Penetration Testers

If interested please reach out to Julianna Spicer at

Job Title: Penetration Testers
Location: Chicago, Illinois
Type: Contract
Contractor Work Model: Onsite
Hours: 8pm - 4am


Job Overview
We are seeking several Penetration Testers to join our client's Chicago cybersecurity team. This role will support penetration testing operations across applications, networks, and enterprise environments. The ideal candidate will bring deep technical expertise, proven experience in vulnerability research and exploitation, and the ability to work collaboratively within an offensive security team.

There are three levels of experience required for this position:

1. Entry Level: Bachelor's degree with 3 years of professional experience or Master's degree with 1 year of professional experience.
2. Mid Level: Bachelor's degree with 8 years of professional experience or Master's degree with 6 years of professional experience.
3. Senior Level: Bachelor's degree with 15 years of professional experience or Master's degree with 13 years of professional experience.

Primary Responsibilities

• Conduct penetration testing operations in accordance with DHS and industry best practices.
• Perform web application, network, and infrastructure testing using commercial and open-source tools.
• Safely execute testing activities under defined operational guidance.
• Document findings in detailed reports with actionable remediation recommendations.
• Collaborate with SOC, engineering, and defensive security teams to validate and remediate vulnerabilities.
• Contribute to tool development, methodology refinement, and knowledge-sharing across the team.

Required Qualifications

• Bachelor's or Master's degree in a related discipline (see experience levels above).
• Minimum of 1 year of experience in at least one of the following areas:
• Incident detection and response
• Malware analysis
• Cyber forensics

Experience with at least 3 of the following tools:

• Kali Linux
• Metasploit
• Burp Suite
• Nmap
• Cobalt Strike
• Tenable Nessus
• WebInspect
• Scuba
• AppDetective

• Must hold one or more certifications: GPEN, GWAPT, GISF, GXPN, OSCP, OSCE, OSWP, OSEE, CISSP, or CEH.

Preferred Qualifications

• Prior IT security or audit experience
• Previous system administration experience
• IT experience in a Computer Science discipline

System One, and its subsidiaries including Joul, ALTA IT Services, TeamPeople, and Mountain Ltd., are leaders in delivering outsourced services and workforce solutions across North America. We help clients get work done more efficiently and economically, without compromising quality. System One not only serves as a valued partner for our clients, but we offer eligible employees health and welfare benefits coverage options including medical, dental, vision, spending accounts, life insurance, voluntary plans, as well as participation in a 401(k) plan.

System One is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, age, national origin, disability, family care or medical leave status, genetic information, veteran status, marital status, or any other characteristic protected by applicable federal, state, or local law.