REMOTEFULLTIME
Penetration Tester

Workstreet
Remote · remote · Posted 2d ago
Sourced from
Undisclosed2–5 yrsfulltimeRemote
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Section · 01
About this role
The Opportunity
What you'll do
Who you are
What helps you succeed
Disclaimer: This job posting and Location has been aggregated from external source. Role details, content, and availability are subject to change. Applicants are advised to confirm the latest information directly on the company website before applying.
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 makes this team special isn't just our technical depth; it is how we back each other up. Our strongest engineers and assessors are the ones building reusable modules, writing custom tools, jumping into channels to unblock teammates, and mentoring without being asked. From early-stage startups to regulated enterprises, you will work directly with clients, take on real ownership early, and be surrounded by people who want to see you get good. If you enjoy solving tough security problems and want to be part of a team that is scrappy enough to move fast but seasoned enough to get it right, you will be in good company here.
What you'll do
- Execute comprehensive penetration tests across web, mobile, network, and system environments to uncover, exploit, and validate critical infrastructure and application vulnerabilities.
- Produce high-fidelity technical reports mapping out exploit impact and proof-of-concept chains, translating complex risk metrics into actionable remediation roadmaps for clients.
- Partner directly with client engineering teams to guide post-assessment remediation, troubleshoot implementation blocks, and systematically verify the integrity of deployed fixes.
- Engineer custom testing scripts, automation tools, and offensive methodologies to continuously expand vulnerability discovery coverage and testing precision.
- Deploy tactical social engineering simulations, including targeted phishing and pretexting campaigns, to rigorously audit human security awareness and organizational defenses.
- Support active incident response loops by providing offensive technical expertise, investigating compromise vectors, and accelerating threat containment pipelines.
- Own the supporting client experience by maintaining transparent communications, gathering environmental prerequisites, and breaking down testing footprints into clear, business-friendly milestones.
- Track the evolving threat landscape to continuously integrate cutting-edge exploit techniques, active vector changes, and defensive counter-measures into live assessment playbooks.
Who you are
- Active offensive security operator - Command a proven history of executing structured penetration tests, vector mapping, and threat validation across complex application, network, and system environments.
- Master of offensive frameworks - Deployed industry-standard testing platforms, exploitation architectures, and reporting frameworks to uncover hidden systemic security vulnerabilities.
- Surgical exploit and validation engineer - Exploited, classified, and cataloged multi-tier security vulnerabilities, providing clear remediation roadmaps to client engineering teams to securely validate system fixes.
- Precision technical author - Formulated high-fidelity assessment documentation, exploit chain proofs, and detailed impact reports that translate complex threat data into highly structured, actionable guidance.
- High-impact security diplomat - Articulated tactical risk scenarios, testing footprints, and remediation expectations with professional clarity to both deep technical infrastructure teams and executive client stakeholders.
- Social engineering and automation developer - Engineered custom testing scripts, targeted phishing simulations, and pretexting campaigns to audit human security awareness and expand overall assessment coverage.
- Autonomous remote operator - Command an advanced local testing station fully optimized for heavy virtual machine deployment, maintaining peak operational velocity during standard US Eastern Time working hours.
- Validated offensive security specialist - Hold or actively pursue high-value technical designations such as OSCP, CEH, or equivalent credentials that demonstrate a rigorous commitment to offensive security practices.
What helps you succeed
- Advanced cloud security auditing - Direct execution of cloud infrastructure penetration tests, container security evaluations, and environment configuration audits within AWS, GCP, or Azure.
- Integration of GRC compliance frameworks - Practical alignment of technical vulnerability data to satisfy the automated audit and evidence requirements of SOC 2, GDPR, or HIPAA.
Disclaimer: This job posting and Location has been aggregated from external source. Role details, content, and availability are subject to change. Applicants are advised to confirm the latest information directly on the company website before applying.
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Section · 02
Skills
AutomationBackground ScreeningAuditingAutomation ToolsEnglish Communicationgoogle cloud platformamazon web servicescehcontainer securityauditsclient deliveryCloud InfrastructureContainerdeploymentcloudCloud SecurityCyber SecuritycomplianceMicrosoft AzureArtificial Intelligence
Section · Company
About Workstreet

Workstreet
San Francisco
US
About
Workstreet provides AI-powered security and compliance automation solutions for modern tech and AI companies. Its services include virtual CISO, GRC, penetration testing, and security questionnaire automation. The company operates remotely with a global team and supports clients in accelerating their compliance and trust-building processes
Industries
Artificial Intelligence (AI)Online PortalsPenetration TestingSecurity
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