Executive Assistant to CEO and Associate Chief of Staff

Position: Executive Assistant to the CEO and Associate Chief of Staff

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Executive Assistant to the CEO and Associate Chief of Staff

HR & Risk Oak Brook, IL, US

Salary Range: $90,000.00 To $ Annually

The Executive Assistant to the CEO and Associate Chief of Staff is a strategic partner to the CEO and Executive Leadership Team and the operational hub of the corporate office. Operating with a high degree of autonomy, this role anticipates needs before they surface, connects work across departments, and turns leadership priorities into executed outcomes, from Board of Directors meetings and strategy sessions to company-wide communications, employee engagement, and process improvement.

The role leads administrative staff, owns key corporate budgets and vendor relationships, and serves as a trusted liaison to the Board, the Executive Leadership Team, and external partners. The ideal candidate is a proactive, resourceful problem-solver who exercises sound judgment, handles highly confidential information with discretion, and keeps the business moving across competing priorities.

Strategic Partnership & Executive Support

• Serve as a strategic partner to the CEO and Executive Leadership Team, anticipating needs, identifying gaps, and driving priorities and follow-through across the leadership team.
• Act as the central connection point between the Executive Leadership Team, departments, and internal/external stakeholders, ensuring information, decisions, and action items move across the organization.
• Lead the preparation of executive-level presentations, reports, and briefing materials, synthesizing input from multiple teams into polished, decision-ready deliverables.
• Draft and edit executive communications on behalf of the CEO and Executive Leadership Team.
• Manage Executive Leadership Team calendars, meeting preparation, correspondence, and follow-up actions, ensuring alignment of priorities and efficient use of leadership time.
• Coordinate, schedule, and facilitate internal and external meetings, leadership off‑sites, strategy sessions, and client engagements, including agendas, pre-work, and materials.
• Coordinate domestic and international travel, including flights, accommodations, and itineraries.
• Handle highly confidential and sensitive information, including executive, board, personnel, and financial matters, with discretion and sound judgment.
• Coordinate executive signature routing and help maintain corporate records as needed.
• When assigned, serve as the point person when an executive is unexpectedly unavailable, managing their calendar, inbox, and internal and external communications.

Board of Directors Support

• Serve as the primary point of contact for Board of Directors meeting logistics and communications, partnering closely with the CEO.
• Coordinate the development of quarterly Board materials, collecting content from executive and department leaders and building the board deck and agenda.
• Record and prepare Board meeting minutes and track resulting action items.
• Plan and execute Board meetings, strategy sessions, site visits, and related events, including venue and hotel contracts, room blocks, dinners, and attendee communications.

Strategic Projects & Operational Leadership

• Lead cross-functional projects on behalf of the CEO and Executive Leadership Team from concept through completion, such as facility searches, new program rollouts, and corporate contract renewals.
• Establish and run the operating rhythm for cross-functional working groups, including meeting cadence, prep and debrief templates, and facilitation.
• Proactively identify operational gaps and inefficiencies, then design and implement the systems, tools, and processes to solve them.
• Analyze vendor quotes, contracts, and terms, and make recommendations that balance cost, risk, and business needs.
• Partner with outside consultants, brokers, and advisors to advance company initiatives.
• Partner with outside brand advisors and Marketing on company rebrand and culture initiatives.
• Integrate acquired companies, including the UK business, into Executive Leadership Team, Board, and company programs.
• Support a workforce across four companies on separate Microsoft environments, building workarounds for cross-company communications and processes.
• Partner with Marketing on corporate sponsor ships, charitable giving, and industry memberships.
• Step in to provide interim coverage when critical roles or functions are…