Senior Penetration Testing Engineer
About The Position
In this hybrid role based at our Chicago Headquarters, you will plan, execute, and report on penetration tests with a focus on web applications and web APIs across both internally developed and vendor SaaS solutions. Perform hands‑on offensive security testing to identify, validate, and drive remediation of vulnerabilities in modern application and API architectures. Support targeted testing of related infrastructure, cloud services, and internal systems as needed. Work with software engineering, application security, and cyber threat mitigation teams to strengthen the organization’s overall security posture.
Requirements
- Minimum - 4 Year Bachelors Degree in Computer Science, Cybersecurity, Information Systems or related
- Minimum - 3 Years of Penetration testing, offensive security or related
- 6 Years of Penetration testing, offensive security or related (In Lieu of Education)
Nice To Haves
- Industry certifications such as OSWE, OSCP, OSCE, GPEN, GWAPT, CRTO, or related offensive security credentials
Responsibilities
- Perform hands-on penetration testing with a primary focus on web applications and web APIs across homegrown and vendor systems, support testing of cloud, mobile, and internal systems.
- Conduct manual and automated testing, including authenticated and unauthenticated attack scenarios.
- Identify, exploit, and validate vulnerabilities, provide realistic assessments of risk and impact.
- Develop proof‑of‑concept exploits and document attack paths when appropriate.
- Work with development teams to guide remediation efforts, provide recommendations, review fixes, validate resolutions, and retesting.
- Collaborate proactively with engineering through threat assessments, threat modeling, and “what‑could‑go‑wrong” reviews before code is written.
- Analyze and prioritize vulnerability findings based on exploitability, severity, and business impact.
- Produce clear, actionable penetration test reports tailored for technical and non‑technical audiences.
- Present findings and trends to engineering teams, security leadership, and management.
- Contribute to improving internal testing methodologies, tooling, and standards.
- Stay current on emerging threats, attack techniques, and best practices relevant to modern web applications, APIs, and cloud environments.
Benefits
- health care
- vision
- dental
- 401k with employer match
- Annual performance bonus
- Work from home up to 3 days a week
- Paid parental leave
- Employee discount programs
- Time off including paid personal and sick days
- 11 paid holidays
- Education reimbursement
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What This Job Offers
Job Type
Full-time
Career Level
Senior
