Senior Cybersecurity Penetration Tester

Job Title: Sr. Cybersecurity Penetration Tester

Primary Location: 100% Remote

Position Type: Direct Hire

Must BE US Citizen and Green Card

Overview

A Sr. Cybersecurity Penetration Tester. This is a direct hire, fully remote role. The reason this position exists is to design, execute, and mature an enterprise adversarial testing and red team program that proactively identifies vulnerabilities across network, application, cloud, and infrastructure environments. This role plays a critical part in communicating security risk to technical and executive stakeholders while shaping long-term remediation strategies and the future growth of the penetration testing function.

What You Bring to the Role (Ideal Experience)

• Bachelor's degree in Information Security, Computer Science, Information Technology, or a related field; Master's degree preferred

• 5+ years of hands-on penetration testing or red team experience

• Experience building, expanding, or maturing a penetration testing or adversarial testing program

• Strong understanding of healthcare security standards and frameworks, including HIPAA and NIST

• Academic medical center or healthcare consulting experience strongly preferred

• Strong written and verbal communication skills with the ability to clearly articulate risk to technical and executive audiences

• Relevant certifications such as CEH, Pentest+, GPEN, and/or OSCP preferred

What You'll Do (Skills Used in this Position)

• Research, plan, and execute comprehensive penetration testing and red team operations across network, application, cloud, and infrastructure environments (40%)

• Identify and validate security vulnerabilities, exploits, and weaknesses in security controls

• Develop and maintain adversarial testing methodologies, playbooks, and procedures (20%)

• Conduct manual and automated network and security architecture reviews and advise on best practices (15%)

• Partner with IT and security teams to develop remediation recommendations and mitigation strategies (10%)

• Communicate findings, risks, and recommendations to IT leaders, engineers, and business stakeholders (10%)

• Support the growth and maturity of the penetration testing program, including mentoring and leading future team members

• Stay current on emerging threats, attack techniques, and industry best practices

• Perform other duties as assigned (5%)