Executive Assistant to the CEO

DRW; Chicago (IL); On-site; USD 100,000 - 200,000; Full time

Benefits offered by this job

Group medical, pharmacy, dental and V

401k with discretionary employer match

Short and long-term disability

Life and AD&D insurance

Health savings accounts

Flexible spending accounts

Job summary

DRW in Chicago seeks a strategic Executive Assistant to the CEO. This high-touch role partners with the CEO to optimize time, refine routines, and manage priority communications across business and personal affairs.

Responsibilities include complex scheduling across time zones, travel planning, and preparing meeting materials. The position requires operational discretion, integrity, and extensive experience supporting C-suite leaders.

Qualifications

• Bachelor's degree or equivalent professional experience.
• 7+ years supporting C-suite executives or principals, including CEO-level support.
• Familiarity with financial markets and trading environments is a plus.
• Strategic systems thinker who refines processes and adapts to preferences.
• Exceptional organizational and time-management abilities with high-volume priorities.
• Executive-level written and verbal communication with credibility and discretion.
• Unquestionable discretion and integrity; trusted with confidential information.

Responsibilities

• Act as a trusted partner to the CEO, anticipating needs and removing friction.
• Manage complex scheduling and travel across multiple time zones; prepare materials for meetings.
• Draft correspondence and briefing materials; manage CEO's inbox with prioritization.
• Coordinate with senior leaders and external partners; track deliverables and risks.
• Maintain organized records of relationships and contacts for CEO engagement.

Skills

Strategic systems thinker

Discretion and integrity

Executive communication

Time-management

Cross-functional collaboration

Client/partner relations

Adaptability under pressure

Service-oriented mindset

Education

Bachelor's degree or equivalent

Job description

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 is a strategic, high-touch role supporting the CEO across his business and personal affairs. Working in close partnership with the CEO, the EA helps him make the most of his time by understanding how he operates, anticipating needs and continuously refining the processes that support his work. Key responsibilities include managing complex scheduling and travel, prioritizing communications, coordinating with senior leaders and external partners, and tracking open items. The ideal candidate is a strategic systems thinker who is exceptionally organized, discreet and service-oriented. They adapt to the CEO's working style and thrive amid rapidly changing priorities in a fast-paced environment.

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. Develop a deep understanding of how the CEO works, including his preferences, priorities and rhythms. Use it to continuously refine the processes and routines that support him, proposing improvements and adapting to his working style. Help protect the CEO's time by anticipating conflicts and competing demands, and bringing forward the information he needs to decide where his time goes. Prepare the CEO for meetings by ensuring materials are complete, accurate, and delivered in advance; highlight key decisions, deadlines, and risks. Maintain clear documentation of the CEO's preferences, key processes and contacts, so that his support stays consistent and resilient.

Complex Calendar, Travel & Meeting Management

Manage the CEO's professional and personal calendar, balancing competing demands across multiple time zones. Anticipate conflicts and surface trade-offs for his decision. Plan end-to-end travel from the CEO's objectives: itineraries, relevant meetings and logistics, with all arrangements coordinated for smooth execution. Coordinate internal and external meetings, including scheduling, agendas, materials, and virtual or onsite arrangements. Maintain a forward-looking view of the CEO's schedule and keep the relevant teams and stakeholders informed of plans and changes, so they can prepare in advance.

Communications & Operational Administration

Manage the CEO's inbox by filtering, categorizing and prioritizing incoming communications, surfacing what needs his attention, and responding within agreed guidelines. Draft correspondence and partner communications for the CEO's review, and assist in preparing presentations and briefing materials. Manage expenses, receipts, invoices and related documentation across business and personal accounts, coordinating with finance and accounting teams as needed. Handle day-to-day administration, including filing, records and documentation, with accuracy and confidentiality. Provide personal support across the CEO's broader affairs with professionalism, discretion and sound judgment.

Cross-Functional Leadership & External Partner Coordination

Coordinate with senior leaders and teams across the CEO's business and personal operations to align schedules, track deliverables, and keep the CEO informed on key workflows. Serve as a trusted point of contact for the CEO's internal and external network, representing his office with credibility, discretion and tact. Maintain an organized record of the CEO's key relationships and contacts, including context, history and priorities, to support how he engages his network.

Skills and Competencies

• Bachelor's degree or equivalent professional experience.
• 7+ years supporting C-suite executives or principals, including significant experience supporting a CEO, founder or high-profile individual directly.
• Familiarity with financial markets and trading environments is a plus.
• A strategic systems thinker who continuously refines processes, and knows when to propose changes and when to adapt to the principal's preferences.
• Exceptional organizational and time-management skills, with the ability to handle high volume, competing priorities and last-minute changes.
• Executive-level written and verbal communication, with the polish and judgment to interact credibly with senior leaders and external partners.
• Unquestionable discretion and integrity, trusted with confidential information and sensitive relationships.
• Service-oriented and low-ego, comfortable operating in the background and measuring success by the principal's effectiveness.
• Adaptable and resilient, able to support extended hours during key events, travel or urgent matters.

Work Environment

Fast-paced, high-standards environment supporting a CEO across business and personal priorities, where accuracy, speed and discretion are essential. On-site role based in the Chicago office, with awareness of market hours and international time zones. Flexibility for evening or weekend availability around travel, key events or time-sensitive matters.

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.

• 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
• flexible spending accounts

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