Strategic Executive Assistant to Senior Leadership

Wellnow; Chicago (IL); On-site; USD 85,000 - 100,000; Full time

Benefits offered by this job

Paid time off

Health insurance

Dental insurance

Vision insurance

401(k) with match

Job summary

The Aspen Group (TAG) is seeking an organized Executive Assistant to support senior Field leadership from our Chicago headquarters. You will manage calendars, coordinate complex travel, and craft professional communications while ensuring seamless operations across executive functions.

Ideal candidates bring 8+ years of administrative experience, strong business acumen, and discretion. This role supports board-related preparations and high-level events, with a focus on strategic alignment and

Qualifications

• 8+ years of high-level administrative support, including executive support.
• Experience coordinating executive travel domestically and internationally.
• Strong organizational and multitasking abilities with attention to detail.

Responsibilities

• Serve as primary liaison between senior leadership and internal/external stakeholders.
• Manage dynamic executive calendars and complex travel arrangements.
• Draft polished communications and prepare internal/external reports and presentations.
• Support board meetings, executive retreats, and high-level events, ensuring materials and logistics are ready.

Skills

Executive support

Calendar management

Travel coordination

Communication skills

Discretion

Education

Bachelor’s degree in business/communications

Tools

MS Office

Teams

Google Meet

Job description

The Aspen Group (TAG) is seeking an organized Executive Assistant to support senior Field leadership from our Chicago headquarters. You will manage calendars, coordinate complex travel, and craft professional communications while ensuring seamless operations across executive functions.

Ideal candidates bring 8+ years of administrative experience, strong business acumen, and discretion. This role supports board-related preparations and high-level events, with a focus on strategic alignment and