Lead Penetration Tester

Location: Washington, DC, Ft. Collins, CO, or Kansas City, MO (project-based; onsite)

Terms: Full-time

Clearance: Active Secret required

Travel: Yes – travel to agency sites required

Project Description

This position leads operational security assessments and penetration testing across a portfolio of federal agencies and web applications. Assessments are conducted in accordance with the ISC Security Assessment Methodology and applicable federal rules of engagement, producing findings that reach agency CIO and CISO-level leadership. The program also requires FedRAMP-qualified penetration testing support for cloud service authorization activities.

The core challenge: leading a high-tempo assessment program across multiple agencies per year — each with distinct environments, rules of engagement, and stakeholder expectations — while producing deliverables that meet the evidentiary and presentation standards of senior federal leadership.

Position Description

As a Lead Penetration Tester at Revolutional, you own the end-to-end execution of operational security assessments and web application penetration tests across a federal agency portfolio. You develop test plans, lead technical execution, produce security assessment reports and criticality matrices, and deliver out-brief presentations directly to agency CIO and CISO-level audiences. You are the senior technical authority on every engagement you lead.

You bring deep experience with federal assessment methodologies — ISC Security Assessment Methodology, OWASP, NIST SP 800 series, and DISA STIG — and hold or are actively pursuing CISA AES certification. You are equally comfortable executing a technically complex assessment and standing in front of agency leadership to explain what you found and what it means.

What You Will Own

• Operational security assessment leadership across a portfolio of federal agencies (approximately 6–7 per year)
• Web application security assessments (approximately 3–4 applications per year)
• Test plan and rules of engagement development for each assessment
• Criticality matrix development and risk prioritization
• Security assessment report authorship and quality
• Out-brief presentations to agency CIO and CISO-level leadership
• FedRAMP penetration testing support for cloud service authorization

Responsibilities

• Lead operational security assessments across federal agencies in accordance with the ISC Security Assessment Methodology and applicable rules of engagement; manage approximately 6–7 agency assessments per year
• Conduct web application security assessments using OWASP methodology; assess approximately 3–4 applications per year across a range of agency environments
• Develop comprehensive test plans for each engagement: scope definition, assessment objectives, methodology selection, rules of engagement, and timeline
• Build criticality matrices that prioritize findings by risk, asset value, and mission impact to support agency remediation planning
• Author detailed security assessment reports documenting findings, evidence, risk ratings, and actionable remediation guidance meeting federal evidentiary and reporting standards
• Develop and deliver out-brief presentations to agency CIO, CISO, and senior leadership audiences; communicate complex technical findings with clarity and executive-level credibility
• Conduct FedRAMP-qualified penetration testing in support of cloud service authorization activities; apply FedRAMP pen testing requirements and documentation standards
• Apply NIST SP 800 series guidance and DISA STIG methodology throughout assessment planning, execution, and reporting
• Coordinate with agency stakeholders before, during, and after assessments to manage expectations, address questions, and ensure findings are understood and acted upon
• Stay current on vulnerability research, offensive techniques, and emerging attack surfaces relevant to federal civilian agency environments

What You Bring (Requirements)

Baseline Requirements

• Bachelor's degree in Computer Science, Information Security, or related field (or equivalent experience)
• 5 or more years of hands-on penetration testing experience, with demonstrated experience leading assessments in federal environments
• CISA AES (Authorized External Security) certification required, or actively in process of obtaining
• FedRAMP penetration testing experience required
• Active Secret clearance
• Ability and willingness to travel to agency sites as required

Technical & Domain Capabilities

• Deep experience conducting operational security assessments in accordance with the ISC Security Assessment Methodology and federal rules of engagement
• Proficiency with OWASP methodology applied to web application security assessments across federal environments
• Working knowledge of NIST SP 800 series guidance as applied to security assessment planning, execution, and reporting
• Experience applying DISA STIG methodology to assessment scope and findings documentation
• Experience developing test plans, criticality matrices, and security assessment reports that meet federal evidentiary and leadership reporting standards
• Demonstrated experience presenting technical security findings to CIO, CISO, and senior agency leadership audiences
• FedRAMP-qualified penetration testing experience, including familiarity with FedRAMP pen test requirements, documentation, and cloud authorization processes
• Proficiency with industry-standard penetration testing toolsets for network, application, and infrastructure assessments

Core Strengths

• Senior assessment lead: you own engagements end-to-end and your findings are technically sound, clearly documented, and risk-rated with precision
• Executive-ready communicator — you develop and deliver out-brief presentations that land with CIO and CISO audiences, not just technical teams
• Methodologically disciplined: you work within rules of engagement, document everything, and produce deliverables that hold up under agency and regulatory scrutiny
• High-tempo operator who manages multiple concurrent engagements across different agency environments without loss of quality or attention to detail

Certifications

The following certifications are required or strongly preferred:

Required

• CISA AES (Authorized External Security) Assessment Lead or Technical Lead certification (or actively in process)

Strongly Preferred

• GPEN (GIAC Penetration Tester), GXPN (GIAC Exploit Researcher and Advanced Penetration Tester), OSCP (Offensive Security Certified Professional), or equivalent offensive security credential
• GWAPT (GIAC Web Application Penetration Tester) or equivalent web application security certification

Nice to Have (Differentiators)

• Experience conducting CISA AES assessments as Assessment Lead across multiple federal civilian agencies
• Familiarity with FedRAMP High, Moderate, and Low authorization boundaries and their penetration testing implications
• Background in Red Team operations or adversary emulation in addition to structured assessment methodology
• Experience with cloud-native application security assessments (AWS, Azure, GCP, or GovCloud)
• Active TS/SCI clearance

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