Executive Assistant for AI Startup
Budget: $25 – $50 USD
Who We Are and What We Need:
We are a fast-moving AI startup based in Chicago seeking an Executive Assistant to support our CEO on an urgent, short-term contract with the potential to convert to full-time. This role goes beyond traditional admin work you’ll help manage priorities, keep workflows organized across tools like ClickUp or Notion, coordinate follow-ups, and support cross-functional projects in a dynamic startup environment. We’re looking for someone highly organized, proactive, and adaptable who can step in immediately to provide structure and operational support. Preference for Chicago-based candidates who can join us in our Fulton Market office, though flexibility is possible.
What You’ll Do Organization & Productivity:
• Manage calendars priorities and workflows to maximize CEO effectiveness.
• Implement and manage productivity tools such as Jira ClickUp and others to track tasks and projects.
• Ensure deadlines and follow ups are clearly owned and executed across teams. Cross Functional Collaboration
• Act as a connective tissue between CEO and other departments ensuring clear communication and alignment.
• Support preparation for key meetings investor conversations and strategic planning sessions.
• Document and track action items ensuring accountability across stakeholders.
Why Join Us:
• Direct exposure to the CEO and firsthand experience in startup building.
• Competitive compensation with above market equity opportunities.
• Flexible arrangement full time hire or three month contract to hire.
• Brand new office in Chicago’s Fulton Market collaborative high energy environment.
• Opportunity to shape the operational foundation of a transformative AI company.
We are a fast-moving AI startup based in Chicago seeking an Executive Assistant to support our CEO on an urgent, short-term contract with the potential to convert to full-time. This role goes beyond traditional admin work you’ll help manage priorities, keep workflows organized across tools like ClickUp or Notion, coordinate follow-ups, and support cross-functional projects in a dynamic startup environment. We’re looking for someone highly organized, proactive, and adaptable who can step in immediately to provide structure and operational support. Preference for Chicago-based candidates who can join us in our Fulton Market office, though flexibility is possible.
What You’ll Do Organization & Productivity:
• Manage calendars priorities and workflows to maximize CEO effectiveness.
• Implement and manage productivity tools such as Jira ClickUp and others to track tasks and projects.
• Ensure deadlines and follow ups are clearly owned and executed across teams. Cross Functional Collaboration
• Act as a connective tissue between CEO and other departments ensuring clear communication and alignment.
• Support preparation for key meetings investor conversations and strategic planning sessions.
• Document and track action items ensuring accountability across stakeholders.
Why Join Us:
• Direct exposure to the CEO and firsthand experience in startup building.
• Competitive compensation with above market equity opportunities.
• Flexible arrangement full time hire or three month contract to hire.
• Brand new office in Chicago’s Fulton Market collaborative high energy environment.
• Opportunity to shape the operational foundation of a transformative AI company.