Penetration Tester

At Workstreet, we’re on an exciting journey to help businesses scale securely by designing and implementing cutting-edge security and compliance programs. As a fast-growing startup, we specialize in a wide range of frameworks—including SOC 2, ISO 27001, GDPR, CMMC, NIST 800-171, NIST 800-53, and FedRAMP—empowering companies to meet regulatory requirements and enhance their cybersecurity posture from day one.

We are seeking a Penetration Tester to join our growing cybersecurity team. In this role, you will assess the security of applications, networks, and systems through structured penetration testing and vulnerability assessments. You will help identify weaknesses, document findings, and provide actionable recommendations to strengthen clients’ security defenses.

• Conduct Penetration Tests: Perform comprehensive security assessments across web, mobile, network, and system environments to uncover vulnerabilities.
• Identify and Document Vulnerabilities: Analyze findings, assess impact, and produce detailed reports with clear remediation recommendations.
• Collaborate on Remediation: Work with engineering and operations teams to validate fixes and strengthen overall system security.
• Execute Social Engineering Assessments: Test human security awareness through phishing, pretexting, and related simulations.
• Develop Testing Tools and Methods: Create and refine scripts, tools, and methodologies to enhance testing accuracy and coverage.
• Support Incident Response: Assist in investigations and provide technical expertise during threat containment and remediation.
• Stay Current with Threat Landscape: Continuously monitor emerging exploits, attack techniques, and best practices in offensive security.
• Contribute to Security Awareness: Participate in internal training and help improve organizational security policies and standards.

• Proven experience as a Penetration Tester or in a related cybersecurity testing role.
• Proficiency with penetration testing tools, methodologies, and reporting standards.
• Strong understanding of vulnerability identification, exploitation, and remediation processes.
• Excellent analytical, troubleshooting, and documentation skills.
• Effective communication skills with fluency in written and spoken English.
• Ownership of a capable workstation for running modern security testing tools.
• Amenable to working during US Eastern Time zone hours.
• Relevant certifications such as CEH, OSCP, or equivalent are preferred.

• Experience performing cloud security assessments in AWS, GCP, or Azure.
• Familiarity with compliance standards such as SOC 2, GDPR, or HIPAA.
• Experience working in a technology or cybersecurity startup environment.
• Exposure to security awareness or employee training initiatives.

• Career Development: Clear path with mentorship and training opportunities
• Technical Training: Comprehensive onboarding on security and compliance frameworks
• Competitive Compensation: A competitive base salary with regular performance reviews linked to merit-based appraisals and bonus opportunities.
• Growth Opportunity: Early-stage company with significant room for career advancement.
• Remote-First Culture: Flexibility to work from anywhere while collaborating with a global team.

• Reliable high-speed internet connection.
• Quiet, professional home office setup.
• Must be amenable to work US Eastern Time zone hours.
• Fluency in written and verbal English communication skills.

As an equal opportunity employer, Workstreet is committed to providing employment opportunities to all individuals. All applicants for positions at Workstreet will be treated without regard to race, color, ethnicity, religion, sex, gender, gender identity and expression, sexual orientation, national origin, disability, age, marital status, veteran status, pregnancy, or any other basis prohibited by applicable law.