Executive Assistant - Commercial Organization

TAG - The Aspen Group•Chicago, IL

1d•$85,000 - $105,000•Onsite

About The Position

The Aspen Group (TAG) is a retail healthcare business support organization serving more than 20,000 healthcare professionals and team members at over 1,300 offices across 48 states. It supports five consumer-facing healthcare businesses across dental care, urgent care, medical aesthetics, and animal health. TAG is seeking a highly organized, proactive Executive Assistant to provide dedicated support to senior leadership in the Commercial Organization, including the Chief Commercial Officer. Based at the corporate headquarters in Chicago, the role manages complex schedules, communication, and executive functions. As a strategic partner, the Executive Assistant plans capacity, prioritizes competing demands, and connects daily priorities to broader company goals.

Requirements

At least 8 years of experience providing high-level administrative support, including 3–5 years supporting executives or senior leadership.
Experience coordinating executive-level domestic and international travel.
Knowledge of basic financial processes, including expense reports and budget management.
Advanced proficiency with Microsoft Office Suite and collaboration tools such as Teams and Google Meet.
Exceptional organizational and multitasking skills, with the ability to prioritize effectively.
Strong written and verbal communication skills, including the ability to draft polished professional correspondence.
Ability to use discretion and handle sensitive or confidential information professionally.

Nice To Haves

Bachelor’s degree in business administration, communications, or a related field.
Experience working in a corporate, complex, or dynamic organization.

Responsibilities

Serve as the primary liaison between senior leadership and internal teams or external stakeholders.
Manage several dynamic executive calendars and ensure logistical details are handled.
Anticipate executive needs, connect daily work to business priorities, and flag risks and opportunities.
Plan capacity and manage executive time and workload to focus on high-value priorities.
Apply business acumen to understand company operations, prioritize requests, and make informed decisions.
Plan and manage domestic and international travel arrangements, including flights, accommodations, transportation, and itineraries; maintain travel schedules and preferences.
Draft professional communications on behalf of senior leadership when appropriate.
Assist with internal and external reports, presentations, and business documents, ensuring clarity, grammatical accuracy, and alignment with organizational branding.
Process expense reports accurately and on time; monitor expenses, coordinate with finance teams, and resolve discrepancies.
Provide administrative support for special projects, including planning, coordination, and follow-up on deliverables.
Assist with board meetings, executive retreats, and other high-level events, preparing materials and confirming logistics.
Anticipate challenges, identify creative solutions, and respond resourcefully to urgent leadership requests.