Principal Penetration Tester / Offensive Security Team Lead

Role Overview: As the Principal Penetration Tester/ Offensive Security Team Lead, you will lead and scale the offensive security and penetration testing practice within a lean and fast-growing cybersecurity company. This player-coach role requires you to remain deeply hands-on, actively conducting penetration testing engagements while overseeing leadership, delivery, team mentorship, and business growth. Key Responsibilities: - Personally conduct and contribute to penetration testing engagements across various domains such as web applications, APIs, cloud environments, networks, mobile applications, wireless infrastructure, and enterprise systems. - Take ownership of complex, high-risk engagements requiring deep technical expertise. - Perform adversary simulation, exploit development, and advanced attack chain construction on client engagements. - Author and review high-quality technical reports with detailed findings, evidence, risk ratings, and actionable remediation guidance. - Stay current with offensive tooling, exploitation techniques, CVE research, and emerging attack vectors through personal practice and research. - Establish and evolve testing methodologies, quality standards, reporting frameworks, and operational best practices. - Ensure timely, high-quality delivery of client engagements while managing resource allocation and priorities. - Drive continuous improvement in offensive security capabilities, tooling, automation, and assessment approaches. - Lead internal research, proof-of-concept development, and red team innovation initiatives. Qualification Required: - Bachelor's degree in Computer Science, Information Security, Engineering, or related technical discipline, or equivalent experience. - 10+ years in cybersecurity focusing on hands-on penetration testing and offensive security. - Proven track record of personally executing penetration tests across multiple technology domains. - Experience leading or building penetration testing teams or offensive security practices. - Comfortable as an individual contributor on technical engagements while carrying leadership responsibilities. - Experience engaging directly with enterprise clients and executive stakeholders. - Prior experience in fast-paced, lean, or startup-oriented environments preferred. Additional Company Details: (Omitted as not present in the provided Job Description) Role Overview: As the Principal Penetration Tester/ Offensive Security Team Lead, you will lead and scale the offensive security and penetration testing practice within a lean and fast-growing cybersecurity company. This player-coach role requires you to remain deeply hands-on, actively conducting penetration testing engagements while overseeing leadership, delivery, team mentorship, and business growth. Key Responsibilities: - Personally conduct and contribute to penetration testing engagements across various domains such as web applications, APIs, cloud environments, networks, mobile applications, wireless infrastructure, and enterprise systems. - Take ownership of complex, high-risk engagements requiring deep technical expertise. - Perform adversary simulation, exploit development, and advanced attack chain construction on client engagements. - Author and review high-quality technical reports with detailed findings, evidence, risk ratings, and actionable remediation guidance. - Stay current with offensive tooling, exploitation techniques, CVE research, and emerging attack vectors through personal practice and research. - Establish and evolve testing methodologies, quality standards, reporting frameworks, and operational best practices. - Ensure timely, high-quality delivery of client engagements while managing resource allocation and priorities. - Drive continuous improvement in offensive security capabilities, tooling, automation, and assessment approaches. - Lead internal research, proof-of-concept development, and red team innovation initiatives. Qualification Required: - Bachelor's degree in Computer Science, Information Security, Engineering, or related technical discipline, or equivalent experience. - 10+ years in cybersecurity focusing on hands-on penetration testing and offensive security. - Proven track record of personally executing penetration tests across multiple technology domains. - Experience leading or building penetration testing teams or offensive security practices. - Comfortable as an individual contributor on technical engagements while carrying leadership responsibilities. - Experience engaging directly with enterprise clients and executive stakeholders. - Prior experience in fast-paced, lean, or startup-oriented environments preferred. Additional Company Details: (Omitted as not present in the provided Job Description)