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 or a person who was discharged or released from active duty because of a service‑connected disability. A "recently separated veteran" means any veteran during the three‑year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service. An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense. An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.