Lead Penetration Tester (Dep. Director)

Insight Assurance; Remote (OR); Remote; USD 120,000 - 150,000; Full time

Job summary

A leading cybersecurity compliance firm is seeking a seasoned Director of Penetration Testing to oversee a dynamic team focused on enhancing security posture through rigorous testing and innovative strategies. The ideal candidate will bring extensive experience in penetration testing, management skills, and a comprehensive understanding of security frameworks. Join a collaborative remote work culture where your expertise will directly impact organizational success and compliance for diverse clients.

Benefits

Competitive Salary

Flexible Paid Time Off

Performance Bonuses

Flexible remote work environment

Opportunities for professional development

Supportive team culture

Qualifications

• 5+ years of penetration testing experience with managerial experience preferred.
• Proven ability to lead and mentor teams in a cybersecurity context.
• Certificates such as OSCP mandatory; OSCE, OSWE preferred.

Responsibilities

• Lead and manage the penetration testing department.
• Oversee complex penetration tests and red team engagements.
• Develop and enforce testing methodologies and quality standards.

Skills

Penetration Testing

Cybersecurity

Leadership

Technical Report Writing

Risk Analysis

Education

Bachelor’s degree in Cybersecurity, Computer Science, or Information Technology

Tools

Metasploit

Burp Suite

OWASP ZAP

Cobalt Strike

Job description

Insight Assurance is considered one of the fastest-growing companies focusing on cybersecurity compliance. The company is a Florida-registered and licensed CPA firm, PCI Qualified Security Assessor (QSA), and ISO 27001 Certification Body founded by former Big-4 professionals (Former EY), looking to simplify the world of IT compliance. With over 20 years of professional experience working with hundreds of organizations from startups to Fortune 500 companies on a variety of engagements, the team at Insight Assurance partners with organizations looking to meet their organizational and compliance goals.

JOB PURPOSE
We are seeking a highly experienced and strategic Director of Penetration Testing to lead our penetration testing department. This leadership role is responsible for overseeing all aspects of the team’s operations, strategy, and technical delivery. The ideal candidate will bring over 5 years of professional experience in penetration testing, including at least 3 years in a leadership or managerial role. The Director will be responsible for building and mentoring a high-performing team, developing testing methodologies, ensuring service excellence, and aligning the team's objectives with broader organizational goals.

KEY RESPONSIBILITIES

Strategic & Team Leadership

Lead and manage the penetration testing department, including hiring, mentoring, performance management, and resource planning

Define departmental goals and key performance indicators in alignment with company objectives

Establish and continuously improve testing methodologies, quality assurance standards, and operational workflows

Serve as the primary point of contact for executive leadership on penetration testing matters

Technical Leadership & Execution

Oversee and participate in complex penetration tests on enterprise networks, systems, applications, and cloud environments

Lead red team engagements, social engineering campaigns, and simulated real-world attacks

Ensure technical accuracy and completeness of all team deliverables and reports

Stay up to date with evolving threat landscapes, attack vectors, and security technologies to continuously innovate service offerings

Stakeholder Communication

Deliver clear, impactful reports and presentations for both technical teams and executive stakeholders

Translate findings into actionable recommendations and risk mitigation strategies

Collaborate with IT, GRC, SOC, and security operations teams to guide remediation efforts

Compliance & Risk

Ensure the team's activities align with industry standards and regulatory frameworks such as PCI-DSS, HIPAA, and NIST

Develop, maintain, and enforce penetration testing policies and procedures

REQUIREMENTS

Education & Experience

Bachelor’s degree in Cybersecurity, Computer Science, Information Technology, or a related field

At least 5 years of hands-on penetration testing experience, including web, network, social engineering, and red team assessments

Minimum 3 years of experience managing or leading technical teams in a cybersecurity context

Proven track record of successfully delivering enterprise-level security testing projects

Experience with exploit development and advanced attack simulation is a plus

Certifications (Required or Strongly Preferred)

OSCP (required)

OSCE, OSWE, OSEP, or similar advanced certifications (preferred)

TECHNICAL SKILLS

Expert-level knowledge of penetration testing tools (e.g., Metasploit, Burp Suite, OWASP ZAP, Cobalt Strike)

Deep understanding of network protocols, operating systems (Windows, Linux), and cloud infrastructure (AWS, Azure, GCP)

Strong command of scripting and programming (Python, Bash, PowerShell, etc.)

Experience with risk analysis and vulnerability management

Exceptional written and verbal communication skills, including the ability to write detailed technical reports for diverse audiences

OTHER REQUIREMENTS

U.S. Citizenship or eligibility to obtain necessary security clearances (if applicable)

Ability to travel up to 25% if needed

Demonstrated leadership, strategic thinking, and ability to operate in a fast-paced environment

High level of integrity and discretion when handling sensitive information

Benefits
- Competitive Salary
- Flexible Paid Time Off and paid holidays
- Performance Bonuses
- Flexible remote work environment
- Opportunities for professional development and growth
- Supportive team culture

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