About the role:
Reporting to Headway’s Director of Security, you’ll have the opportunity to build and grow a world-class engineering team focused on securing the products and applications that powers Headway. You’ll own our approach to application security, secure software development, and product-integrated security strategy across all aspects of Headway’s services, systems, and user experiences.
Your team will be responsible for driving application-layer and product security efforts at scale. You’ll lead the development of security features, tooling, and programs that enable our product and engineering teams to ship secure code and protect sensitive data throughout the software development lifecycle. You’ll build and grow a pod through strategic planning, recruiting/hiring, people development, leading high-impact initiatives, and reporting on outcomes.
Your work will be deeply cross-functional, partnering closely with product, platform, and core engineering teams. You’ll help teams bake security into product design, introduce secure-by-default tools and practices, and enable scalable threat modeling, secure coding, and proactive vulnerability management. You’ll also collaborate with IT, infrastructure, and compliance teams to align product security goals with broader organizational risk and trust objectives.
What you’ll do:
- Own Headway’s application and product security strategy, setting the vision and roadmap for securing all customer- and provider-facing experiences.
- Build a best-in-class application security program that embeds secure development practices into the software development lifecycle (SDLC), including threat modeling, secure code reviews, and automated security testing.
- Drive initiatives to improve security visibility and response within our products, including user-access controls, sensitive data handling, and in-app protections.
- Partner with product and engineering teams to identify and mitigate risks in new features, third-party integrations, and architectural decisions. Act as a trusted advisor to engineering teams, fostering a culture of ownership, accountability, and security best practices.
- Build tools, workflows, and documentation that help engineers write secure code and own their security responsibilities.
- Create a highly engaged, operationally and technically excellent engineering culture within your pod.
- Align product and platform engineering teams to security goals with regulatory, privacy, and compliance requirements; collaborating closely with privacy, legal, and compliance teams.
- Support production incident response processes in partnership with engineering and Trust teams, helping to triage, remediate, and learn from security events.
You will love this role if:
- You’ve managed or led security engineering teams and are excited to build and grow one from the ground up.
- You have a strong background in application security and secure development practices, and have partnered closely with engineering teams.
- You enjoy enabling developers to build safely and quickly through secure-by-default tooling and clear guidance.
- You’re comfortable working across domains—from product design to AWS infrastructure—using security as a force multiplier.
- You thrive in highly collaborative environments and care deeply about empowering teams to do their best work securely.
- You’re motivated by Headway’s mission to make mental healthcare more accessible and want to make a positive impact through security.
Tools We Use:
- Languages: Python 3, TypeScript
- Frameworks & Libraries: FastAPI, React/Remix, SQLAlchemy
- Cloud Infrastructure: AWS (ECS, RDS, S3), Kafka
- Security Tooling: Semgrep, Wiz, Expel, Datadog
- Access Management: Okta, Auth0, Teleport
- Monitoring & Incident Response: Datadog, PagerDuty
- Source Control: GitHub
- WAF & Networking: Cloudflare
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 $227,000 - $267,000, 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
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