Penetration Tester

Company Description Outcome School is a free tech school that offers structured, level-based programs in software engineering, AI, product, robotics, game development, and cybersecurity. Its pathways are designed to help underserved and minority youth build skills step by step through prerequisite-based training, with each level running for 12 weeks. The organization focuses on outcome-based learning that connects practical, technology-driven skills directly to workforce readiness and meaningful employment. Outcome School partners with employers to create hiring pathways and measurable employment and income outcomes for participants. Its mission is to equip learners with job-ready technical and professional skills that support long-term economic mobility through a scalable and repeatable program model.
Role Description This is a full-time remote role for a Penetration Tester at Outcome School. The Penetration Tester will be responsible for planning, executing, and documenting security assessments for web applications, networks, and cloud environments. Day-to-day tasks include performing vulnerability scans, manual exploitation, and red teaming exercises to evaluate the resilience of systems and applications. The role involves reverse engineering binaries, analyzing potential malware, and assessing application security controls to identify and validate security weaknesses. The Penetration Tester will collaborate with engineering, cybersecurity, and curriculum teams to recommend mitigations, support secure development practices, and contribute to training content that reflects real-world security scenarios.
Qualifications
Strong cybersecurity foundation, including threat modeling, vulnerability assessment, and secure architecture principles.
Hands-on experience with application security, including secure coding practices, web and API testing, and common vulnerabilities (e.g., OWASP Top 10).
Proficiency in red teaming activities, such as simulated adversarial attacks, social engineering scenarios, and post-exploitation techniques.
Ability in reverse engineering, including working with binaries, debuggers, and disassemblers to understand and analyze software behavior.
Experience with malware analysis, including dynamic and static analysis, sandboxing techniques, and behavior-based detection.
Familiarity with common penetration testing tools (e.g., Burp Suite, Nmap, Metasploit, Wireshark) and scripting languages such as Python or Bash.
Relevant certifications (e.g., OSCP, OSCE, CEH, GPEN) or equivalent practical experience in offensive security.
Strong written and verbal communication skills, including the ability to produce clear technical reports and explain findings to non-technical stakeholders.
Ability to work independently in a remote environment, manage multiple assessments, and collaborate effectively across distributed teams.
Interest in education, mentoring, or curriculum support for learners entering cybersecurity and offensive security fields.

Work arrangement
Yes