Penetration Tester

About Workstreet

At Workstreet, we are 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 GRC (governance, risk, and compliance) services that support frameworks across SOC 2, ISO 27001, GDPR, CMMC, NIST 800-171, NIST 800-53, and FedRAMP.

Get to Know the Security Services Team

Our team spans three core functions: Cloud Security Engineering, Penetration Testing, and Vulnerability Management. We do not hide behind process or just point out gaps. We step in, build solutions, and deliver real security posture improvements with minimal disruption.

The Opportunity

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.

What You'll Do

• Execute comprehensive penetration tests across web, mobile, network, and system environments.
• Produce high-fidelity technical reports mapping exploit impact and proof-of-concept chains, with actionable remediation roadmaps for clients.
• Partner directly with client engineering teams to guide remediation and verify the integrity of deployed fixes.
• Engineer custom testing scripts, automation tools, and offensive methodologies.
• Deploy social engineering simulations, including targeted phishing and pretexting campaigns.
• Support incident response by providing offensive technical expertise and investigating compromise vectors.
• Own the client experience through transparent communication and clear, business-friendly milestones.
• Track the evolving threat landscape and integrate new exploit techniques into assessment playbooks.

Who You Are

• Active offensive security operator with a proven history of structured penetration tests and threat validation.
• Master of offensive frameworks, exploitation architectures, and reporting frameworks.
• Surgical exploit and validation engineer who catalogs multi-tier vulnerabilities and validates fixes.
• Precision technical author who produces high-fidelity assessment documentation.
• High-impact security diplomat who communicates risk to technical and executive stakeholders.
• Social engineering and automation developer.
• Autonomous remote operator working standard US Eastern Time hours.
• Validated offensive security specialist holding or pursuing OSCP, CEH, or equivalent credentials.

What Helps You Succeed

• Advanced cloud security auditing within AWS, GCP, or Azure.
• Integration of GRC compliance frameworks such as SOC 2, GDPR, or HIPAA.
• Experience in high-velocity startups.
• Incident containment and threat awareness training.

What We Offer

• Career development with mentorship and training opportunities.
• Reimbursement for approved training and certification courses.
• Competitive base salary with performance reviews and bonus opportunities.
• Growth opportunity in an early-stage company.
• Remote-first culture with flexibility to work from anywhere.

What You'll Need to Thrive

• Excellent written and verbal English communication skills.
• A reliable, high-speed internet connection and a professional home office environment.
• Commitment to a standard schedule of 8:00 AM to 5:00 PM U.S. Eastern Time.
• Willingness to travel locally for occasional onsite meetings.

Hiring and Selection Process

• Candidates must participate in live video interviews with camera on and verify identity during recruitment and onboarding.
• Employment is contingent upon successful identity verification and background screening, where permitted by law.
• Selected candidates will participate in structured interviews with hiring managers and cross-functional stakeholders.
• Candidates will receive prompt updates throughout the interview process.

Equal Opportunity Employer

Workstreet is an equal opportunity employer committed to providing employment opportunities to all individuals 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.