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 leadership in the Commercial Organization, including the Chief Commercial Officer (CCO). The CCO and other Commercial leaders have oversight over five distinct businesses, and we need an Executive Assistant who can keep pace with the constantly evolving Commercial org. 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.
- Strong written and verbal communication skills, including the ability to draft polished, professional correspondence.
- Ability to use discretion and handle sensitive or confidential information with the highest level of professionalism.
Salary: $85-105k
A generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match
Skills Required
- Bachelor's degree in business administration, communications, or a related field
- 8+ years of experience providing high-level administrative support
- 3-5 years of experience 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 effective prioritization
- Strong written and verbal communication skills
- Ability to handle sensitive or confidential information with discretion and professionalism
TAG - The Aspen Group Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about TAG - The Aspen Group and has not been reviewed or approved by TAG - The Aspen Group.
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Healthcare Strength — Multiple medical plan choices with defined costs, HSA support, and accessible plan documents indicate a robust health offering. Distinctive features like GLP‑1 coverage on the HSA plan and clear SBCs add clarity for election decisions.
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Retirement Support — A clearly outlined 401(k) program features an immediately vested employer match with explicit eligibility timing. Consistent references to the plan and enrollment resources across brand sites underscore ease of access.
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Affordable Benefits — Dental-care discounts through the Aspen Dental network—free preventive services and reduced rates for procedures—help lower out‑of‑pocket costs. Additional perks like brand discounts and pet insurance can further stretch total value for some roles.
TAG - The Aspen Group Insights
What We Do
When we helped launch Aspen Dental, we set out to break down the barriers that made it hard for patients to keep up with their dental health — affordability, transparency, and access. We knew the key to better patient care started with the provider, so we changed how the dental business worked. We built new relationships, expertise, and tools to help dentists run their businesses more effectively and better care for their patients. Fast forward, and over 25 years later, we support more than 1000 Aspen Dental locations—by doing so, we are proud to say we have changed access to dental care nationwide. But there’s more work to do. Healthier, happier smiles were just our beginning. We came together to launch TAG – The Aspen Group, officially expanding beyond dental and embracing a new vision. By bringing together Aspen Dental, Chapter, ClearChoice, WellNow, and Lovet into one family of brands, we set out to achieve one simple goal together: to bring better healthcare to more people - because we believe in a future where health and wellness is accessible for all. With that mission in mind, TAG now supports over 5,300 clinicians across more than 1,400 locations. While our vision is now broader, how we achieve it remains the same. The best care starts with the provider - and TAG exists to power them so they can meet patients where they are, no matter their specialty, and deliver better care. Because we know that at the end of the day, better healthcare is simple — empower the provider and their teams, and the rest will follow. United as one group, we’re not just breaking down barriers; today, we’re breaking through. We’re challenging the status quo. Together, we can prove healthcare can be better for both providers and patients. Together, we can bring better healthcare to more people.
Why Work With Us
TAG - The Aspen Group employs and/or supports over 25,000 healthcare professionals and team members at more than 1,400 health and wellness offices across 46 states in four distinct categories: Dental care, urgent care, medical aesthetics, and animal health. Every day we wake up to empower providers to do what they do best: focus on the patient.
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