
Manager, Offensive Cybersecurity – Penetration Testing
Posted 1 day ago

Posted 1 day ago
This is a fully remote position, open to applicants in California.
• Lead and manage penetration testing initiatives across enterprise applications, systems, networks, cloud platforms, and other relevant environments.
• Determine testing scope, methodology, and priorities informed by business risk, threat intelligence, and organizational goals.
• Validate vulnerabilities and attack pathways through manual testing, proof-of-concept creation, and adversary emulation techniques.
• Collaborate with engineering, infrastructure, and application teams to share findings, support remediation efforts, and enhance overall security posture.
• Guide, mentor, and develop team members to bolster offensive security capabilities and technical expertise.
• Establish and refine offensive security processes, methodologies, reporting standards, and quality controls.
• Create metrics and reporting systems to convey testing coverage, trends in findings, remediation progress, and program effectiveness to leadership.
• Work with cross-functional stakeholders to prioritize testing tasks and facilitate secure design and corrective actions.
• Develop or modify proof-of-concept exploits to confirm vulnerabilities and evaluate potential business impacts.
• Construct repeatable assessment and reporting processes that comply with audit, compliance, and governance requirements.
• Bachelor’s degree in Computer Science, Information Security, or a related field, or equivalent professional experience; advanced degree is preferred.
• OSCP, OSEP, CRTP, CEH, CPT, CEPT, GPEN, or other recognized industry-standard penetration testing certifications are required.
• Over 7 years of combined IT and security experience with a wide-ranging exposure to systems analysis, application development, database design, networking, administration, identity, or other relevant responsibilities is preferred.
• Minimum of 5 years of experience in information security is required.
• At least 3 years of experience conducting penetration testing is required.
• Ability to work independently and resolve technical and business process-related issues effectively.
• Develop expert-level knowledge in the entire information security stack.
• Create technical testing solutions for internal use.
• Capable of accurately analyzing and scoping vulnerability disclosures and CVEs.
• Proficiency in OWASP.
• Experience in leading penetration testing programs or engagements within a large enterprise setting.
• Strong understanding of threat vectors and containment strategies.
• Familiarity with Active Directory discovery, enumeration, and exploitation methods.
• Experience assessing cloud environments (AWS, Azure, GCP), including common misconfigurations, attack pathways, and defensive measures.
• Exceptional written and verbal communication skills, with the ability to present technical findings to both technical and non-technical audiences.
• Group health insurance benefits (medical, vision, dental).
• FSA and HSA healthcare accounts.
• Life and accident insurance.
• Adoption and fertility assistance.
• Paid parental leave of up to 6 weeks.
• Short/long term disability coverage.
• Paid time off for vacation, personal needs, and sick time.
• Up to 17 days of Choice Time Off (CTO) per calendar year.
• Up to 11 paid holidays per calendar year.
• Opportunity to contribute to a 401(k) savings and investment plan with employer matching.
Weekday (YC W21)
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