Penetration Tester Analyst

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 Pen Testing Analyst to join a growing Penetration Testing workstream supporting a large federal agency. In this fully remote role, you will provide analytical and hands-on support for authorized penetration testing activities, including test preparation, reconnaissance, evidence collection, documentation, and reporting for rapid validation efforts. You will help maintain test schedules and scope records, support controlled discovery and enumeration within approved authorization boundaries, and document findings and remediation recommendations for inclusion in final assessment reports. You will also assist with triage of external-facing asset findings, CISA WAS and FAST results, KEV exposure items, and Vulnerability Disclosure Program (VDP) submissions, and will use approved automation and AI-enabled tools to improve data collection, correlation, and reporting workflows. This role is well suited to a candidate with approximately 2 to 4 years of relevant experience in penetration testing, vulnerability assessment, or a closely related cybersecurity discipline.

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:

• Support assessment planning by maintaining test schedules, scope records, stakeholder coordination notes, and required pre-assessment documentation.
• Assist with controlled discovery, enumeration, testing support, and evidence capture within approved authorization boundaries.
• Document findings, affected assets, ownership, reproducibility details, remediation recommendations, and retest requirements for inclusion in final reports.
• Support validation and triage of external-facing asset findings, CISA WAS and FAST results, KEV exposure items, and VDP submissions.
• Coordinate daily status inputs, meeting notes, action tracking, and after-action support for assigned testing activities.
• Use approved automation and AI-enabled tools to improve data collection, initial correlation, draft reporting, and testing workflow efficiency.

Must-Have

• U.S. Citizenship or Permanent Residency (required for this federal engagement)
• Approximately 2 to 4 years of experience in penetration testing, vulnerability assessment, or a related offensive/defensive cybersecurity role
• Working knowledge of common penetration testing methodologies and tools (e.g., Burp Suite, Nmap, Metasploit, or equivalents)
• Familiarity with reconnaissance, enumeration, and evidence collection within authorized testing boundaries
• Strong written documentation skills for findings, reproducibility steps, and remediation recommendations
• Ability to work fully remote with reliable, secure connectivity

Preferred / Nice-to-Have

• Previous federal contracting experience
• Exposure to CISA Web Application Scanning (WAS) and Fast Attack Surface Testing (FAST) programs
• Familiarity with Known Exploited Vulnerabilities (KEV) catalog and Vulnerability Disclosure Program (VDP) triage
• Relevant certifications such as Security+, CEH, GPEN, or OSCP (or actively pursuing)
• Experience using AI-enabled or automation tools to support testing and reporting workflows

Technical Skills

• Penetration testing fundamentals and common toolsets
• Vulnerability scanning, enumeration, and evidence capture
• Report writing and findings documentation
• Familiarity with CISA WAS/FAST, KEV, and VDP processes
• Comfort with automation and AI-enabled testing support tools

Soft Skills

• Strong written and verbal communication
• Attention to detail and thorough documentation habits
• Ability to work independently in a remote, distributed team
• Collaborative coordination with stakeholders and testing leads
• Time management across concurrent assessment activities

• 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