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. What will you do? • 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: • 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 What will you NOT do? • You will NOT worry about "runway", "cash left", or "how much time we have until the next round". We have the startup DNA but we're fully backed and funded, all the way to success. • You will NOT be confined to your "job". You will get involved in product, marketing, business strategy, and almost everything we do. • You will NOT be bogged down by office politics, ego, or bad attitude. Only positive, pleasure-to-work-with people are allowed here! • You will NOT get yourself burned out. We work hard but we believe in maintaining a sustainable work/life balance. Really. Can I work remotely? Yes. We operate on PST and candidates in any time zone are welcome to apply. We ask employees to travel to our San Jose, CA office up to three times per year plus one company-wide offsite to collaborate in person and strengthen working relationships. Travel expenses are covered and reasonable accommodations are made for those under unique circumstances who cannot travel. 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 Benefits • Remote work with regular in-person bonding experiences sponsored by the company • Competitive compensation • Holistic perks program (including free therapy, employee wellness, and more) • Excellent health, dental, and vision coverage • 401k benefits with employer matching contribution • The chance to build something that changes lives - and that people love • Any piece of hardware or software that will make you happy and productive • An awesome community of co-workers Bonus (Great to have, but not required) • 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 The base salary range for this position is $250,000 - $300,000. In addition to the base salary, this position is eligible for a performance bonus and the extensive benefits listed here (subject to eligibility requirements): Teladoc Health Benefits 2025. Total compensation is based on several factors - including, but not limited to, type of position, location, education level, work experience, and certifications. This information is applicable to all full-time positions.