Chief of Staff

Position Overview:

Client is seeking a highly experienced Chief of Staff to provide comprehensive support to the Chief Executive Officer of a private company in Chicago, IL. This role is critical in ensuring the CEO operates efficiently and effectively by managing a broad range of executive and personal tasks. The ideal candidate will bring exceptional organizational and communication skills, a proactive mindset, and the ability to thrive in managing both business and personal needs.

Key Responsibilities include:

• 360-degree personal and administrative support to the CEO
• Manage an ever-changing and complex calendar, including scheduling internal and external meetings, conferences, and board meetings.
• Serve as the primary point of contact between the CEO and internal/external employees, business partners, and contacts.
• Draft, review, and edit communications, presentations, and reports on behalf of the CEO.
• Coordinate and prepare materials for meetings, ensuring the CEO is informed and briefed in advance.
• Plan and oversee events, including company retreats, annual celebrations, and philanthropic initiatives.
• Cultivate, liaise, and invest in the long-term best interests of company’s partners and relationships, including with employees and external investment partners.
• Attend meetings when required and track follow-ups and action items.
• Arrange complex domestic and international travel, including flights, accommodations, ground transportation, visas, and itineraries; proactively anticipate and manage changes to travel and meeting schedules.
• Serve as support with personal commitments and logistics, including appointments, reservations, family scheduling, and private events.
• Handle personal errands in coordination with household staff.
• Personal shopping, including purchasing gifts, clothing, tickets, and hard-to-procure items.
• Process and track expenses, invoices, and reimbursements.
• Maintain executive files, records, and databases.
• Ensure confidentiality and professionalism in all interactions and matters.

Qualifications:

• Bachelor’s degree required.
• 7-10+ years of experience in a c-level Executive and/or Personal Assistant role, preferably supporting a CEO or founder.
• Proven ability to maintain and manage highly confidential information.
• Excellent written and verbal communication skills.
• Strong proficiency in Microsoft Office Suite, Google Workspace, and scheduling/travel software.
• Able to work flexible hours and be available after hours as needed.
• Highly organized, with excellent time management and prioritization skills.
• Calm under pressure and able to adapt quickly to changing needs.
• Self-motivated, proactive, and capable of anticipating needs before they arise.
• Professional demeanor with a high level of emotional intelligence and discretion.
• Trustworthy, loyal, and committed to excellence.