offensive security jobs in Chicago

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk.Headquartered in Chicago with offices...

Senior Offensive Security Engineer Chicago preferred | NYC / London | Remote considered Compensation open - scope to exceed your current package I'm working on a talent-led search for a Senior Offensive Security Engineer to join a highly technical global financial organisation building out its offensive security capability. This isn't a role where you'll...

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk. Headquartered in Chicago with offices...

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk. Headquartered in Chicago with offices...

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk.Headquartered in Chicago with offices...

DRW, a diversified trading firm based in Chicago, seeks a Senior Offensive Security Engineer to lead red team engagements, adversary simulations, and vulnerability testing across trading systems, corporate IT, and cloud platforms. You’ll develop tooling, coordinate with Security Engineering and SOC, and drive improvements to make DRW harder to...

Offensive Security Analyst (Structured / Non-Exploit) — AI Training About The Role What if your ability to trace an attacker's footsteps — mapping kill chains, spotting defensive gaps, and modeling adversary behavior — could directly shape how the world's most advanced AI systems understand cybersecurity? We're looking for Offensive Security...

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,...

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, pen tests, and adversary simulations across trading systems, IT, and cloud platforms. You will translate findings into real improvements and help shape tooling and roadmap for offensive security at DRW.You will work with security, infrastructure, and trading teams to ensure...

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, plan adversary simulations, and test trading systems, IT, and cloud platforms. You will translate findings into actionable improvements and help mature DRW's offensive security program.You will design custom tooling, collaborate with SOC, run phishing simulations, and track...

DRW, a Chicago-based trading firm, is expanding its offensive security program and seeks a Senior Offensive Security Engineer to lead red-team engagements, tests, and adversary simulations across trading systems and cloud platforms.You will design methods, build tooling, and guide improvements with security teams, helping to make the firm harder to...

R1 RCM Inc. is seeking a Senior IT Security Engineer to strengthen vulnerability discovery and remediation across infrastructure, networks, and applications. This role spans multiple cloud environments (AWS, Azure, and GCP) and involves building tooling and maturing testing processes in a healthcare tech setting. As an individual contributor, you will run...

Grant Thornton is seeking a Senior Offensive Security Consultant to lead adversarial testing engagements across industries. You will simulate real-world attackers, validate detections, and help clients strengthen their security posture through actionable reporting and executive communications.The role demands hands-on penetration testing across networks,...

Senior Offensive Security Engineer Chicago preferred | NYC / London | Remote considered Compensation open - scope to exceed your current package I’m working on a talent-led search for a Senior Offensive Security Engineer to join a highly technical global financial organisation building out its offensive security capability. This isn’t a role where...

Job-ID: 116021Category: -Location: Philadelphia, PA, United States; New York, NY, United States; Boston, MA, United States; Arlington, VA, United States; Charlotte, NC, United States; Chicago, IL, United States; Atlanta, GA, United States; Houston, TX, United States; Dallas, TX, United States; Austin, TX, United StatesSchedule: Full timePosted: 2026-10-22As...

R1 RCM Inc. is seeking a Senior IT Security Engineer to strengthen vulnerability discovery and remediation across infrastructure, networks, and applications.This role spans multiple cloud environments (AWS, Azure, and GCP) and involves building tooling and maturing testing processes in a healthcare tech setting. As an individual contributor, you will run...

Your Journey at Crowe Starts Here:At Crowe, you can build a meaningful and rewarding career. With real flexibility to balance work with life moments, you’re trusted to deliver results and make an impact. We embrace you for who you are, care for your well-being, and nurture your career. Everyone has equitable access to opportunities for career growth and...

PhD Intern — Offensive Security & AICompany: Hawksbill Location: Honolulu, Hawaii / remote eligibility About the RoleHawksbill develops offensive security capabilities that help organizations discover exploitable weaknesses, understand their consequences, and verify that defenses work. We combine hands-on security research with AI to advance...

McMaster-Carr, a leading industrial supply e-commerce company, seeks a Senior Offensive Security Engineer to build and operate an independent security assurance program within Internal Audit. You will run risk-based penetration tests, adversary simulations, and purple-team engagements across enterprise systems, networks, and cloud environments.You will...

DRW, a Chicago-based trading firm, is expanding its offensive security program and seeks a Senior Offensive Security Engineer to lead red-team engagements, tests, and adversary simulations across trading systems and cloud platforms. You will design methods, build tooling, and guide improvements with security teams, helping to make the firm harder to...