Mid-Level Penetration Tester

Dragonfli Group

. Plan and execute authorized penetration tests across network, endpoint, wireless, database, application, and infrastructure environments .

Posted 9/15/2026full-timeRemote • United StatesMid-LevelSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in planning and executing penetration tests across various environments, including network, endpoint, wireless, database, application, and infrastructure. Proficient in developing Rules of Engagement and formal reporting while integrating AI-enabled tools into testing workflows.

Highest-signal resume keywords

Penetration TestingRules of Engagement DevelopmentCISA WAS ValidationMITRE ATT&CK FamiliarityAI-Enabled Tools Integration

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Penetration TestingVulnerability ValidationNetwork SecurityDatabase SecurityApplication SecurityInfrastructure SecurityExecution PlanningReportingReconnaissanceTesting Efficiency

Soft Skills

MentoringCollaborationCommunication

Tools & Technologies

Automated Testing ToolsAI-Enabled ToolsCISA FASTKEV Exposure Tools

Certifications & Qualifications

OSCPOSCEGPENGXPN

Industry Keywords

Federal ContractingSOC CoordinationSafety ThresholdsStop/Pause ProceduresExploitable Attack Paths

About the role

Key responsibilities & impact

Plan and execute authorized penetration tests across network, endpoint, wireless, database, application, and infrastructure environments
Follow structured Planning, Discovery, Testing, and Reporting phases
Develop and tailor Rules of Engagement, Execution Plans, daily status updates, and final reporting inputs
Coordinate with system owners, SOC personnel, and other stakeholders on scope, test windows, prerequisites, safety thresholds, and stop/pause procedures
Validate vulnerabilities arising from misconfigurations, outdated software, weak access controls, incomplete control implementation, and exploitable attack paths
Support validation of CISA WAS, CISA FAST, KEV exposure, and external-facing asset findings
Coordinate retesting to confirm closure
Use approved automated and AI-enabled tools to improve reconnaissance, testing efficiency, ATT&CK/ATLAS mapping, evidence development, and reporting while maintaining human oversight
Mentor junior testing staff
Independently lead assessments with minimal oversight

Requirements

What you’ll need

U.S. Citizenship or Permanent Residency required for this federal engagement
Approximately 5 to 8 years of experience conducting or leading penetration testing engagements
Demonstrated ability to plan and execute assessments across network, endpoint, wireless, database, application, and infrastructure environments
Experience developing Rules of Engagement, Execution Plans, and formal, decision-ready reporting for stakeholders
Experience coordinating directly with system owners and SOC personnel on scope, safety thresholds, and stop/pause procedures
Ability to work fully remote with reliable, secure connectivity
Previous federal contracting experience preferred
Experience with CISA WAS, CISA FAST, and KEV validation and retest workflows preferred
Familiarity with MITRE ATT&CK and ATLAS mapping preferred
Advanced certifications such as OSCP, OSCE, GPEN, or GXPN preferred
Experience integrating AI-enabled tools into testing workflows while maintaining human oversight of results preferred

Benefits

Comp & perks

Medical, multiple POS health plan options including an HSA-compatible plan
Dental, PPO coverage for preventive, basic, and major services
Vision, annual exam, frames, lenses, and contact lens allowance
401(k) with employer match up to 5% of eligible compensation
Long-Term Disability, 100% employer-paid coverage at 50% of pre-disability earnings
Life Insurance and AD&D, 100% employer-paid coverage valued at $10,000 each
15 to 25 PTO days annually based on tenure
All 11 federal holidays observed