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Head of Trading Operations, Algorithmic Trading Group

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: DRW Montreal
Full Time position
Listed on 2026-05-16
Job specializations:
  • IT/Tech
    Crypto & DeFi
Salary/Wage Range or Industry Benchmark: 150000 - 200000 USD Yearly USD 150000.00 200000.00 YEAR
Job Description & How to Apply Below

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.

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 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…
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