Executive Assistant

Connect Search, LLC; Chicago (IL); Hybrid; USD 90,000 - 130,000; Full time

Job summary

Connect Search, LLC in Chicago seeks an experienced Executive Assistant to the CEO, guiding daily priorities, coordinating board activities, and supporting communications across the organization.

The role combines executive support (calendar, travel, sensitive information), office operations, and stakeholder liaison with a mission-driven focus. 3 days/week in downtown Chicago; hybrid schedule.

Qualifications

• 10+ years supporting a CEO, President, founder, or senior executive.
• Experience managing complex calendars, travel, board meetings, and confidential communications.
• Strong Microsoft Office skills; Salesforce or other CRM experience is preferred.
• Excellent judgment, discretion, communication, and organization.
• Proactive, resourceful, detail-oriented, and comfortable balancing multiple priorities.

Responsibilities

• Executive Support (75%): manage the CEO’s calendar, priorities, travel, expenses, and follow-up items.
• Serve as the primary contact for the CEO’s office and handle sensitive information professionally.
• Prepare agendas, briefing materials, and other documents for meetings.
• Coordinate board and committee meetings, materials, minutes, and logistics.
• Maintain the CEO’s contact database and coordinate stakeholder communications.
• Organize events and maintain accurate board and organizational records.
• Coordinate with HR, Legal, and external partners as needed.
• Office and Team Support (15%): provide administrative support to other senior leaders.
• Coordinate onboarding, team events, and volunteer activities.
• Maintain organized physical and digital files.
• Support office operations, webinars, conferences, and special projects.
• Help identify practical office sustainability initiatives.
• Website and Communications (10%): Coordinate routine website updates.
• Gather and verify content for quarterly newsletters.
• Support executive communications and stakeholder materials.

Skills

Executive Support

Calendar Management

Board Coordination

Travel Arrangements

Discretion

Communication

Multi-tasking

AI Tools Familiarity

Website Platforms

Team Liaison

Tools

Salesforce

Job description

A Chicago-based, mission-driven financial institution that invests in organizations and initiatives focused on expanding access to capital, supporting underserved communities, and creating long-term economic opportunity.

The organization offers a collaborative, high-impact environment where employees work closely with senior leadership and external stakeholders.

About the role:

This position will oversee the day-to-day priorities of the CEO’s office, coordinate board and stakeholder activities, support internal operations, and assist with select communications projects. The ideal candidate is proactive, highly organized, discreet, and comfortable taking a hands-on approach within a dynamic, mission-driven organization.

3 days a week downtown Chicago - 15 min walk from Union Station

Key Responsibilities

Executive Support (75%)

• Manage the CEO’s calendar, priorities, travel, expenses, and follow-up items
• Serve as the primary contact for the CEO’s office and handle sensitive information professionally
• Prepare agendas, briefing materials, and other documents for meetings
• Coordinate board and committee meetings, materials, minutes, and logistics
• Maintain the CEO’s contact database and coordinate stakeholder communications
• Organize events and maintain accurate board and organizational records
• Coordinate with HR, Legal, and external partners as needed

Office and Team Support (15%)

• Provide administrative support to other senior leaders
• Coordinate onboarding, team events, and volunteer activities
• Maintain organized physical and digital files
• Support office operations, webinars, conferences, and special projects
• Help identify practical office sustainability initiatives

Website and Communications (10%)

• Coordinate routine website updates
• Gather and verify content for quarterly newsletters
• Support executive communications and stakeholder materials

Qualifications

• 10+ years supporting a CEO, President, founder, or senior executive
• Experience managing complex calendars, travel, board meetings, and confidential communications
• Strong Microsoft Office skills; Salesforce or other CRM experience is preferred
• Excellent judgment, discretion, communication, and organization
• Proactive, resourceful, detail-oriented, and comfortable balancing multiple priorities
• Familiarity with AI tools and website platforms is a plus
• Interest in financial services, community development, or mission-driven work is preferred