Head of Security Engineering

BetterHelp

19h•$250,000 - $300,000•Remote

About The Position

BetterHelp is seeking a highly technical Head of Security Engineering to lead our security strategy with a strong emphasis on offensive security and attacker mindset. This role will anchor our security organization in a red team–first approach, proactively identifying vulnerabilities and strengthening our defenses before they can be exploited. In addition to leading offensive security, you will provide oversight and strategic direction across Security Operations (blue team) and Application Security, ensuring a cohesive and effective security posture. This is a hands-on leadership role for someone who thrives in fast-moving environments and can balance deep technical work with broader organizational impact.

Requirements

5+ years of security leadership experience
10+ years of experience in security engineering
Strong background in offensive security (red team, penetration testing, or bug bounty)
Deep understanding of how modern systems are attacked, and how to defend against them
Experience working across or leading Red team, Blue team / SecOps, or Application Security
Experience setting strategy, managing roadmaps, and delivering measurable security outcomes across multiple teams.
Ability to operate both strategically and hands-on
Experience working in fast-paced environments with frequent releases
Strong communication skills with both technical and non-technical stakeholders

Nice To Haves

Experience with AI/ML security or emerging attack vectors
Experience working with PHI/PII
Experience operating in environments with high regulatory, privacy, or customer trust requirements.
Experience building and operating security programs for large-scale cloud, distributed systems, or consumer platforms.
Experience partnering with GRC teams

Responsibilities

Lead BetterHelp’s security engineering strategy, with offensive security as the foundation
Operate with a red team / attacker mindset, identifying vulnerabilities across applications, infrastructure, and internal systems
Direct and evolve the company’s red team capabilities, including penetration testing, code review, and vulnerability discovery
Provide oversight and guidance across Security Operations (blue team) and Application Security
Partner closely with Engineering to embed security into the software development lifecycle (SDLC)
Strengthen processes around vulnerability management, detection, and response
Build and improve offensive security tooling and capabilities, complementing external programs like Bugcrowd
Help reduce technical debt and improve system resilience through proactive security practices
Identify and address emerging threats, including AI security risks
Mentor and guide a strong team, setting a high bar for technical rigor and impact