Manager – Offensive Cybersecurity, Penetration Testing

Robert Half

. Lead and oversee penetration testing engagements across enterprise applications, systems, networks, cloud platforms, and other in-scope environments .

Posted 9/21/2026full-timeRemote • California • United StatesMid-LevelSenior💰 $123,000 - $190,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in penetration testing methodologies, vulnerability assessment, and security program leadership. Proficient in developing technical solutions and communicating findings to diverse stakeholders while enhancing organizational security posture.

Highest-signal resume keywords

Penetration TestingVulnerability AssessmentInformation Security CertificationsCloud Security AssessmentThreat Intelligence

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Penetration TestingVulnerability ManagementApplication SecurityNetwork SecurityThreat Vector AnalysisTechnical Testing SolutionsCVE AnalysisSecurity Tooling ExpertiseScripting LanguagesActive Directory Exploitation

Soft Skills

Excellent Communication SkillsTeam LeadershipMentoringIndependent Problem Solving

Tools & Technologies

MetasploitBurp SuiteKali LinuxEndpoint Detection and ResponseAWSAzureGCP

Certifications & Qualifications

OSCPOSEPCRTPCEHCPTCEPTGPEN

Industry Keywords

Offensive SecurityThreat IntelligenceSecurity PostureComplianceGovernanceAudit

Tech Stack

Tools & technologies

AWSAzureCloudGoogle Cloud PlatformLinuxPythonC++

About the role

Key responsibilities & impact

Lead and oversee penetration testing engagements across enterprise applications, systems, networks, cloud platforms, and other in-scope environments
Define testing scope, methodology, and priorities based on business risk, threat intelligence, and organizational objectives
Validate vulnerabilities and attack paths through manual testing, proof-of-concept development, and adversary emulation techniques
Partner with engineering, infrastructure, and application teams to communicate findings, support remediation, and improve overall security posture
Lead, mentor, and develop team members to strengthen offensive security capabilities and technical depth
Establish and mature offensive security processes, methodologies, reporting standards, and quality controls
Develop metrics and reporting to communicate testing coverage, findings trends, remediation progress, and program effectiveness to leadership
Collaborate with cross-functional stakeholders to prioritize testing activities and support secure design and remediation efforts
Develop or adapt proof-of-concept exploits to validate vulnerabilities and assess potential business impact
Create repeatable assessment and reporting processes supporting audit, compliance, and governance requirements

Requirements

What you’ll need

Bachelor’s degree in Computer Science, Information Security, or a related field, or equivalent practical experience
OSCP, OSEP, CRTP, CEH, CPT, CEPT, GPEN or other experienced industry standard penetration testing certification(s) required
7+ years of combined IT and security work experience with broad exposure to systems analysis, application development, database design, networking, administration, identity, or other responsibilities preferred
5+ years’ experience in information security required
3+ years’ experience performing penetration testing required
Ability to work independently and troubleshoot technical and business process related issues
Subject matter expertise in the entire information security stack
Ability to develop technical testing solutions for internal consumption
Ability to analyze and scope vulnerability disclosures and CVEs
Expertise in OWASP
Experience leading penetration testing programs or engagements in a large enterprise environment
Excellent understanding of threat vectors and containment methods
Knowledge of Active Directory discovery, enumeration and exploit methods
Experience assessing cloud environments (AWS, Azure, GCP), including common misconfigurations, attack paths, and defensive controls
Excellent written and verbal communication skills, with ability to present technical findings to technical and non-technical audiences
Experience with multiple and current Endpoint Detection and Response solutions
Experience with Vulnerability Management concepts and best practices
Knowledge of Windows, Linux, Mac OS, and mobile operating systems
Expertise in networking concepts, protocols and encryption
Expertise in application security practices and tools
Expertise in programming/scripting languages such as Python, PowerShell, Bash, C/C++/C#
Expertise in Metasploit or similar tooling
Expertise in penetration testing security tooling such as Kali Linux
Expertise in Burp Suite or similar tooling
Purple team experience

Benefits

Comp & perks

Discretionary annual bonus
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
Paid time off for vacation, personal needs, and sick time
Up to 17 days of Choice Time Off (CTO) per calendar year for new hires
Up to 11 paid holidays per calendar year
401(k) savings and investment plan or deferred compensation plan (if eligible)
Employer match of 100% on the first 3% of contributions for eligible employees
Reasonable accommodation assistance for applicants with disabilities