Executive Assistant Lead
Job in
Chicago, Cook County, Illinois, 60290, USA
Listed on 2026-02-28
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
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.
EXECUTIVESUPPORT
- 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.
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.
- 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.
- 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.
- 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.
- 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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