offensive security engineer 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...

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, 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...

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...

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...

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...

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...

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 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...

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...

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...

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,...

McMaster-Carr is a leading e-commerce company that industrial customers have trusted for 125 years. Our products help them get manufacturing lines back up quickly, keep operations running smoothly, and prototype the next generation of innovative solutions. We earn and keep that trust by offering the right products, making them easy to find, and delivering...

TalentFish seeks a Security Engineer II to strengthen cybersecurity posture through security controls, incident response leadership, and risk/compliance support. Hybrid role with onsite Chicago-area locations a couple of days per month. The ideal candidate brings 4+ years in cybersecurity engineering, hands-on scripting (Python/PowerShell), and knowledge of...

Outlier helps the world’s most innovative companies improve their AI agents by providing human feedback. Do you want to shape the future of autonomous agents like OpenClaw? We collaborate with leading AI organizations to train LLMs to function as proactive, multi-step agents, focusing on designing, coordinating, and optimizing real-world workflows. Whether...