Sr. Penetration Tester

HAMPTON NORTH LLC

Orlando, FL, United States

2 days ago

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Role details

Contract type

Permanent contract

Employment type

Full-time (> 32 hours)

Experience level

Expert

Experience required

10 years minimum

Compensation

$160,000.0 - $175,000.0

Working hours

Regular working hours

Job source

www.clearancejobs.com

Tech stack

Active Directory Application Programming Interfaces (APIs) Software System Penetration Testing User Authentication Bash Shell Cloud Computing Linux Intrusion Detection and Prevention Python (Programming Language) Network Protocols Open Web Application Security Windows PowerShell

+7 more

Red Team (Cyber Security) Web Applications Scripting Software Security Mitre Att&ck Information Technology Purple Team (Cyber Security)

Job description

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, escalate critical findings in real time, and brief both technical teams and executives
Validate client remediation after fixes land
Mentor operators, support hiring, and grow into managing the assessment team
Provide periodic surge support on government engagements requiring TS/SCI

Requirements

10+ years in cybersecurity, including substantial hands-on penetration testing and demonstrated red team leadership
Top Secret clearance with SCI eligibility (no polygraph required)
Bachelor’s degree in cybersecurity, computer science, IT, or a related field, or equivalent experience
Hands-on testing across network, web application, API, cloud, identity, and wireless
Deep knowledge of Windows, Linux, Active Directory, networking protocols, authentication, and access controls
Cloud and hybrid environment assessments
Scripting and tool development in Python, PowerShell, and Bash
Building and maintaining red team infrastructure and assessment tooling
Working knowledge of the OWASP Testing Guide, MITRE ATT&CK, and established penetration testing methodologies
Partnering with defensive teams to test detection and response capabilities
Strong technical writing, client communication, and executive presentation skills
Ability to scope effort, manage competing engagement priorities, and deliver independently
Bonus points: OSCP, OSEP, OSWE, CRTO, CISSP, or CEH; master’s degree in a related field; consulting or boutique firm experience across concurrent clients; mixed commercial and government delivery; experience building an assessment practice or managing pentesters and red team operators
Bonus points: advanced depth in adversary emulation, application security, cloud exploitation, exploit development, or detection engineering

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