Director, Learning and Development, Aspen Field Leaders, Operations, Scheduling Center + Multi-Brand Development (Chicago)

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 team at Aspen Dental as a Director, Learning and Development, Aspen Field Leaders, Operations, Scheduling Center + Multi-Brand Development.Job SummaryThe Director of Learning & Development for Aspen Dental Field Leaders, Operations, Scheduling Center, and Multi-Brand Development is a key leader within the L&D team, responsible for shaping and executing learning strategies that build capability, consistency, and performance.Reporting to the Vice President of L&D, this role partners closely with senior leaders across Field Operations, Scheduling Center, HR, and brand leadership teams to design and deliver impactful learning solutions for non-clinical team members at all levels—from patient-facing roles to senior field leadership.This leader brings strong business acumen and deep expertise in performance consulting, translating complex business needs into scalable, high-impact learning strategies. They operate effectively in a multi-brand, matrixed environment—balancing enterprise alignment with brand-specific needs—while leveraging data to drive decisions and demonstrate measurable business impact. This role requires both strategic leadership and a hands-on approach to building and delivering solutions.Essential Responsibilities:Strategy & AlignmentDevelop and execute a comprehensive learning strategy across Field Leadership, Operations, Scheduling Center, and multi-brand teams, aligned to enterprise and brand-specific business goals.Partner with senior leaders across Aspen Dental and TAG brands to identify capability gaps and define development priorities.Ensure alignment and integration of learning strategies across brands while allowing for customization based on unique business needs.Leadership & CultureDrive a culture of continuous learning and development across field, operations, scheduling center and TAG multiple brand environments.Lead and develop a team of L&D professionals, fostering high performance, collaboration, and growth.Act as a visible champion for talent development across Aspen Dental and other brands.Program Design & DeliveryDesign and deliver a portfolio of learning solutions—including formal programs, digital learning, coaching, and experiential development—that build operational excellence, leadership capability, and performance.Oversee role-based development strategies for field leaders (OM, RM, TD, DVP), operations teams, and Scheduling Center roles (agents through leadership).Ensure learning solutions are scalable, consistent, and aligned with broader enterprise initiatives.Measurement & Continuous ImprovementEvaluate existing programs and content for effectiveness, scalability, and alignment with business needs.Leverage data and analytics to measure impact, identify trends, and continuously improve learning solutions.Provide insights and recommendations to senior leaders to inform talent and business strategies.Collaboration & InfluenceServe as a trusted advisor to senior leaders across Field Operations, Scheduling Center, HR, and brand leadership teams.Partner cross-functionally to solve business challenges and contribute L&D expertise to enterprise initiatives.Ensure learning programs are effectively integrated across clinical and non-clinical teams where appropriate.Requirements/Qualifications:Education Level: Bachelor’s degree required; Master’s degree preferred.A minimum of 7+ years of relevant learning and development experience, ideally in a fast-paced organization with a distributed workforce.A minimum of 5+ years leading a team of L&D professionals.Advanced understanding of adult learning theory and principles.Understanding of DSOs (dentistry service organizations) or similar medical industries is desirable.Strong business insight, with the ability to credibly make a business case, by linking current and anticipated business challenges with learning and development solutions.Well versed in digital learning, just-in-time / micro-learning, and blended learning strategies.Strong capabilities in data analytics (as it pertains to measuring learning).Experience providing consultation to senior leadership on strategic initiatives.Excellent communication and influencing skills at all levels of the organization and extremely flexible to be proactive in a fast-paced, ever-changing environment.Excellent facilitation and mentoring skills. Experience in group facilitation and leading group/cohort dynamics to create connections and foster understanding.Ability to travel as needed.Salary Range $153,000 - $180,000 DOE with 25% bonusSummaryLocation: Chicago, Illinois; Remote, New YorkType: Full time