Freelance Penetration Tester Jobs (NOW HIRING)

Squadmakers is a leading technology staffing and consulting firm based in New York City. We specialize in providing top-quality professionals to our clients in various industries including finance, healthcare, and technology. We are committed to delivering innovative and efficient solutions to our clients' business needs.

Job Description:

We are seeking a Cybersecurity & Penetration Testing Specialist to ensure the security and resilience of our infrastructure and the solutions deployed for our clients. This role focuses on proactively identifying vulnerabilities, performing security assessments, and ensuring compliance with international data protection regulations.

Key Responsibilities: Infrastructure Security

Assess and secure customer's cloud infrastructure and platform environments.

Identify security risks in infrastructure architecture and propose remediation strategies.

Ensure systems are resilient against cyberattacks, unauthorized access, and service disruption.

Penetration Testing & Security Assessments

Perform regular penetration tests on internal systems, cloud environments, and client-facing applications.

Conduct vulnerability assessments and security audits.

Application Security Analysis

Analyze the security of web and API-based applications.

Identify vulnerabilities such as those defined in the OWASP Top 10.

Work with development teams to remediate security issues and improve secure coding practices.

Threat Prevention & System Resilience

Evaluate system defenses against hacking attempts, intrusion attacks, and exploitation techniques.

Recommend security improvements to increase platform resilience and incident response readiness.

Support the implementation of monitoring and detection mechanisms.

Compliance & Data Protection

Ensure compliance with GDPR and international data protection regulations.

Verify that ApolloV2 systems and client solutions comply with European and US security and privacy standards.

Conduct security reviews of systems handling sensitive athlete and medical data.

Security Documentation & Reporting

Produce detailed reports from penetration tests and vulnerability analyses.

Maintain documentation on security practices, controls, and remediation processes.

Provide security recommendations to technical and management teams.

Qualifications:

• Bachelor's degree in Computer Science, Information Technology, or a related field
• Minimum of 3 years of experience in a cybersecurity role
• Strong knowledge of cybersecurity principles, protocols, and technologies
• Experience with network and system security, intrusion detection, and vulnerability management
• Familiarity with industry compliance standards such as HIPAA, PCI, and GDPR
• Certifications such as OSCP, CEH, CISSP, or similar
• Experience performing red team / ethical hacking engagements
• Background in securing SaaS platforms
• Experience working with high-sensitivity data environments

Security Expertise

Penetration testing methodologies

Vulnerability assessment and risk analysis

Web application and API security

Network security fundamentals

Security architecture and infrastructure hardening

Security Standards & Frameworks

Experience working with or auditing against:

GDPR

SOC 2

ISO 27001

Data protection and privacy frameworks in the EU and US

Tools & Technologies

Experience with tools such as:

Penetration testing tools (Burp Suite, Metasploit, Nmap, OWASP ZAP)

Vulnerability scanners (Nessus, Qualys)

Network monitoring and logging tools

Security testing frameworks

Experience securing environments in:

AWS, Azure, or Google Cloud

Containerized environments (Docker, Kubernetes) is a plus

Programming / Technical Skills

Scripting or automation in Python, Bash, or similar

Ability to analyze and understand application codebases and system architecture

- Relevant certifications such as CISSP, CISM, or CEH are a plus

Location:

This is a freelance position based in remote, working with some of our customers (Europe and US).

This is a freelance position with the potential for long-term contract opportunities. The rate will be competitive and based on experience and qualifications.

If you are a dedicated and experienced Cybersecurity Engineer looking for a challenging and rewarding opportunity, we encourage you to apply to join our team at Squadmakers. We value diversity and are an equal opportunity employer.