Senior Penetration Testing Engineer: AI/LLM Security Lead

Jobtailor; Massachusetts; On-site; USD 120,000 - 160,000; Full time

Job summary

Jobtailor is seeking an experienced Penetration Tester to lead and execute comprehensive security assessments for web, API, and mobile apps, and manage third-party testing vendors. The role emphasizes delivering regulator-ready reports with remediation guidance and strengthening secure development practices.

Ideal candidates have 5+ years in testing across applications and networks, a track record of vendor management, and familiarity with AI/LLM-enabled testing techniques.

Qualifications

• 5+ years in penetration testing with strong experience across both application and network testing in high-security/highly regulated environments.

Responsibilities

• Design and manage third-party network penetration tests, including scoping, vendor selection, rules of engagement, quality assurance, and validation of results

Skills

Penetration Testing

Application Security

Network Security

Risk-Based Remediation

Vendor Management

Education

BS/MS in a relevant field

OSCP

OSEP

OSWE

GPEN

GXPN

GWAPT

PNPT

GCPN

Tools

AI/LLM Testing Techniques

Secure Development Practices

Quality Assurance

Job description

Jobtailor is seeking an experienced Penetration Tester to lead and execute comprehensive security assessments for web, API, and mobile apps, and manage third-party testing vendors. The role emphasizes delivering regulator-ready reports with remediation guidance and strengthening secure development practices.

Ideal candidates have 5+ years in testing across applications and networks, a track record of vendor management, and familiarity with AI/LLM-enabled testing techniques.