Role & seniority: Sr. Cybersecurity Penetration Tester (Senior-level, lead/adversarial testing program growth)

Stack/tools: Fully remote penetration testing across network, application, cloud, and infrastructure; development of adversarial testing methodologies and playbooks; healthcare security standards (HIPAA, NIST); relevant certs (CEH, Pentest+, GPEN, OSCP)

Top 3 responsibilities

Plan and execute comprehensive penetration testing and red team operations across multiple environments
Identify/validate vulnerabilities; develop and maintain testing playbooks and methodologies
Present findings to IT leadership and engineers; mentor team members; collaborate on remediation and stay current on threats

Must-have skills

5+ years hands-on penetration testing or red team experience
Experience building or maturing pen-testing/adversarial programs
Knowledge of healthcare security standards (HIPAA, NIST) and ability to communicate to technical and executive audiences
Strong written/verbal communication; relevant certifications (CEH, Pentest+, GPEN, OSCP)

Nice-to-haves

Experience in academic medical centers or healthcare consulting
Master’s degree (Information Security, CS, IT, or related)
Location & work type: Remote; Direct Hire; U.S. work authorization required (no visa sponsorship)

Full Description

Job Title: Sr. Cybersecurity Penetration Tester

Location: Remote

Position Type: Direct Hire

Overview

We are seeking a Sr. Cybersecurity Penetration Tester to lead the design, execution, and growth of an enterprise adversarial testing and red team program. This fully remote, direct hire role is critical in identifying vulnerabilities across network, application, cloud, and infrastructure environments. You will communicate security risks effectively to both technical teams and executive leadership while shaping long-term remediation strategies.

Ideal Experience

Bachelor’s degree in Information Security, Computer Science, IT, or related field; Master’s preferred
5+ years of hands-on penetration testing or red team experience
Proven experience building or maturing penetration testing/adversarial testing programs
Strong knowledge of healthcare security standards and frameworks (HIPAA, NIST)
Experience in academic medical centers or healthcare consulting is highly preferred
Excellent written and verbal communication skills for technical and executive audiences
Relevant certifications such as CEH, Pentest+, GPEN, and/or OSCP preferred

Key Responsibilities

Plan and execute comprehensive penetration testing and red team operations across various environments (network, application, cloud, infrastructure)
Identify and validate security vulnerabilities and weaknesses
Develop and maintain adversarial testing methodologies and playbooks
Conduct manual and automated security architecture reviews and advise on best practices
Collaborate with IT and security teams to recommend remediation and mitigation strategies
Present findings and risks to IT leaders, engineers, and business stakeholders
Mentor and lead future team members to grow the penetration testing program
Stay updated on emerging threats, attack techniques, and industry best practices

Compensation

Salary range is $140,000–$160,000 annually, based on experience and qualifications. Benefits include health insurance, 401(k), and paid time off. This role requires U.S. work authorization without visa sponsorship.

Additional Info

All offers are contingent upon background checks, including reference, education, employment verification, drug testing, and other compliance requirements.
Interested? Contact Lorie for more details and to apply.