Penetration Tester

Job Description

Cybersecurity – Penetration Tester

Contract role, onsite, Midtown NYC

RedStream Technology is searching for a Penetration Tester / Ethical Hacker for their client’s Information Security team. The Penetration Tester is responsible for strengthening the client’s cyber security posture through manual and automated penetration testing, red team engagements, and offensive security assessments. The scope of the position's responsibilities includes planning and executing tests across applications, networks, and infrastructure to uncover exploitable vulnerabilities and attack paths that may be present within multiple environments.

Job Description/Key Responsibilities:

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• Plan and execute penetration tests across web applications, APIs, mobile apps, networks, cloud infrastructure (AWS/Azure/GCP), and internal systems
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• Perform manual exploitation and validation of vulnerabilities to eliminate false positives and uncover logic flaws automated tools miss
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• Design, configure, and run automated vulnerability scanning pipelines to accelerate coverage and consistency across engagements
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• Build and deploy AI-agent-driven testing workflows to accelerate reconnaissance, fuzzing, exploit chaining, and report generation
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• Ability to analyze the environment from a threat actor's perspective, including the skill to conduct prioritized identification of vulnerable assets, and then devise techniques to exploit potential attack paths
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• Identifies security risks, threats, misconfigurations and vulnerabilities of existing networks, systems, applications and develops solutions to remediate identified threats
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• Perform red team engagements simulating advanced persistent threat (APT) tactics, techniques, and procedures (TTPs)
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• Tracking and documenting testing activities and providing updates to leadership through executive summaries and in-depth technical reports
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• High performance skillset which not only understands the threat spaces as it relates to risks, but also able to meet the technical challenge of communicating this out to our client’s teams
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• 3+ years of direct experience performing penetration testing / red teaming in an active corporate environment
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• Experience consuming and analyzing Cyber Threat Intelligence for actionable takeaways
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• Experience explaining testing objectives and findings in plain English and able to communicate associated risk
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• Reporting gaps in a meaningful way that addresses a business risk as well as providing technical solutions to the operations teams in remediation is key
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Skills or experience required:

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• This is not a beginner level position and requires comfort and experience with manual security work, low level functionality, web application functionality, IT security, and vulnerability and threat management
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• Minimum 3 years of experience in the practice of penetration testing / ethical hacking
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• Technical Skills
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• Demonstrated experience planning and executing penetration test and red team engagements
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• Comfort operating in terminal environments
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• Ability to analyze an architectural document and strategically probe accordingly
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• Working knowledge of common ( DNS, SMB, etc.) networking protocols
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• Familiar with operation of both Windows and Linux based systems
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• Proficient with cross platform scripting languages such as Python or Golang, also PowerShell
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• Experience working with various technologies and platforms such as AWS, Azure, O365, GCP, containers, etc.
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• Proficiency with industry-standard testing tools such as Burp Suite, Metasploit, Nmap, Wireshark, Cobalt Strike, BloodHound, and the Kali Linux toolset
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• Practical experience integrating AI/LLM-based agents or copilots into security testing workflows (e.g., AI-assisted recon, automated exploit suggestion, agentic fuzzing frameworks) to accelerate results
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• Understanding of current cyber threat landscape, the different tactics commonly used by adversaries and how one would exploit, chain, and report against similar attack paths
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Desired Skills:

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• Strong work ethic with attention to detail
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• Demonstrated analytical abilities
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• Attention to detail, verbal and written communication, initiative, and motivation to learn
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• Strong written/oral communication skills required along with desire and ability to communicate with business leaders through all levels of the organization
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• Self-motivated with excellent planning and organizational skills; and the ability to prioritize tasks to meet deadlines and effectively manage changing priorities
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• Refined interpersonal skills with the ability to liaise confidently and professionally with a diverse range of people
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• Professional customer orientation with a strong commitment to providing a high standard of customer satisfaction
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• Ability to deliver client-ready documentation and participate in relevant client meetings
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• Working understanding of project management principles, processes, and documentation
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• Able to work across teams effectively and efficiently
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Preferred Education and Experience

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• Relevant industry standard certification(s) preferred: OSCP, other possibilities: OSCE, OSWE, GPEN, GXPN, CEH, CISSP
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• Bachelor's degree in information technology, Computer Science, Quality Assurance or equivalent
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