Sr. Penetration Tester

Hampton North; Orlando (FL); À distance; USD 160 000 - 175 000; Plein temps

Résumé du poste

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.

Responsabilités

• 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.

Connaissances

Penetration testing

Red team leadership

Blue team coordination

Cloud platforms

Windows/Linux

Active Directory

Scripting (Python)

PowerShell

Formation

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

Outils

Python

PowerShell

Bash

Red team tooling

MITRE ATT&CK tooling

Description du poste

The Cybersecurity Engineer Principal is the senior penetration tester and red team lead for a boutique security assessment practice delivering red, blue, and purple team engagements to commercial and government clients. This is a hands-on technical lead seat that owns engagements end to end, from scoping and rules of engagement through testing, reporting, client briefings, and remediation validation. You start as an individual contributor reporting to the CEO, then recruit, develop, and lead the assessment team as it grows. Most of the work supports the commercial practice, with periodic surge support on cleared government engagements.

Target Compensation: $160,000 to $175,000 base

Logistics: Remote with onsite work in Orlando, FL, up to five business days per month - must be driving distance of Orlando

Clearance Required: Top Secret with SCI eligibility

Here’s what you’ll be doing:

• 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

And what you need to have:

• 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