Job Title:

Director of Penetration Testing

Department:

Offensive Security / Cybersecurity

Reports To:

VP of Cybersecurity / Chief Information Security Officer (CISO)

Location:

Hybrid/Flexible (with travel as needed)

Role Overview:

The Director of Penetration Testing is responsible for leading and scaling the organization’s penetration testing practice, ensuring the delivery of high-quality security assessments. This role combines technical expertise, leadership skills, and strategic vision to manage a team of penetration testers, develop testing methodologies, and provide actionable insights to strengthen the organization’s security posture. The director will also serve as a trusted advisor to internal stakeholders and clients on offensive security matters.

Key Responsibilities:

Leadership & Strategy:

•Define and execute the strategic vision for the penetration testing program.

•Build, manage, and mentor a team of highly skilled penetration testers.

•Drive innovation in tools, techniques, and methodologies to stay ahead of emerging threats.

•Represent the penetration testing team in senior leadership and client-facing discussions.

Operational Management:

•Oversee the planning, execution, and delivery of penetration testing engagements, including network, application, cloud, mobile, and IoT assessments.

•Ensure testing is conducted in compliance with industry standards and regulatory requirements.

•Manage the development and maintenance of internal testing tools, frameworks, and scripts.

•Monitor team performance and ensure alignment with organizational goals and KPIs.

Collaboration & Stakeholder Engagement:

•Partner with other cybersecurity teams (e.g., threat intelligence, incident response) to enhance the organization’s offensive security capabilities.

•Communicate findings and remediation strategies to technical and non-technical audiences, including executives and board members.

•Support the development of security policies and standards based on testing insights.

Business Development:

•Support the growth of the penetration testing practice by identifying new business opportunities and building client relationships.

•Assist in scoping engagements, preparing proposals, and participating in client presentations.

Risk Management & Reporting:

•Deliver detailed reports outlining vulnerabilities, risks, and recommended mitigation strategies.

•Prioritize findings based on business impact and collaborate with teams to drive remediation efforts.

•Track and validate the resolution of identified issues.

Skills & Qualifications:

Technical Expertise:

•Deep understanding of penetration testing tools and techniques (e.g., Burp Suite, Metasploit, Cobalt Strike, Nessus).

•Expertise in vulnerability assessment, exploit development, and security testing across diverse environments (on-premise, cloud, hybrid).

•Familiarity with frameworks and standards like OWASP Top Ten, MITRE ATT&CK, NIST, and PCI DSS.

•Experience in reverse engineering, fuzzing, or red teaming is a plus.

Leadership & Communication:

•Proven experience leading and managing penetration testing teams or offensive security programs.

•Strong communication skills, with the ability to articulate complex technical findings to non-technical stakeholders.

•Experience building and maintaining cross-functional relationships with technical and business leaders.

Essential Skills:

•Ability to think creatively and adopt an adversarial mindset.

•Strong project management skills, including the ability to handle multiple engagements simultaneously.

•Attention to detail and a commitment to delivering high-quality results.

Qualifications:

•Bachelor’s or Master’s degree in cybersecurity, computer science, or related field.

•Relevant certifications such as OSCP, OSCE, CREST CCT, GPEN, GXPN, or equivalent.

•Additional certifications (e.g., CISSP, CISM) are advantageous.

Key Attributes:

•Strategic thinker with a hands-on approach when necessary.

•Passionate about offensive security and driving innovation in testing techniques.

•Collaborative, ethical, and committed to fostering a positive team culture.

•Resilient and adaptable, with the ability to manage pressure in high-stakes environments.