Lead Director, Adversary Operations

At CVS Health, we’re building a world of health around every consumer and surrounding ourselves with dedicated colleagues who are passionate about transforming health care.

As the nation’s leading health solutions company, we reach millions of Americans through our local presence, digital channels and more than 300,000 purpose-driven colleagues – caring for people where, when and how they choose in a way that is uniquely more connected, more convenient and more compassionate. And we do it all with heart, each and every day.

Who You Are

• Experienced Penetration Tester: Deep expertise in conducting internal penetration testing, including both remote and on-site assessments, to identify vulnerabilities within networks, applications, and physical security controls.
• Offensive Security Expert: Proficient in using tools like Kali Linux, Metasploit, Burp Suite, and other penetration testing frameworks. Knowledge of scripting and automation to streamline testing processes.
• Cybersecurity Operations Veteran: Extensive experience in managing and optimizing Security Operations Centers (SOCs), implementing effective security monitoring, and coordinating incident response efforts.
• Threat Intelligence Integrator: Skilled at leveraging threat intelligence to inform testing strategies, prioritize threats, and adapt penetration testing techniques based on emerging adversary tactics.
• Incident Response Leader: Proven track record of leading or collaborating with incident response teams to contain and remediate security incidents swiftly. Experience in conducting post-incident reviews and refining detection capabilities.
• Collaborative Leader: Proven ability to work closely with blue teams and other cybersecurity functions to enhance detection capabilities, improve incident response, and reduce overall organizational risk.
• Risk-Focused: Skilled in evaluating security risks and recommending actionable solutions that align with business objectives.
• Compliance and Governance Aware: Experienced in ensuring that penetration testing and security operations align with regulatory and compliance requirements, such as PCI-DSS, HIPAA, NIST, and ISO 27001.
• Innovator: Passionate about integrating offensive security practices into a comprehensive threat management strategy.

Role Responsibilities

Penetration Testing & Adversary Emulation

• Lead and manage internal penetration testing efforts, simulating real-world attack scenarios to uncover security weaknesses.
• Develop and execute adversary emulation exercises to test the organization’s detection and response capabilities.
• Utilize and maintain a comprehensive suite of penetration testing tools, including Kali Linux, Metasploit, Nmap, and custom scripts.
• Conduct physical security assessments as required, evaluating access controls, surveillance systems, and physical safeguards.

Collaboration & Purple Teaming

• Work closely with blue teams to design and implement purple team exercises that bridge offensive and defensive security efforts.
• Provide actionable insights to improve security monitoring, alerting, and incident response based on penetration testing results.
• Facilitate knowledge sharing sessions to upskill internal teams on adversary tactics, techniques, and procedures (TTPs).

Security Strategy & Risk Management

• Develop a comprehensive adversary operations strategy aligned with organizational risk management goals.
• Provide executive leadership with detailed reports on security gaps, risks, and the effectiveness of security controls.
• Prioritize remediation efforts based on risk impact and operational feasibility.

Tool Development & Automation

• Automate common penetration testing tasks using Python, PowerShell, or Bash scripting to increase efficiency.
• Contribute to the development of custom tools for red teaming and penetration testing.

Incident Response Support

• Assist the incident response team by providing adversary tactics insights during active investigations.
• Collaborate on developing threat hunting use cases and refining detection capabilities based on attack simulations.

Required Qualifications

• 10+ years of experience in cybersecurity with a focus on offensive security, penetration testing, and/or red teaming.
• 5+ years of experience in Kali Linux, Metasploit, Nmap, Burp Suite, and/or other similar security tooling.
• 5+ years of experience in scripting (PowerShell, Python, etc.)
• 3+ years of experience with cloud security (AWS, Azure, GCP) and container security.

Preferred Qualifications

• Relevant certifications such as