Executive Assistant - Field Operations

TAG - The Aspen Group•Chicago, IL

1d•$85,000 - $100,000•Onsite

About The Position

The Aspen Group (TAG) is a retail healthcare business support organization serving healthcare professionals and team members across dental care, urgent care, medical aesthetics, and animal health. TAG provides centralized business support services to Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet Pet Health Care. The Executive Assistant provides dedicated support to senior Field leadership at Aspen Dental and is based at the company’s corporate headquarters in Chicago. The role manages complex schedules, streamlines communication, and supports the smooth operation of executive functions within and beyond the office. Acting as a strategic partner to senior leaders, the Executive Assistant plans capacity, prioritizes competing demands, and helps focus executive time on high-value work. The position calls for attention to detail, sound judgment, resourcefulness, proactive anticipation of executive needs, business acumen, and the ability to connect daily priorities to broader company goals.

Requirements

At least 8 years of experience providing high-level administrative support, including at least 3–5 years supporting executives or senior leadership.
Experience coordinating executive-level domestic and international travel.
Knowledge of basic financial processes, such as preparing expense reports and managing budgets.
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.
Ability to anticipate needs and solve problems before they escalate.
Ability to remain calm and flexible in a fast-moving environment.
Strong attention to detail and commitment to quality and accuracy.
Strong written and verbal communication skills, including the ability to draft polished, professional correspondence.
Ability to build trust through discretion and professional handling of sensitive or confidential information.

Nice To Haves

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

Responsibilities

Serve as the primary liaison between senior leadership and internal teams or external stakeholders.
Manage several dynamic executive calendars and handle associated logistical details.
Anticipate executive needs, connect daily work to business priorities, and flag risks and opportunities early.
Plan capacity and manage executive time and workload to prioritize high-value work.
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 accurate travel records and preferences.
Draft professional communications for various audiences 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 promptly; monitor expenses and work with finance teams on policy compliance and discrepancies.
Provide administrative support for special projects, including planning, coordination, and follow-up on deliverables.
Prepare for board meetings, executive retreats, and other high-level events, including materials and logistics.
Anticipate challenges, identify creative solutions, and respond resourcefully to urgent leadership issues or requests.