Facilitator, Orientation & Leadership Development

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 with close to 1,500 health and wellness offices across 50 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 AZPetVet. 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.

As a reflection of our current needs and planned growth we are very pleased to offer a new opportunity to join our dedicated L&D team at TAG as a Facilitator, Orientation & Leadership Development.

Job Summary:

The Facilitator, Orientation & Leadership Development is part of the Learning & Development team and is responsible for facilitating engaging, high-impact learning experiences across new hire orientation and leadership development programs. This role helps create a consistent, welcoming, and brand-aligned experience for employees joining the organization, while also supporting learners at all levels in building leadership capability.

The Facilitator brings learning experiences to life by creating an inclusive environment, connecting content to business priorities, and helping participants apply concepts to their roles. This role also supports the continued evolution of the orientation experience by gathering feedback, identifying opportunities for improvement, and partnering with stakeholders across Learning & Development and the business.

The ideal candidate is an engaging facilitator, strong communicator, highly organized, and passionate about creating meaningful learning experiences and positive first impressions that reflect the company’s culture, values, and brand.

This role reports to the Director, Leadership Development & Coaching, Orientation, Learning Experience, and is based in our learning facility in Chicago, IL.

Essential Responsibilities:

• Own and facilitate new hire orientation in classroom, virtual, and classroom studio formats, ensuring a welcoming, consistent, and high-quality experience for all new employees.
• Serve as one of the first representatives of the company for new hires, modeling the organization's values, culture, and brand experience.
• Facilitate leadership development programs for learners at all levels.
• Use strong facilitation techniques to bring content to life and help learners connect concepts and skills to their roles.
• Facilitate effectively across modalities, including in-person, virtual, and classroom studio environments.
• Use virtual facilitation tools and classroom technology to sustain learner engagement, manage participation, and troubleshoot learner technology needs during sessions.
• Handle challenging questions or discussions with composure, professionalism, and appropriate redirection.
• Stay current on business initiatives, brand priorities, and organizational changes to ensure orientation and learning experiences remain relevant.
• Gather participant and stakeholder feedback to identify ways to improve the orientation experience.
• Own updates, enhancements, and continuous improvement efforts for orientation.
• Assist with needs analysis, learning design, program development, and evaluation as needed.
• Collaborate with internal stakeholders, subject matter experts, vendors, and other members of the L&D organization.
• Plan, organize and execute tasks and activities with urgency and attention to detail.
• Other duties as assigned.

Requirements/Qualifications:

• 2+ years of experience facilitating in-person and virtual learning experiences in corporate L&D, education, onboarding, training, or a related professional setting.
• Strong facilitation skills with experience engaging small and large groups across multiple formats.
• Passion for creating a positive first impression and delivering a welcoming, brand-aligned experience for new employees.
• Experience facilitating leadership development programs or content.
• Experience owning program updates, process improvements, or learning experience enhancements.
• Knowledge of adult learning principles and learner engagement strategies.
• Excellent verbal and written communication skills.
• Strong listening skills with the ability to draw connections between learner needs, business priorities, and learning content.
• Strong presence, composure, and ability to think on your feet during live sessions.
• Ability to manage time, pacing, logistics, and participant needs in a fast-paced learning environment.
• Strong organizational skills and high attention to detail.
• Ability to work effectively with multiple internal and external stakeholders, including subject matter experts and business partners.
• Flexibility and agility to manage ambiguity, adapt to change, and remain effective in an evolving environment.
• Proficiency with Microsoft Office Suite, including Outlook, Word, Excel, PowerPoint, and SharePoint.
• Advanced proficiency using Zoom, including managing breakout rooms, chat, polls, screen sharing, and participant engagement during virtual sessions.
• Ability to travel as needed.
• Role is based in Chicago

Salary Range: $85,000 ~ $90,000