Cybersecurity Penetration Testers (Chicago Airport)

Job Title: Penetration Testers
4 Openings (Junior- SME Level)
Location: Chicago, Illinois
Type: Contract
Contractor Work Model: Onsite (Chicago O' Hare and Midway Airports or nearby)
Hours: OVERNIGHT 8pm - 4am
Security Clearance: Per Federal Contract U.S citizenship required, Must be able to pass DHS background check for airport badge
Must hold one or more of the following certifications: GPEN, GWAPT, GISF, GXPN, OSCP, OSCE, OSWP, OSEE, CISSP, or CEH.

Job Details
Test Managers and Network Engineers to support cybersecurity assessments and penetration testing at Chicago's O'Hare and Midway Airports.

Project Details:

• Work is part of a cybersecurity assessment initiative
• Project Start date November 1 st 2025
• Duration: roughly 35-90 days, full-time (40 hours/week).
• Work will occur simultaneously at both airports.

Work Hours:

• Typically evenings/overnight to avoid impacting operations.
• Expected schedule: 8 p.m. - 4 a.m., though it may vary between 5 p.m. and midnight.

Work Location & Requirements:

• Positions will be on-site or in adjacent airport buildings.

Job Focus:

• Phase 1: Network and IT environment penetration testing and cybersecurity assessments.
• Phase 2: May include OT (Operational Technology) systems like scanners and specialized airport equipment.

Skills & Certifications:

• Desired certifications: CISSP (preferred), but CASP+ or CISA may be accepted as equivalents.
• College degree required (experience cannot substitute).
• Core skills: penetration testing, cybersecurity assessment, and network security.

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/ SME Level: Bachelor's degree with 15 years of professional experience or Master's degree with 13 years of professional experience.

Required Qualifications:

• Bachelor's degree in related discipline
• Conduct penetration testing operations in accordance with DHS and industry best practices.
• Safely execute testing activities under defined operational guidance
• Document findings in detailed reports with actionable remediation recommendations.
• Perform web application, network, and infrastructure testing using both commercial and open-source tools.
• Minimum of 3 years of experience in at least one of the following areas: incident detection and response, malware analysis, or cyber forensics.
• Experience with at least 3 of the following tools:
  • Kali Linux
  • Metasploit
  • Burp Suite
  • Nmap
  • Cobalt Strike
  • Tenable Nessus
  • WebInspect
  • Scuba
  • AppDetective

Ref: #850-Rockville (ALTA IT)

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.