Consultant, Penetration Tester in Chicago, Illinois at Coalfire Systems

Join a collaborative and dynamic team of cybersecurity professionals to conduct cutting-edge penetration testing across a wide range of technologies and environments. As a Consultant, you’ll play a key role in identifying vulnerabilities, simulating real-world cyberattacks, and helping our clients strengthen their security posture.

Your day-to-day will include internal and external network penetration testing, application security assessments (browser-based, API, mobile), cloud environment testing, social engineering engagements, and wireless assessments.

· Perform security assessments across various platforms and technologies

· Simulate sophisticated cyberattacks to assess and improve client defenses

· Advise clients on technical security and compliance best practices

· Manage your own testing priorities and deliver high-quality work on time

· Collaborate with internal teams—PMs, QA, sales, and other consultants—to deliver exceptional client service

· Create and maintain testing methodologies, documentation, and processes

· Write detailed, high-quality reports for both technical and executive stakeholders

· Scope and lead penetration testing engagements from start to finish

· Help resolve escalations during active assessments

· Mentor junior team members and contribute to a positive team environment

· Support the team’s success by contributing to KPIs, innovation, and knowledge sharing

· A Bachelor’s Degree (or equivalent experience) in Information Security, Computer Science, or a related field

· 3+ years of hands-on experience in network and/or application penetration testing

· Proficiency with scripting languages such as Python, PowerShell, Shell, or Ruby

· Familiarity with security frameworks (e.g., PCI, HIPAA, FEDRAMP, HITRUST, or FISMA)

· 1–3 years of experience in IT security audit and/or compliance roles

· Strong technical foundation in networks, servers, workstations, and applications

· Experience working in a consulting or client-facing role (minimum 3 years)

· Strong communication and presentation skills—able to interface with both technical and non-technical stakeholders

· Willingness to travel occasionally (up to 10%)

You should have solid proficiency in at least one of the following areas:

· Compliance-Driven Penetration Testing (e.g., PCI, FedRAMP)

· Cloud Penetration Testing (e.g., AWS, Azure, GCP)

· Network/Active Directory Penetration Testing

· Application (Web/API/Mobile/Thick) Penetration Testing

· Secure Code Review

· Hardware or IoT Testing

· Container Security Testing

· AI or ML System Testing

· Proven ability to manage time and juggle multiple tasks under tight deadlines

· Strong consulting presence—can lead client meetings, kickoff calls, and present findings clearly

· Excellent report writing skills—capable of drafting both technical detail and executive summaries

· Continuous learning mindset—actively pursuing certifications and keeping up with threat landscapes