Executive Assistant (Contract-to-Hire)

A mission-driven nonprofit organization is seeking a Contract Executive Assistant to support two C-suite leaders during an exciting phase of organizational growth and evolution. This is a highly visible 36-month contract opportunity with strong potential to convert, offering a hybrid schedule in downtown Chicago.

This role goes far beyond traditional calendar management. The team is looking for a true right hand who can help create structure, improve workflows, and build processes not only for the executives, but across the broader team as the organization continues to scale.

The ideal candidate thrives in environments where priorities shift quickly, and executive support functions are still evolving. This person will bring a proactive, solutions-oriented mindset and naturally identify opportunities to streamline communication, improve organization, and create operational efficiencies that allow leadership to stay focused on impact and strategy.

Responsibilities include:

• High-level executive support for two senior leaders
• Complex calendaring, scheduling, travel coordination, and meeting logistic
• Inbox support, communications, expense management, and follow-up coordination
• Creating and improving internal processes, systems, and workflows
• Supporting team coordination and helping establish structure across administrative operations
• Personal support responsibilities including meal coordination, scheduling support, and day-to-day logistics handled with discretion and professionalism
• Acting as a highly collaborative partner who can anticipate needs and stay several steps ahead

What theyre looking for:

• 5+ years of Executive Assistant experience supporting senior leadership
• Experience operating in fast-paced, evolving environments
• Strong process-building and organizational skills
• Comfortable with Executive Assistant / Personal Assistant overlap
• Highly proactive, adaptable, and service-oriented
• Confident communicator with strong judgment and professionalism
• Experience supporting multiple executives with competing priorities
• Microsoft Office/Outlook required; Expensify, Asana, or Salesforce a plus

Why this role stands out:

• Up to $40/hour depending on experience
• Hybrid schedule
• Strong temp-to-hire potential with permanent compensation targeting $85K$90K
• Opportunity to build structure and make a lasting operational impact
• Mission-driven organization focused on educational equity and philanthropy
• High-touch partnership with collaborative, people-focused leadership

This is an excellent opportunity for someone who enjoys building order within growing organizations, loves being deeply embedded in executive operations, and takes pride in making leaders and teams more effective day to day.