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Executive Assistant, CEO

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.

The Executive Assistant (EA) to the CEO provides strategic, high-touch support in a fast-paced, market-driven environment. This role serves as an extension of the CEO—owning complex scheduling and prioritization, managing sensitive communications, driving follow-through on critical initiatives, and coordinating across senior stakeholders internally and externally. The ideal candidate is highly proactive, exceptionally organized, discreet, and comfortable operating with autonomy amid rapidly changing priorities and time-sensitive matters.

What you will be working on:

Strategic Executive Support & Time Optimization

  • Act as a trusted partner to the CEO, anticipating needs and proactively removing friction from day-to-day operations.
  • Anticipate issues and initiate appropriate action to ensure the most effective use of the CEO’s time, including creating structure, prioritization frameworks, and clear daily/weekly rhythms.
  • Prepare the CEO for meetings by ensuring materials are complete, accurate, and delivered in advance; highlight key decisions, deadlines, and risks.

Complex Calendar, Travel & Meeting Management

  • Coordinate internal and external meetings across multiple time zones; prepare and circulate agendas and materials; ensure timely follow-ups.
  • Coordinate logistics as needed (e.g., travel, virtual meeting setup, onsite arrangements), ensuring smooth execution.
  • Maintain personal and professional calendar and communicate adjustments/changes on a regular basis.

Cross-Functional Leadership & External Partner Coordination

  • Coordinate with senior leaders and key teams (executives, trading, risk, compliance, legal, HR) to align schedules, track deliverables, and support business-critical workflows.
  • Maintain strong working relationships with internal stakeholders and external partners; represent the CEO’s office with credibility and tact.

Executive Materials & Operational Administration

  • Review incoming email and use judgement to assess urgency, remove irrelevant messages, provide standard reply, and escalate as required.
  • Draft partner communications and assist in preparing presentations.
  • Address other day-to-day administrative needs: filing, invoices, expense preparation, bills, tax documents, etc.
  • Provide personal support as needed while maintaining professionalism, discretion, and appropriate boundaries.

Skills and Competencies

  • Education: Bachelor’s degree in Business Administration, Finance, Economics, or a related field; or equivalent professional experience.
  • 7+ years of progressive experience supporting C-suite executives, including significant experience supporting a CEO or equivalent senior leader.
  • Industry Knowledge: Familiarity with financial markets, trading workflows, risk/compliance concepts, and market hours.
  • Executive-level communication skills (written and verbal) with strong judgment, polish, and the ability to interface credibly with senior leadership and external partners.
  • Exceptional organizational and time-management capabilities; proven ability to handle high volume, competing priorities, and last-minute changes.
  • Highly proactive and autonomous—able to identify needs, propose solutions, and drive outcomes without extensive direction.
  • Demonstrated discretion and integrity; trusted with confidential information and sensitive relationships.
  • Problem-solving mindset, proactive approach, and the ability to anticipate needs before they arise.
  • Adaptable and resilient; able to support extended hours during market events, urgent matters, or key deadlines.

Work Environment

  • Fast-paced, high-intensity trading environment; high standards for accuracy and speed.
  • On-site presence preferred/required at the office; sensitive to market hours and international time zones.
  • May involve evening or weekend work around major market events or key deadlines.

The annual base salary range for this position is $100,000 to $200,000 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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