Head of Security Engineering

About This Opportunity

We are representing a confidential telehealth organization seeking a Head of Security Engineering to lead their security strategy with a strong emphasis on offensive security and attacker mindset. This is a remote position based in the USA, reporting directly to senior leadership.

Our client operates at significant scale in a highly regulated environment where security, privacy, and customer trust are paramount. This role will anchor their security organization in a red team–first approach, proactively identifying vulnerabilities and strengthening defenses before they can be exploited.

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.

Responsibilities

• Lead the organization'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 red team capabilities, including penetration testing, code review, and vulnerability discovery
• Provide oversight and guidance across Security Operations (blue team) and Application Security functions
• Partner closely with Engineering to embed security into the software development lifecycle
• Strengthen processes around vulnerability management, detection, and response
• Build and improve offensive security tooling and capabilities, complementing external bug bounty programs
• Reduce technical debt and improve system resilience through proactive security practices
• Identify and address emerging threats, including AI security risks
• Mentor and guide a security team, setting a high bar for technical rigor and impact

What We're Looking For

Required Qualifications:

• 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

Preferred Qualifications:

• Experience with AI/ML security or emerging attack vectors
• Experience working with PHI/PII in healthcare or regulated environments
• 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

How We Work With You

When you apply through Get A Job.ai, our talent team will review your background and conduct an initial screening conversation. If there's a strong match, we'll submit your profile to our client for consideration and guide you through their interview process.

Important: Please do not attempt to contact the employer directly. All communication regarding this opportunity should go through Get A Job.ai to ensure proper representation and coordination.

This is a remote position with employees asked to travel to the company's California office up to three times per year, plus one company-wide offsite. Travel expenses are covered by the employer.

Pay

Pay via Get A Job.ai: $250,000 - $300,000 base salary, plus performance bonus and comprehensive benefits including health/dental/vision coverage, 401k with employer match, and wellness perks.

Equal Opportunity: Get A Job.ai is committed to inclusive hiring practices. We welcome candidates of all backgrounds and work with clients who share our commitment to equal opportunity employment.