Senior Offensive Security Engineer

About DRW At DRW, we identify and capture trading and investment opportunities globally. What sets us apart is our diversified approach—trading across many asset classes and instruments, in markets around the world, with horizons from seconds to years. We succeed by leveraging technology, research and risk management. We offer the best of both worlds: the opportunity and spirit of a startup and the benefits and stability of an established, experienced firm. Our employees work hard to solve interesting problems, and their results are rewarded. We value continuous learning—from our outcomes, from the environment and from each other. It’s a place of high expectations, deep curiosity, and constant collaboration, with some of the smartest, most passionate people you’ll meet. // Chez DRW, nous identifions et saisissons les opportunités de négociation et d'investissement au niveau mondial. Ce qui nous différencie, c'est notre approche diversifiée : nous négocions sur de nombreuses classes d'actifs et d'instruments, sur des marchés du monde entier, avec des horizons allant de quelques secondes à plusieurs années. Nous réussissons en nous appuyant sur la technologie, la recherche et la gestion des risques. Nous offrons le meilleur des deux mondes: les opportunités et l'ésprit d’une entreprise en démarrage, et les avantages et la stabilité d'une entreprise établie et expérimentée. Nos employés travaillent dur pour résoudre des problèmes intéressants et leurs résultats sont récompensés. Nous valorisons l'apprentissage continu – de nos résultats, de l’environnement et de chacun de nous. C’est un lieu où les attentes sont élevées, la curiosité est profonde et la collaboration est constante, et où l’on retrouve quelques-uns des individus les plus intelligents et les plus passionnés que vous puissiez rencontrer.

DRW

tradingtechnologyresearchnégociationtechnologieand recherche

D

drw.com/careers

1,001-5,000 employees

Financial Services

Chicago, IL

Privately Held

105k LinkedIn followers

• 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

• 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.

• Group medical insurance
• Pharmacy insurance
• Dental insurance
• Vision insurance
• 401k
• Short-term disability
• Long-term disability
• Life insurance
• AD&D insurance
• Health savings accounts
• Flexible spending accounts
• Discretionary bonus