Description review
Mid-Level Penetration Tester
Dragonfli Group · United States · back to the listing
HR standards
62/100
needs work
Title ↔ description
94/100
strong
Reads as
Security Engineer
94% confident
What this role officially is
ICT security administrator — ESCO, the EU occupation classification
ICT security administrators plan and carry out security measures to protect information and data from unauthorised access, deliberate attack, theft and corruption.
Also known as: network security administrator, system security administrator, ICT security administrators, IT security administrator
How others title the same work
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What the listing never says
- 36 bullet points. Long requirement lists deter qualified candidates, who read them as hard gates. Scope clarity
- No pay range published. Candidates cannot tell whether applying is worth their time. Pay transparency
The listing, marked up
Nothing in the wording of this listing tripped a check. The scores above still judge how complete and coherent it is.
Description
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personnel to confirm scope and safety thresholds, and validate exploitable conditions arising from misconfigurations, outdated software, and weak access controls.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
Originally posted on Himalayas
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
Originally posted on Himalayas