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Executive Assistant Lead

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Leo Chicago
Full Time position
Listed on 2026-02-28
Job specializations:
  • Management
    Business Administration, Employee Relations, Administrative Management
  • Administrative/Clerical
    Business Administration, Employee Relations, Administrative Management
Salary/Wage Range or Industry Benchmark: 60000 - 80000 USD Yearly USD 60000.00 80000.00 YEAR
Job Description & How to Apply Below

We’re looking for a highly strategic, proactive and collaborative Executive Assistant Lead to support our CEO and Head of Operations. They will also be responsible for overseeing the Executive + Administrative Assistant (EA/AA) team. This role blends elevated executive support with team leadership, operational excellence, and cultural stewardship, ensuring lead team is supported holistically, the department operates smoothly, and people feel connected, informed and empowered.

EXECUTIVE

SUPPORT
  • Serve as a trusted partner to the CEO + HoOs, managing complex calendars, priorities and communications with professionalism and discretion.
  • Anticipate needs, streamline workflows and create structure that enables focus on high-impact work.
  • Facilitate clear communication across internal and external stakeholders.
EA

TEAM LEADER SHIP & PERFORMANCE MANAGEMENT
  • Lead, mentor, and manage the Executive/Administrative Assistant team, fostering collaboration, accountability, and operational excellence.
  • Oversee staffing, workload balance, development planning, and performance conversations for EA + AA team members.
  • Build team standards, best practices, and scalable systems to support executives consistently and effectively.
EA STRUCTURE AND PROCESS OPTIMIZATION
  • Identify opportunities to improve administrative workflows, communication pathways, and cross-team alignment, creating a consistent support approach for all leadership.
  • Design and implement processes that support agency efficiency and reduce friction.
  • Partner with Operations, HR, and other internal teams to ensure seamless integration of new tools, procedures, and expectations.
CULTURE, OFFICE AND EVENTS
  • Support onsite office experience, ensuring a welcoming, organized, and energizing environment for employees and visitors.
  • Partner on culture-building initiatives, internal events, leadership meetings, and agency-wide moments that strengthen community and connection.
  • Serve as a visible, approachable ambassador of the agency culture.
QUALIFICATIONS
  • 7+ years of Executive Assistant experience, with at least 2 years supporting C-suite leaders; agency or creative-industry experience preferred.
  • Experience leading or managing teams, with proven success in coaching, performance management, and talent development.
  • Strong business judgment, communication skills, and emotional intelligence.
  • Exceptional organizational ability with a talent for building structure in fast-moving, ambiguous environments.
  • Skilled in process improvement, operations, and cross-functional collaboration.
  • High degree of professionalism, discretion, and resilience.
  • Passion for culture, creativity, and the power of a well-run organization.
WHAT YOU’LL BRING
  • A mix of strategic thinking and flawless execution.
  • A solutions-first mindset.
  • A desire to help people do their best work.
  • And a genuine love of building the connective tissue that helps an agency thrive.
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