Executive Assistant

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Executive Assistant — Administrative Operations (On-Site | Chicago)

A fast-growing, technology-driven organization headquartered in Chicago is seeking a highly capable Administrative Assistant to support senior leadership and executive operations. This role is ideal for someone who thrives in a high-energy environment, anticipates needs before they arise, and enjoys bringing structure, clarity, and momentum to complex organizations.

You will work closely with executive leadership to keep day-to-day operations running smoothly while supporting key initiatives that impact the broader business.

• Maintain and manage complex executive calendars, schedules, and priorities
• Act as a proactive gatekeeper—anticipating issues and resolving them before they escalates
• Support daily operations by creating structure, rhythm, and follow-through across initiatives
• Monitor and manage email correspondence; draft internal communications and updates
• Prepare materials, summaries, and reporting to support leadership decision-making
• Track action items from meetings and ensure timely follow-up across stakeholders
• Coordinate domestic and international travel arrangements as needed
• Partner cross-functionally to streamline workflows and improve operational efficiency
• Assist with high-priority projects and help drive them to completion
• Contribute to building scalable processes that create leverage for leadership and teams

• 5+ years of experience supporting senior or executive-level leaders
• Proven success managing complex calendars and competing priorities
• Exceptionally organized, detail-oriented, and proactive by nature
• Comfortable working with different leadership styles, personalities, and cultures
• Strong written and verbal communication skills
• Calm under pressure with the ability to think quickly and independently
• Advanced proficiency with Microsoft Office (Outlook, Word, Excel, PowerPoint)
• Experience supporting fast-paced, tech-enabled or SaaS environments strongly preferred

• Direct exposure to executive leadership and strategic initiatives
• High visibility and impact within a growing organization
• Opportunity to help shape processes, not just follow them
• Collaborative, high-performance culture with room to grow

Mid-Senior level

Full-time

Administrative

Industries:
Software Development

• Medical insurance
• Paid paternity leave
• Tuition assistance
• Disability insurance
• Child care support
• Vision insurance
• 401(k)
• Paid maternity leave
• Student loan assistance