Senior Penetration Tester (Cybersecurity)

TL;DR

Senior Penetration Tester (Cybersecurity): Serving as the Red Team technical lead for Offensive Security by conducting Red, Purple, and Application penetration tests with an accent on threat emulation and adversarial attack paths. Focus on designing custom offensive capabilities, managing C2 infrastructure, and mentoring junior security staff.

Location: Remote (USA) / Livonia, Michigan

Company

hirify.global is a large healthcare organization dedicated to delivering compassionate, person-centered care.

What you will do

• Lead Red Team engagements, application penetration tests, and Purple Team activities.
• Design threat scenarios and execute complex assessments across diverse infrastructures to enhance security posture.
• Develop and operate custom offensive capabilities and secure cloud-based C2 infrastructure.
• Conduct root cause analysis for security incidents and provide strategic remediation guidance.
• Mentor junior and mid-level penetration testers through technical workshops and guidance.
• Produce strategic risk reports and executive summaries for senior management.

Requirements

• Bachelor’s degree in Information Security, Computer Science, or equivalent professional experience.
• 6-8+ years of experience in penetration testing or red teaming with a track record of leading complex assessments.
• Deep expertise in Active Directory and Microsoft Entra ID architecture and attack paths.
• Advanced scripting skills in Python, C, or PowerShell for automating testing processes.
• Proficiency with ITSM tools like ServiceNow and Jira for workflow optimization.
• Must be based in the United States.

Nice to have

• Industry certifications such as OSCP, CRTO, eWPTX, OSEP, OSWE, OSED, or OSCE3.

Culture & Benefits

• Commitment to diversity, equity, and inclusion as an Equal Opportunity Employer.
• Focus on dignity, respect, and person-centered care values.
• Opportunities for continuous professional development to stay ahead of evolving threats.