Executive Assistant - Field Operations

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 one of the largest and most trusted retail healthcare business support organizations in the U.S. and has supported over 20,000 healthcare professionals and team members at more than 1,300 health and wellness offices across 48 states in four distinct categories: dental care, urgent care, medical aesthetics, and animal health. Working in partnership with independent practice owners and clinicians, the team is united by a single purpose: to prove that healthcare can be better and smarter for everyone. TAG provides a comprehensive suite of centralized business support services that power the impact of five consumer-facing businesses: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet Pet Health Care. Each brand has access to a deep community of experts, tools and resources to grow their practices, and an unwavering commitment to delivering high-quality consumer healthcare experiences at scale.

We are seeking a highly organized and proactive Executive Assistant to provide dedicated support to senior Field leadership at Aspen Dental. Based at our corporate headquarters in Chicago, this role is critical in managing complex schedules, streamlining communication, and ensuring the seamless operation of executive functions both within and beyond the office. As a strategic partner to senior leaders, you will plan capacity, prioritize competing demands, and keep the executive focused on the work that moves the business forward. The ideal candidate has impeccable attention to detail and sound judgment, and is resourceful and proactive in anticipating the needs of executives. The ideal candidate will bring strong business acumen and an understanding of how the organization works, and can connect day-to-day priorities to larger company goals.

Essential Responsibilities:

• Serve as the primary liaison between senior leadership and internal teams or external stakeholders.
• Manage several dynamic executive calendars, ensuring all logistical details are handled seamlessly.
• Think strategically: anticipate the executive’s needs, connect daily work to business priorities, and flag risks and opportunities early.
• Plan capacity and manage the executive’s time and workload so effort goes to the highest-value priorities.
• Apply strong business acumen to understand how the company operates, prioritize requests, and make informed decisions.
• Plan and manage comprehensive travel arrangements, including flights, accommodations, transportation, and itineraries. Maintain accurate records of travel schedules and preferences to streamline future planning.
• Draft professional, polished communication for various audiences on behalf of senior leadership when appropriate.
• Assist in preparing internal and external reports, presentations, and other business documents, ensuring clarity, grammatical accuracy, and alignment with organizational branding.
• Process accurate and timely expense reports. Monitor expenses and liaise with finance teams to ensure policy compliance and resolve discrepancies when necessary.
• Provide administrative support for special projects, including planning, coordination, and follow-up on deliverables.
• Assist with preparation for board meetings, executive retreats, and other high-level events, ensuring all materials are ready and logistical details are confirmed.
• Anticipate challenges and identify creative solutions. Address urgent issues or requests from senior leadership with a resourceful, solutions-oriented approach.

Requirements / Qualifications:

Education

• Bachelor’s degree in business administration, communications, or a related field preferred.

Experience

• 8+ years of experience providing high-level administrative support, including at least 3–5 years supporting executives or senior leadership.
• Experience coordinating executive-level travel, both domestic and international.
• Experience working in a corporate, complex, or dynamic organization is a plus.

Knowledge & Skills

• Knowledge of basic financial processes, such as preparing expense reports and managing budgets.
• Advanced proficiency with the Microsoft Office Suite and collaboration tools (e.g., Teams, Google Meet).
• Exceptional organizational and multitasking skills, with the ability to prioritize effectively.
• Anticipates needs and solves problems before they
• Stays calm and flexible in a fast-moving environment.
• Strong attention to detail with a high bar for quality and accuracy
• Strong written and verbal communication skills, including the ability to draft polished, professional correspondence.
• Ability to build trust by using discretion and handling sensitive or confidential information with the highest level of professionalism.

Salary: $85-100k

A generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match