Offensive Security Engineer - CISSP/OSCP - Chicago, IL

Job Description A well-established organization is seeking an Offensive Security Engineer to join its cybersecurity team in Chicago, IL. This role is ideal for a hands-on security professional who thrives on identifying vulnerabilities before adversaries can exploit them. You will be responsible for conducting penetration testing, vulnerability assessments, adversary simulation activities, and security validation across enterprise environments.
This position offers the opportunity to work closely with infrastructure, cloud, application development, and security teams to strengthen the organization's security posture. The ideal candidate combines strong technical expertise with the ability to clearly communicate findings and remediation recommendations to both technical and business stakeholders.
This is a hybrid position requiring three days per week in the Chicago office. Required Skills & Experience

• CISSP (Certified Information Systems Security Professional) certification
• OSCP (Offensive Security Certified Professional) certification
• 4+ years of experience in offensive security, penetration testing, or security engineering
• Strong experience conducting network, web application, cloud, and infrastructure penetration testing
• Experience performing vulnerability assessments and risk analysis
• Knowledge of common attack frameworks, including MITRE ATT&CK and OWASP Top 10
• Proficiency with penetration testing and security assessment tools such as Burp Suite, Nmap, Metasploit, Nessus, BloodHound, Cobalt Strike, or similar
• Experience identifying, exploiting, and documenting security vulnerabilities
• Understanding of Windows, Linux, Active Directory, networking, and cloud platforms
• Scripting or automation experience using Python, PowerShell, Bash, or similar languages
• Strong report-writing and communication skills

Desired Skills & Experience

• Experience conducting red team engagements or adversary emulation exercises
• Knowledge of cloud security assessments within AWS, Azure, or Google Cloud environments
• Security certifications in addition to CISSP and OSCP, such as GPEN, CRTO, GWAPT, or CEH
• Experience evaluating CI/CD pipelines and application security controls
• Familiarity with threat intelligence and threat hunting methodologies
• Experience supporting compliance frameworks such as NIST, ISO 27001, PCI-DSS, or SOC 2

What You Will Be Doing Daily Responsibilities

• Conduct internal and external penetration testing across enterprise environments
• Perform vulnerability assessments and validate remediation efforts
• Execute web application, network, cloud, and wireless security testing
• Simulate real-world attack scenarios to identify security weaknesses
• Partner with engineering and infrastructure teams to prioritize remediation activities
• Develop detailed reports outlining findings, business impact, and recommended corrective actions
• Participate in red team exercises and security validation initiatives
• Assist in improving offensive security methodologies, tooling, and testing standards
• Stay current on emerging threats, attacker techniques, and industry best practices

Daily Breakdown

• 80% Hands-On Offensive Security Testing
• 20% Reporting, Collaboration, and Security Consulting

The Offer

• Competitive salary up to $145,000
• Hybrid work schedule (3 days onsite in Chicago, 2 days remote)
• Opportunity to work on complex enterprise security initiatives
• Exposure to modern cloud and infrastructure security technologies
• Career growth within a collaborative cybersecurity team

You will receive the following benefits

• Medical Insurance
• Dental Benefits
• Vision Benefits
• Paid Time Off (PTO)
• 401(k)

Applicants must be currently authorized to work in the US on a full-time basis now and in the future.