Senior Penetration Test Lead — Remote Engagements

HeadHR; Town of Poland (NY); On-site; USD 120,000 - 150,000; Full time

Benefits offered by this job

Remote work

Job summary

HeadHR is seeking a senior penetration tester to lead offensive security engagements across web, network, mobile, and AD environments. You will own scoping, quality, reporting, and client relationships while coaching consultants and analysts.

The role requires 5+ years of hands-on testing, deep experience across multiple domains, and strong writing and presentation skills for technical and non-technical audiences. Remote delivery with potential on-site support will apply.

Qualifications

• 5+ years of hands-on penetration testing experience, including consultancy or multi-client delivery.
• Demonstrable depth across at least three: web, network, mobile, and AD testing.
• Strong command of industry-standard tooling (Burp Suite, Nmap, Metasploit, Cobalt Strike or equivalent).
• Solid networking and OS internals knowledge (Windows/Linux).
• Scripting/automation in Python, PowerShell, or Bash.
• Excellent report writing and ability to explain risk to non-technical audiences.
• Experience managing client relationships and leading small delivery teams.

Responsibilities

• Manage engagements from initiation through reporting and closure.
• Act as primary client contact during testing activities.
• Review and quality-assure findings and reports.
• Assist with scoping, estimation, and proposals.
• Present findings to technical and non-technical stakeholders.
• Contribute to methodology, tooling, and playbooks.
• Support business development with pre-sales input.
• Uphold delivery standards aligned to recognized frameworks.

Skills

Penetration testing

Offensive security

Client delivery

Report writing

Python/PowerShell

Burp Suite

Nmap

Cobalt Strike

Communication skills

Tools

Burp Suite

Nmap

Metasploit

BloodHound/SharpHound

Impacket

CrackMapExec/NetExec

Cobalt Strike

Nessus/OpenVAS

Frida/MobSF/objection

Job description

HeadHR is seeking a senior penetration tester to lead offensive security engagements across web, network, mobile, and AD environments. You will own scoping, quality, reporting, and client relationships while coaching consultants and analysts.

The role requires 5+ years of hands-on testing, deep experience across multiple domains, and strong writing and presentation skills for technical and non-technical audiences. Remote delivery with potential on-site support will apply.