Senior Offensive Security Engineer

DRW Holdings, LLC; Chicago (IL); On-site; USD 175,000 - 275,000; Full time

Benefits offered by this job

Group medical insurance

Dental and vision insurance

401k with discretionary match

Disability insurance

Health savings account (HSA)

Flexible spending accounts (FSA)

Job summary

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 controls are effective and drive actionable risk reductions. This is a hands-on, high-trust role focused on measurable improvement.

Qualifications

• 5+ years in offensive security, penetration testing, or red teaming across full engagement lifecycle.
• Strong scripting or programming ability for offensive tooling.
• Solid networking, OS internals, cloud platforms and identity providers knowledge.
• Experience with MITRE ATT&CK, reporting, and adversary emulation techniques.
• Familiarity with blockchain security and AI/ML security risks.

Responsibilities

• Plan and execute red team engagements and adversary simulations against trading systems, IT and cloud environments.
• Perform penetration tests across networks, web apps, APIs, and cloud infrastructure with actionable remediation guidance.
• Design and build tooling, scripts, and exploits to emulate attacker behavior and test detections.
• Collaborate with Security Engineering and SOC in purple-team exercises to close gaps.
• Run phishing simulations and assess security awareness.
• Identify and track vulnerabilities through remediation with owners.

Skills

Red teaming

Penetration testing

Scripting

Networking

MITRE ATT&CK

Reporting

Cloud security

Blockchain security

AI/ML security

Team collaboration

Tools

Cobalt Strike

Metasploit

BloodHound

Burp Suite

Nmap

Job description

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 throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets.

We operate with respect, curiosity and open minds. The people who thrive here share our belief that it’s not just what we do that matters–it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus.

About the Role

DRW is building out its offensive security capability, and we’re looking for a Senior Offensive Security Engineer to lead the charge. In this role, you’ll plan and execute red team engagements, penetration tests, and adversary simulations against our trading infrastructure, corporate environment, and cloud platforms, acting as a trusted adversary who helps us find and fix weaknesses before anyone else does.

You’ll work closely with our security, infrastructure, and trading teams to translate what you find into real improvements, and you’ll help shape the methodology, tooling, and roadmap for offensive security at DRW as the function matures. This is a hands‑on, high‑trust role for someone who thinks like an attacker, communicates like a partner, and cares about making the firm measurably harder to compromise.

What You'll Do

• Plan and execute red team engagements and adversary simulations against trading systems, corporate IT, and cloud environments, modeling realistic attacker tactics, techniques, and procedures (TTPs) mapped to frameworks such as MITRE ATT&CK
• Conduct penetration tests across networks, web and internal applications, APIs, and cloud infrastructure, and report findings with clear, actionable remediation guidance
• Design and build custom tooling, scripts, and exploits to emulate adversary behavior, test control effectiveness, and validate detection coverage
• Partner with the Security Engineering and SOC teams in purple‑team exercises to close gaps between what attackers can do and what defenders can see
• Run social engineering and phishing simulations to assess and improve organizational security awareness
• Identify, validate, prioritize, and track vulnerabilities and control weaknesses through to remediation in collaboration with infrastructure, platform, and application owners
• Present engagement results and risk narratives to both technical teams and senior leadership in a way that drives action
• Stay current on the threat landscape, emerging TTPs, and offensive tooling, and bring that knowledge back into DRW’s defenses
• Assess the security of AI and LLM‑integrated systems, including prompt injection, model manipulation, data poisoning, and abuse of agentic workflows, and work with teams building these systems to harden them
• Leverage AI‑assisted tooling to accelerate reconnaissance, vulnerability discovery, and exploit development, and evaluate new AI‑powered offensive techniques as they emerge
• Help define and mature DRW’s offensive security methodology, standards, and tooling, and mentor other engineers on the security team

What We're Looking For

• 5+ years of hands‑on experience in offensive security, penetration testing, or red teaming, including full engagement lifecycle work: reconnaissance, initial access, privilege escalation, lateral movement, persistence, and exfiltration
• Strong scripting or programming ability for building and adapting offensive tooling
• Solid understanding of networking fundamentals, Windows, macOS, and Linux internals, identity providers, and cloud platforms
• Practical experience with common offensive security tools (e.g., Cobalt Strike, Metasploit, BloodHound, Burp Suite, Nmap) and a track record of building your own when the situation calls for it
• Working knowledge of the MITRE ATT&CK framework, adversary emulation, and detection evasion techniques, along with enough understanding of defensive controls and tooling to help defenders improve
• A track record of clear, precise reporting and communication and you can translate technical findings into risk that both engineers and executives understand
• Experience with smart contract auditing and blockchain security
• Familiarity with AI/ML security risks, including adversarial attacks on models, prompt injection, and the offensive and defensive implications of LLM‑powered tooling
• A collaborative mindset: you see red teaming as a way to make the whole organization more secure, not just to find flaws

The annual base salary range for this position is $175,000 to $275,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus. In addition, DRW offers a comprehensive suite of employee benefits including group medical, pharmacy, dental and vision insurance, 401k (with discretionary employer match), short and long‑term disability, life and AD&D insurance, health savings accounts, and flexible spending accounts.

For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at https://drw.com/privacy-notice .