Head of Trading Operations, Algorithmic Trading Group (Chicago)

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

• Work with experienced traders (average tenure of 10+ years) in a large, collaborative team.
• Interact closely with research, software, and hardware experts who support all aspects of running a sophisticated trading operation.
• Gain exposure to multiple complex strategies across markets within a team that has a proven two-decade track record of success.

Key Responsibilities

• Manage traders and trading schedules to ensure redundancy, reliability, and business continuity of trading operations (including on-call coverage and disaster recovery).
• Lead and own all aspects of trading operations with an ongoing emphasis on maximizing trading desk performance, automation and process improvement.
• Develop and refine operational protocols with researchers, developers, and traders to optimize the operation and communication of the trading desk.
• Manage and drive the UX/UI team to improve trading UIs and processes that improve efficiency, reduce errors, and enhance trader workflows.
• Maintain and improve systems and processes related to position management, back office, clearing, and exchange relationships; ensure accuracy, timeliness, and regulatory/compliance alignment.
• Define and track KPIs for desk operations (uptime, incident response times, error rates, etc.) and drive continuous improvement.
• Lead data-driven decision making; partner with researchers and developers to develop dashboards, automations, and alerting.
• Enhance communication and training among traders to standardize processes, ensure reliable operation of trading systems, and foster a culture of ownership and excellence.

Qualifications And Experience

• 10+ years of experience in financial markets, desk operations, or equivalent leadership roles within a trading environment; experience overseeing trading systems and operations.
• Demonstrated track record in automation, process optimization, and driving measurable improvements in trading operations.
• Strong understanding of position management, trade capture, settlement, clearing, and exchange processes; familiarity with multiple asset classes preferred.
• Experience leading cross-functional teams (traders, researchers, software developers, UX/UI designers, risk/compliance).
• Proven ability to design and implement effective processes, controls, incident management, and disaster recovery plans.
• Excellent leadership, communication, and stakeholder-management skills; able to influence at all levels and foster collaboration.
• Technical aptitude: comfort with data tooling and scripting 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

• Improved desk uptime and reliability with reduced incident response times.
• Higher efficiency and reduced human error through automation and streamlined workflows.
• Clear procedures for all core desk operations.
• Strong, collaborative relationships across researchers, developers, traders, and risk/compliance teams.
• A scalable, resilient operating model with robust redundancy.

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.

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