iterating.
• 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, SageMaker and more), Spark and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework

About This Role

Headway's mission is to build a new mental healthcare system that everyone can access. The data we hold to do that is some of the most sensitive there is: what someone said in therapy. Data Safety is the team that makes it possible to learn from that data without putting the people in it at risk. As Engineering Manager for Data Safety, you'll lead that team. Protecting patient data is Headway's first priority, ahead of any roadmap, and that is not a slogan here: it is the constraint every other team designs around. Your job is to turn that constraint into something people can build on rather than something they route around.

The upside is enormous. With tens of thousands of providers and millions of sessions, Headway holds what is very likely the richest picture of real mental health care anywhere in the world. Remarkably little is known at scale about which care helps whom, and we are sitting on the data that could answer it. The blocker has never been curiosity, it is having a safe way in. The core of that is de-identification: removing the person from the record while keeping the clinical signal, and getting the method certified so the whole company can rely on it.

You'll grow and mentor a team of roughly five to eight engineers, set the roadmap for the pod, and work closely with Security, Legal, Compliance, Data, and the product teams that depend on you. The bar is high. We have to be able to stand behind how we handle this data to a regulator, to a payer, and to the patient it came from. Get that right and what your team ships sets the ceiling on how much Headway can learn, and on how many people we can help.

Responsibilities

• Lead, manage, and grow the Data Safety engineering team
• Own delivery on privacy and compliance commitments, including their audit evidence
• Set the technical and operational roadmap across de-identification, data access tiers, entitlements, and LLM data handling
• Develop your team through weekly 1:1s, mentorship, and direct feedback, and grow a tech-lead layer beneath you
• Partner closely with Security, Privacy and Compliance, Legal, Data Platform, and product pods to move quickly and safely
• Contribute to the broader group and company strategy, not just your own roadmap

Requirements

• 3+ years of engineering management experience at a high-growth startup or scale-up
• 4+ years of experience as a software engineer, enough to hold technical direction credibly
• A track record of building and leading high-performing teams that delivered business outcomes through technical investment
• A strong product mindset and cross-functional relationships that build trust with users and stakeholders
• Experience shipping under real compliance or audit pressure, with the scope discipline that requires
• Comfort with data platform and privacy systems: access control, data classification, pipelines, and de-identification

Nice to have

• Healthcare, financial services, or another regulated, high-trust domain
• HIPAA de-identification, tokenisation, differential privacy, or data governance tooling
• Prior experience with Python, React, and AWS infrastructure

Why You'll Love This Role

• Lead the team that decides what the rest of the company can safely learn from its data
• Own commitments the company is accountable for to regulators, auditors, and partners
• Build a tech-lead layer beneath you rather than inherit a finished team

Pay

The expected base pay range for this position is $222,800 - $278,500, 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.

Benefits

• 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