Senior Red Team Lead & Penetration Tester (Remote)

Hampton North; Orlando (FL); Remote; USD 160,000 - 175,000; Full time

Job summary

Hampton North is seeking a Cybersecurity Engineer Principal to lead hands-on penetration testing and red team engagements across networks, apps, cloud, and identity systems. This senior role owns engagements end to end—from scoping and rules of engagement to reporting and remediation validation.

You start as an individual contributor and grow to lead the assessment team. Remote with onsite work in Orlando, FL, and Top Secret with SCI eligibility clearance are required.

Qualifications

• 10+ years in cybersecurity with hands-on pentesting and red team leadership.
• Top Secret clearance with SCI eligibility (no polygraph required).
• Bachelor’s degree in cybersecurity, computer science, IT, or related field, or equivalent experience.
• Hands-on testing across network, web app, API, cloud, identity, and wireless.
• Deep knowledge of Windows, Linux, Active Directory, networking protocols, authentication, and access controls.
• Cloud and hybrid environment assessments.
• Scripting in Python, PowerShell, and Bash.
• Experience with red team tooling and testing methodologies.

Responsibilities

• Lead penetration tests and red team operations across networks, web applications, APIs, cloud platforms, identity systems, and wireless.
• Scope engagements, set rules of engagement, and estimate level of effort, staffing, and delivery timelines.
• Build realistic attack scenarios, validate vulnerabilities, and demonstrate attack paths and business impact within approved boundaries.
• Run blue and purple team assessments alongside client and internal defenders to measure control effectiveness, detection coverage, and response, then drive practical improvements.
• Build and maintain red team infrastructure, custom tooling, scripts, and testing methodology.
• Write and review evidence-backed reports, elevate critical findings in real time, and brief both technical teams and executives.
• Mentor operators, support hiring, and grow into managing the assessment team.
• Provide periodic surge support on government engagements requiring TS/SCI.

Skills

Penetration testing

Red team leadership

Blue team coordination

Cloud platforms

Windows/Linux

Active Directory

Scripting (Python)

PowerShell

Education

Bachelor’s degree in cybersecurity, computer science, IT, or related field

Tools

Python

PowerShell

Bash

Red team tooling

MITRE ATT&CK tooling

Job description

Hampton North is seeking a Cybersecurity Engineer Principal to lead hands-on penetration testing and red team engagements across networks, apps, cloud, and identity systems. This senior role owns engagements end to end—from scoping and rules of engagement to reporting and remediation validation.

You start as an individual contributor and grow to lead the assessment team. Remote with onsite work in Orlando, FL, and Top Secret with SCI eligibility clearance are required.