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Head of Trading Operations, Algorithmic Trading Group

DRW · Prop trading · Chicago · Posted 2026-03-15

Apply now → Applications go to DRW's own site.

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.

DRW is seeking a Head of Trading Operations for the Algorithmic Trading Group to lead the trading team, desk operations, automation, and process improvement. You will manage workflows, monitor exchange positions, and coordinate with risk and compliance. You will also partner with researchers and developers to refine operational protocols and lead UX/UI initiatives to improve reliability, reduce errors, and maximize performance of our trading strategies.

Work Environment:

Key Responsibilities:

Qualifications and Experience:

  • 10+ years experience in financial markets, desk operations, or equivalent leadership roles within a trading environment; experience overseeing trading systems and operations.
  • Experience on a trading desk managing automated trading systems and tools, strategies, orders, positions, and risk, with demonstrated ability to make sound decisions in fast-paced, high-pressure environments.
  • Strong understanding of position management, trade capture, settlement, clearing, and exchange processes; familiarity with multiple asset classes preferred.
  • Demonstrated track record in automation, process optimization, and driving measurable improvements in trading operations.
  • Proven ability to design and implement operational controls, incident-management frameworks, and disaster-recovery plans for trading environments.
  • Experience leading cross-functional teams (traders, researchers, software developers, UX/UI designers, risk/compliance).
  • Technical aptitude: comfort with data tooling, scripting and AI tools is a plus.
  • Education: Bachelor’s degree in finance, mathematics, computer science, engineering, or a related quantitative field. MBA is a plus.

What success looks like:

The annual base salary range for this position is $175,000 to $225,000 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.

California residents, please review the California Privacy Notice for information about certain legal rights at https://drw.com/california-privacy-notice.

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