What are the responsibilities and job description for the Director, Penetration Testing position at The Custom Group of Companies?
Summary
The Director of Penetration Testing will lead the strategy, execution, and ongoing enhancement of penetration testing activities across a diverse technology landscape, including both cloud-based and on-premise environments.
This individual will oversee testing efforts across business-critical platforms and internal systems. The role includes full lifecycle ownership of external testing partners—ensuring engagements are properly defined, executed, and meet established quality standards. Additionally, the Director will supervise a testing coordinator responsible for scheduling, tracking, and governance of all related activities.
A key focus of this position is the development of an in-house penetration testing capability. This includes establishing frameworks, methodologies, and best practices, while also performing hands-on testing as needed to produce high-quality, defensible results.
This is a hands-on leadership role that blends program ownership, technical expertise, and team development. The Director will be responsible for ensuring the effectiveness of penetration testing as a risk control function, while actively contributing to testing initiatives as the internal capability evolves. The ideal candidate brings strong technical penetration testing experience along with a background in managing structured testing programs and third-party providers.
Responsibilities
The Director of Penetration Testing will lead the strategy, execution, and ongoing enhancement of penetration testing activities across a diverse technology landscape, including both cloud-based and on-premise environments.
This individual will oversee testing efforts across business-critical platforms and internal systems. The role includes full lifecycle ownership of external testing partners—ensuring engagements are properly defined, executed, and meet established quality standards. Additionally, the Director will supervise a testing coordinator responsible for scheduling, tracking, and governance of all related activities.
A key focus of this position is the development of an in-house penetration testing capability. This includes establishing frameworks, methodologies, and best practices, while also performing hands-on testing as needed to produce high-quality, defensible results.
This is a hands-on leadership role that blends program ownership, technical expertise, and team development. The Director will be responsible for ensuring the effectiveness of penetration testing as a risk control function, while actively contributing to testing initiatives as the internal capability evolves. The ideal candidate brings strong technical penetration testing experience along with a background in managing structured testing programs and third-party providers.
Responsibilities
- Lead and manage penetration testing efforts across enterprise systems and platforms
- Develop and maintain testing frameworks, standards, and quality metrics
- Establish risk-based priorities, scope, and coverage for testing activities
- Monitor remediation efforts and confirm resolution of identified vulnerabilities
- Oversee the selection and management of testing tools and platforms
- Build internal testing processes, including playbooks, methodologies, and reporting standards
- Perform hands-on testing across applications, APIs, infrastructure, and cloud environments
- Manage external testing vendors, including engagement setup, oversight, and performance evaluation
- Track vendor outcomes and ensure consistent delivery quality
- Define and report on key metrics to assess testing effectiveness (e.g., vulnerability trends, remediation timelines, repeat findings)
- Prepare reporting for senior leadership and stakeholders
- Provide oversight and guidance to the penetration testing coordinator
- Significant experience in cybersecurity, including at least 5 years of hands-on penetration testing
- Demonstrated ability to plan and execute full-cycle penetration tests, from scoping through reporting
- Experience designing and leading penetration testing programs or capabilities
- Background managing third-party security testing vendors and ensuring quality outcomes
- Familiarity with risk-focused environments, ideally within regulated industries
- Strong communication and stakeholder engagement skills
- Proven leadership or mentoring experience with the ability to grow and scale a function
- Relevant certifications in penetration testing or offensive security (e.g., OSCP, GIAC)
- Bachelor's or advanced degree in Cybersecurity, Information Technology, or a related discipline