Senior Offensive Security Engineer

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

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