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Role Description

The Lead Penetration Tester is an experienced offensive security professional who reports directly to the Director of Offensive Security. In this client-facing role, you will lead and execute penetration testing engagements for MSSP customers, serve as an escalation point for other penetration testers, and help ensure high-quality, defensible deliverables across the team.

• Lead and execute penetration tests primarily across web applications, external APIs, and networks, performing manual testing, exploitation, and validation beyond automated scanning.
• Serve as the primary escalation point for other penetration testers to unblock investigations, validate exploitation paths, and review findings for accuracy and consistency.
• Conduct scoping calls with customers, confirm rules of engagement, and manage the pentest lifecycle.
• Present findings to engineering teams and executive stakeholders, translating technical issues into remediation priorities.
• Contribute to internal offensive security tooling, playbooks, templates, and scripts.

Qualifications

• Minimum 2 years of verifiable experience as a professional penetration tester in a full-time role.
• Direct experience in pentesting web applications, external web APIs, and networks.
• Experience in one or more of the following categories:
  • Mobile Applications
  • Cloud Infrastructures (AWS, Azure, GCP)
  • GenAI/ML
  • Desktop (Thick Client) Applications
  • Vishing/Phishing
  • Secure Code Reviews
• Strong exploitation and validation skills with technical abilities above verifying scan results.
• Ability to produce clear and precise penetration test reports with reproducible steps and screenshots of evidence to provide practical remediation guidance effectively with customers.
• Ability to mentor and uplift other Offensive Security team members through technical guidance, review, and structured feedback.
• Must be currently based in the United States. No sponsorship available for this position.

Benefits

• Supportive leadership and a clear growth path
• 100% of employee medical premiums are covered by the employer and discounted family insurance options
• Dental and Vision Benefits
• PTO and Sick Time + 11 paid Holidays
• 401K retirement option with company match
• Company-paid Life Insurance
• Annual Subscription to TalkSpace (online counseling & therapy service)