Senior Security Engineer

Summary

Join Headway's Trust team as a Security Engineer and play a foundational role in building incident response and security operations capabilities. Lead security incident response readiness and execution by designing, building, and refining processes, playbooks, tooling, and automations. Automate security workflows to streamline detection, triage, investigation, and response. Mitigate identified risks by working with Engineering and Trust teams. Build and maintain response infrastructure, ensuring comprehensive visibility across environments. Support broader security operations, contributing to vulnerability management and security reviews. This role requires deep incident response experience, a passion for automation, a strong engineering foundation, the ability to thrive in ambiguous environments, and excellent collaboration skills. Headway offers a competitive salary, equity compensation, comprehensive benefits, and a meaningful mission.

Requirements

• Have deep incident response experience: You’ve led or contributed to major security incident investigations and developed playbooks, processes, and tooling to improve response
• Are passionate about automation: You’ve built or implemented automated workflows that reduce MTTR (mean time to respond) and increase consistency in security operations
• Have a strong engineering foundation: You’re comfortable writing production-quality code and building internal tools and systems in support of security operations
• Thrive in ambiguous environments: You enjoy solving problems without a defined path and bring a pragmatic, fast-moving mindset to security engineering
• Collaborate well across teams: You’re proactive in working with IT, infrastructure, and product engineers to drive scalable solutions to shared security challenges
• Care deeply about impact: You want your work to contribute directly to a meaningful mission—improving access to mental healthcare

Responsibilities

• Lead security incident response readiness and execution: Design, build, and refine our incident response processes, including playbooks, tooling, and automations that reduce manual overhead and speed up remediation
• Automate security workflows: Develop scalable automations that streamline detection triage, investigation, and response, integrating with internal systems and third-party platforms
• ���Close the loop” by mitigating identified risks: Work with Engineering and Trust teams to remediate risks identified during and after the lifecycle of a security incident
• Build and maintain response infrastructure: Own the systems and integrations that support real-time alerting, case management, and incident tracking
• Continuously improve event coverage: Ensure comprehensive visibility across our environments (cloud, corporate, SaaS, and endpoints), identify telemetry gaps, and lead efforts to close them
• Support broader security operations: Contribute to vulnerability management, penetration testing coordination, and security reviews, helping to scale Headway’s security posture through automation and repeatable processes

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