Executive Assistant

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

A well-established financial services firm is conducting a confidential search for a senior level Executive Assistant to serve as the right hand to a senior executive. This is a high-trust, high-autonomy seat. You'll be the gatekeeper to the executive's time, the person who anticipates what's needed before it's asked, and the trusted holder of confidential business, personnel, and compensation information. You'll operate with significant independent judgement, represent the executive in communications across the leadership team and external partners, and keep a fast-moving office a step ahead.

What You’ll Own

• Serve as the primary point of contact and gatekeeper for a senior executive — managing access, prioritizing competing demands, and 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 and leadership sessions — agendas, briefing materials, minutes, and follow-through on action items.
• Draft, edit, and send correspondence in the executive's voice with minimal direction.
• Coordinate with the leadership team, 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 — personnel, compensation, strategic, and executive communications — with absolute discretion.
• Maintain the systems, documentation, and operations that keep the executive’s office running.

What You Bring

• 5–8+ years as an Executive Assistant, including direct support to a President, C‑suite executive, or business owner.
• A track record of operating with independent judgment and acting as a trusted proxy for a senior leader.
• Exceptional organization and the ability to manage competing high-stakes priorities without dropping detail.
• Strong written and verbal communication; able to draft confidently in an executive's voice.
• Demonstrated discretion handling confidential personnel, compensation, or strategic information.
• Advanced Microsoft Office (Outlook, Word, Excel, PowerPoint) and fluency picking up new tools.
• Sharp problem-solving, anticipation, and follow-through.

Strongly Preferred

• Experience in a regulated industry (financial services, banking, insurance, or similar).
• Familiarity with executive-level confidentiality in a compliance-driven environment.