Penetration Tester

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Workstreet

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2023

🔒 Cybersecurity

📋 Compliance

🤝 B2B

Cybersecurity • Compliance • B2B

Workstreet is a managed security and compliance services provider that helps businesses automate and modernize their security programs. With expertise in compliance frameworks including SOC 2, ISO 27001, HIPAA, and GDPR, Workstreet supports companies in achieving their security and compliance outcomes efficiently. Their services include acting as a virtual Chief Information Security Officer (vCISO), full-scale penetration testing, and vendor risk management, aiming to streamline security processes while allowing businesses to focus on growth.

📋 Description

• Execute comprehensive penetration tests across web, mobile, network, and system environments • Uncover, exploit, and validate critical infrastructure and application vulnerabilities • Produce technical reports documenting exploit impact and proof-of-concept chains • Translate complex risk metrics into actionable remediation roadmaps • Partner with client engineering teams on post-assessment remediation • Troubleshoot implementation blocks and verify 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 investigating compromise vectors and helping accelerate threat containment • Maintain transparent client communications and gather environmental prerequisites • Track the evolving threat landscape and update assessment playbooks with current exploit techniques and defensive countermeasures

🎯 Requirements

• Proven history executing structured penetration tests, vector mapping, and threat validation across application, network, and system environments • Experience with industry-standard testing platforms, exploitation architectures, and reporting frameworks • Experience exploiting, classifying, and cataloging multi-tier security vulnerabilities • Ability to produce high-fidelity assessment documentation, exploit-chain proofs, and detailed impact reports • Ability to communicate tactical risk scenarios and remediation expectations to technical teams and executive stakeholders • Experience engineering custom testing scripts, phishing simulations, and pretexting campaigns • Advanced local testing station optimized for heavy virtual machine deployment • Ability to work standard U.S. Eastern Time hours, 8:00 AM–5:00 PM ET • OSCP, CEH, or equivalent offensive security credential actively held or pursued • Experience with cloud infrastructure penetration testing, container security evaluations, or environment configuration audits in AWS, GCP, or Azure • Practical alignment of vulnerability data with SOC 2, GDPR, or HIPAA audit and evidence requirements • Experience scaling offensive security workflows in high-velocity startups • Experience supporting incident response containment or designing technical employee threat-awareness initiatives • Excellent written and verbal English communication skills • Reliable high-speed internet connection and professional home office environment • Willingness and ability to travel locally for occasional onsite meetings, team gatherings, or business activities • Participation in live video interviews with camera on and identity verification during recruitment and onboarding • Successful identity verification and background screening, where permitted by law

🏖️ Benefits

• Career development with mentorship and training opportunities • Reimbursement for successful completion of approved role-related training and certification courses • Competitive base salary • Regular performance reviews linked to merit-based appraisals • Bonus opportunities • Significant room for career advancement • Remote-first flexibility • Opportunity to collaborate with a global team