Executive Assistant to the CEO

DRW•Chicago, IL

3d•Onsite

About The Position

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.

Requirements

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.
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.
Energized by a dynamic environment where priorities and schedules evolve constantly, and sees continuous re-planning as part of the job, not a disruption.
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.

Nice To Haves

Familiarity with financial markets and trading environments is a plus.

Responsibilities

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.
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.
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 hands-on personal assistance as needed, including personal shopping, day-to-day requests and gifting, with professionalism, discretion and sound judgment.
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.
Partner closely with the CEO's private office and personal staff to coordinate schedules, share information and keep his professional and personal priorities aligned.