Senior Offensive Security Engineer

As a Senior Offensive Security Engineer at DRW, you'll lead the development of our offensive security capability. 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 to help us find and fix weaknesses before attackers do. You'll work closely with our security, infrastructure, and trading teams to translate findings into real improvements and help shape the methodology, tooling, and roadmap for offensive security at DRW.

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 you bring

• 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 such as Cobalt Strike, Metasploit, BloodHound, Burp Suite, and 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, with the ability to translate technical findings into risk that both engineers and executives understand
• A collaborative mindset: you see red teaming as a way to make the whole organization more secure, not just to find flaws

Nice to have

• 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

About DRW

DRW is a diversified trading firm with over three decades of experience, 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, and have expanded into real estate, venture capital, and cryptoassets.