Senior Executive Assistant: Gatekeeper & Strategy Ally

Confidential; Chicago (IL); On-site; USD 90,000 - 120,000; Full time

Job summary

Confidential in Chicago seeks a senior Executive Assistant to serve as the right hand to a high-level executive. You will guard the executive’s time, prepare meetings, and manage confidential information with discretion.

You will own a complex calendar, triage communications, draft executive communications, and coordinate with leadership and external partners on strategic initiatives. This role requires 5–8+ years of executive support and exemplary judgment.

Qualifications

• > 5–8+ years as an Executive Assistant, including direct support to a President, C-suite exec, or business owner.
• > Track record of independent judgment and acting as trusted proxy for a senior leader.
• > Exceptional organization and ability to manage competing high-stakes priorities without dropping detail.
• > Strong written and verbal communication; able to draft in an executive's voice.
• > Demonstrated discretion with confidential personnel, compensation, or strategic information.

Responsibilities

• Serve as the primary contact and gatekeeper for a senior executive—managing access, prioritizing demands, protecting their time.
• Own and orchestrate a complex and shifting calendar.
• Triage incoming communications and requests, handling many independently and surfacing only what needs the executive.
• Prepare the executive for meetings—agendas, briefing materials, minutes, and follow-up on action items.
• Draft, edit, and send correspondence in the executive's voice with minimal direction.
• Coordinate with leadership, internal departments, and external partners on key initiatives.
• Arrange complex travel and detailed itineraries.
• Lead or support special projects, research, and presentations.
• Handle highly sensitive information with absolute discretion.
• Maintain systems, documentation, and operations that keep the executive’s office running.

Skills

Executive EA experience

Independent judgment

Organizational skills

Communication skills

Discretion with confidential info

Microsoft Office proficiency

Problem solving & follow-through

Tools

Microsoft Office

Job description

Confidential in Chicago seeks a senior Executive Assistant to serve as the right hand to a high-level executive. You will guard the executive’s time, prepare meetings, and manage confidential information with discretion.

You will own a complex calendar, triage communications, draft executive communications, and coordinate with leadership and external partners on strategic initiatives. This role requires 5–8+ years of executive support and exemplary judgment.