Penetration Tester Team Lead (Red Team) - Executive Operations

We are seeking a highly skilled Penetration Tester Team Lead to oversee Red Team operations and simulate real-world cyberattacks across our systems, networks, and applications. You will lead a team of penetration testers and security engineers, execute advanced threat simulations, and collaborate closely with Blue Teams to harden our defenses.

This role involves hands-on engagement with offensive tools (Kali Linux, Metasploit, Burp Suite, Cobalt Strike), creating custom exploits, guiding junior testers, and providing strategic insights to improve our security posture.

Responsibilities:

• Lead Red Team exercises, threat simulations, and penetration tests

• Mentor a team of ethical hackers and engineers

• Perform advanced adversary emulation (phishing, social engineering, etc.)

• Collaborate with Blue Team to evaluate detection capabilities

• Report findings with actionable remediation strategies

• Develop custom offensive tools and scripts

• Research latest vulnerabilities and APT tactics

• Support development of overall cybersecurity strategy

• Educate internal teams on security threats and mitigation

📌 Requirements

• • Bachelor’s degree or equivalent in Cybersecurity, CS, or related

  • 5+ years in Pen Testing, Red Teaming, or Offensive Security

  • 2+ years in a leadership/mentorship role

  • OSCP, CEH, GPEN, OSWE or equivalent certifications

  • Deep experience with attack vectors, simulation tools, and threat modeling

  • Solid scripting skills (Python, Bash, PowerShell, JS)

  • Familiarity with MITRE ATT&CK, cloud (AWS, Azure), containers, and network exploitation

  • Excellent written and verbal communication
    Schedule: Monday–Friday, 9:00 AM – 5:00 PM EST
    

💰 Compensation

5-9/hour
Equivalent to $800-$1440/month (Full-time, 40 hrs/week)
Based on experience and final alignment