Executive Assistant to the CEO

About the role

The CEO of a respected Chicago real estate investment firm needs a sharp, discreet Executive Assistant to keep a complex calendar — and a busy executive office — running flawlessly. This is a high-trust seat with genuine exposure to deal-making, investors, and firm leadership. The right person quickly becomes indispensable.

What you'll do

• Own and defend a dynamic executive calendar across multiple time zones, resolving conflicts before they become problems
• Coordinate complex domestic and international travel — flights, hotels, ground transport, and detailed itineraries
• Plan and stage board meetings and investor communications, from logistics to materials
• Prepare briefing documents, agendas, presentations, and crisp meeting follow-ups
• Act as the polished first point of contact for the executive office, by phone, email, and in person
• Process expense reports and manage key vendor and office relationships
• Run special projects and time-sensitive administrative tasks as they arise
• Handle highly confidential information with absolute discretion

The environment

A polished Loop office steps from the Brown Line. Five days on site with occasional flexibility, a collaborative leadership team, and a firm that genuinely values this role rather than treating it as overhead.

Compensation & benefits

• $70,000–$85,000 base plus a discretionary annual bonus
• Full medical, dental, and vision coverage and a 401(k) with match
• Pre-tax commuter benefits and a well-run, well-stocked office
• Direct mentorship from a seasoned executive