Mid-Level Penetration Tester

Dragonfli Group is a cybersecurity and IT consulting firm providing services to federal agencies and Fortune 100 enterprises. Headquartered in Washington, DC, Dragonfli supports clients in securing mission-critical systems across on-site, hybrid, and fully remote environments.

Dragonfli Group is seeking a Mid-Level Penetration Tester to join a consolidated enterprise Penetration Testing program supporting a large federal agency. In this fully remote role, you will plan and execute authorized penetration tests across network, endpoint, wireless, database, application, and infrastructure environments, following structured Planning, Discovery, Testing, and Reporting phases. You will develop Rules of Engagement, Execution Plans, and decision-ready reporting, coordinate directly with system owners and SOC personnel to confirm scope and safety thresholds, and validate exploitable conditions arising from misconfigurations, outdated software, and weak access controls. You will also support validation of CISA WAS and FAST findings, KEV exposure items, and coordinate retesting to confirm closure, using approved AI-enabled tools to improve reconnaissance and ATT&CK/ATLAS mapping while maintaining human oversight. This role calls for approximately 5 to 8 years of relevant experience leading or independently executing penetration testing engagements.

This is a multi-year contract position involving a large US federal agency. Candidates with previous federal contracting experience are preferred. U.S. Citizenship or Permanent Residency is required. If hired, all work related to this role must be performed within the continental U.S.

This is a fully remote position.

Key Responsibilities:

• Plan and execute authorized penetration tests across network, endpoint, wireless, database, application, and infrastructure environments using structured Planning, Discovery, Testing, and Reporting phases.
• Develop and tailor Rules of Engagement, Execution Plans, daily status updates, and final reporting inputs for assigned assessments.
• Coordinate with system owners, SOC personnel, and other stakeholders to confirm 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• Validate vulnerabilities arising from misconfigurations, outdated software, weak access controls, incomplete control implementation, and exploitable attack paths.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, and 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.

Requirements

Must-Have

• 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

Preferred / Nice-to-Have

• Previous federal contracting experience
• Experience with CISA WAS, CISA FAST, and KEV validation and retest workflows
• Familiarity with MITRE ATT&CK and ATLAS mapping
• Advanced certifications such as OSCP, OSCE, GPEN, or GXPN
• Experience integrating AI-enabled tools into testing workflows while maintaining human oversight of results

Skill(s)

Technical Skills

• End-to-end penetration testing across network, endpoint, wireless, database, application, and infrastructure environments
• Rules of Engagement and Execution Plan development
• Vulnerability validation and exploit chain analysis
• CISA WAS/FAST and KEV validation and retesting
• MITRE ATT&CK/ATLAS mapping and AI-enabled testing tools

Soft Skills

• Stakeholder coordination with system owners and SOC teams
• Clear, decision-ready written and verbal reporting
• Sound judgment around safety thresholds and stop/pause procedures
• Ability to lead an assessment independently with minimal oversight
• Mentorship of junior testing staff

Benefits

• Dragonfli Group offers a comprehensive benefits package that includes:
• 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), 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
• PTO, 15 to 25 days annually based on tenure
• Paid Federal Holidays, All 11 federal holidays observed

Travel