
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 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, WellNowUrgent 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.
As a reflection of our current needs and planned growth we are very pleased to offer a new opportunity to join our dedicated team as a Senior Director, Compliance.
This leadership role leads TAG's Core Compliance function and is responsible for building, scaling, and operating the enterprise healthcare compliance program across a large, multi-unit, geographically dispersed footprint. TAG's broader compliance organization also includes dedicated Environmental Health & Safety, Licenses & Permits, and Privacy teams; this role focuses on core healthcare regulatory compliance. This leader builds and sustains strong partnerships across Risk Management, Clinical, Operations, HR, Finance, IT and Revenue Cycle leadership. Leads a high-performing Core Compliance team with clear accountability for results and services as a credible communicator to applicable stakeholders.
Compliance Program Execution
Operate TAG’s enterprise healthcare compliance program in alignment with OIG guidance, DOJ expectations, and applicable federal and state laws.
Drive day-to-day compliance with healthcare regulatory requirements, including HIPAA/HITECH, Medicare/Medicaid requirements, fraud and abuse laws (AKS, Stark), scope-of-practice rules, billing and coding standards, and corporate practice of medicine considerations.
Own enterprise compliance policies, procedures, standards of conduct, and internal controls across business units and clinical locations; refresh high-risk policies on a defined cadence.
Develop, deliver, and continuously improve compliance training and education programs for executives, clinicians, and staff, targeting high completion rates and meaningful knowledge transfer.
Lead compliance investigations, audits, and monitoring activities; ensure corrective action plans are timely, effective, and closed out with discipline, with measurable reduction in repeat findings year over year.
Support the Head of Risk and Compliance in managing government inquiries, audits, and regulatory examinations in coordination with the Legal Department.
Scaling Compliance Across Multi-Unit Healthcare
Design, build, and scale compliance programs, processes, and controls that operate consistently and effectively across 1,000+ locations, 46 states, and four clinical service lines, ensuring the program keeps pace with rapid organizational growth.
Build repeatable, technology-enabled workflows that allow the compliance program to grow with the business without linear headcount additions.
Standardize policies, training, monitoring, and remediation activities across business units while accommodating service line-specific regulatory nuances.
Build strong, trusted partnerships with operations and clinical leadership to embed compliance into field operations, new office openings, acquisitions, and integration activities.
Compliance Leadership & Team Performance
Lead and inspire the Core Compliance team, including directors, managers, specialists, and analysts; set a compelling vision, clear priorities, and high performance standards for the function.
Recruit, develop, coach, and retain top compliance talent; build clear career pathways, development plans, and succession depth across the team.
Establish and enforce a strong performance management culture with clear goals, measurable outcomes, regular feedback, and rigorous accountability for individual and team results.
Serve as a credible, polished executive presence with the General Counsel, Head of Risk and Compliance, and other senior-level audiences; communicate complex compliance matters with clarity, confidence, and strategic context.
Proactive, Data-Driven Compliance
Drive TAG’s shift from a reactive to a proactive, predictive compliance posture — identifying and addressing risk before issues escalate.
Use data, analytics, and key risk indicators (KRIs) to identify trends, hot spots, and emerging compliance risks across business units and geographies.
Embed compliance early in strategic initiatives, M&A activity, new market entry, new service line launches, and office openings/closures.
Continuously evaluate program maturity against DOJ/OIG expectations and industry leading practices; drive a forward-looking roadmap of program enhancements.
Champion a prevention-first, transformation-oriented mindset across the organization, designing controls, training, and monitoring that stop issues from occurring, not just detect them after the fact.
Analytics, Scorecarding & Executive Reporting
Design, launch, and operate executive-level Compliance KPI dashboards, scorecards, and key risk indicators that translate program activity into clear, decision-ready insights.
Apply strong analytical skills to source, structure, and interpret compliance data from across the enterprise, turning raw signals into trends, themes, and recommended actions.
Build the underlying data architecture, metrics definitions, and reporting cadence required to make scorecards reliable, repeatable, and trusted.
Deliver executive-level presentations and reports to the Head of Risk and Compliance, General Counsel, and other senior leaders; tailor messaging to drive informed decision-making.
Partner with technology and analytics teams to automate compliance reporting, reduce manual effort, and accelerate insight generation.
Monitoring, Auditing & Audit Readiness
Design and execute the enterprise compliance auditing and monitoring work plan, including risk-based audits across coding/billing, clinical documentation, HIPAA, and operational compliance.
Establish centralized audit tracking, with clear ownership, due dates, and disciplined closure of findings.
Lead execution of mock regulatory audits and readiness exercises to stress-test the compliance program before regulators do.
Drive year-over-year reduction in audit findings and repeat findings through systemic root-cause remediation.
Partnership with Risk Management
Build and maintain a strong, collaborative partnership with the Risk Management team to deliver an integrated, well-coordinated compliance and risk program.
Align compliance monitoring, investigations, and remediation activities with enterprise risk activities led by the Risk Management team.
Share compliance data, trends, and key risk indicators with the Risk Management team to support enterprise-wide visibility and decision-making.
Controlled Substances & Clinical Compliance
Operate compliance activities related to controlled substances, including DEA, state pharmacy, and controlled substance regulations, covering ordering, storage, prescribing, dispensing, inventory control, disposal, and diversion prevention.
Lead HIPAA compliance activities, ensuring enterprise-wide adherence to HIPAA/HITECH requirements across all business units and clinical locations.
Partner with clinical and quality leaders on compliance aspects of patient safety, infection control, and quality improvement initiatives.
Coordinate responses to regulatory inspections, surveys, and enforcement actions, escalating to the Head of Risk and Compliance and Legal as appropriate.
Governance & Speak-Up Culture
Serve as a key advisor to the Vice President and Head of Risk and Compliance, General Counsel on compliance matters.
Foster a culture of compliance, accountability, and continuous improvement throughout the organization.
Champion a “speak up” culture; ensure the compliance hotline, intake, triage, and investigation processes are trusted, accessible, and effective, with zero tolerance for retaliation.
Drive employee awareness of reporting channels and a healthy reporting volume as a leading indicator of program trust.
Represent Compliance in cross-functional governance forums and executive committees.
Requirements/Qualifications:
Bachelor’s degree required with a preferred advanced degree (Juris Doctor, Master’s, or Doctorate); healthcare related field strongly preferred.
Equivalent combination of education, training, and relevant experience will also be considered.
Minimum of 10 to 12 years of progressive experience in healthcare compliance, with significant time in leadership roles.
Proven experience leading, building, and scaling compliance programs in large, multi-unit, geographically dispersed healthcare organizations through periods of growth and transformation.
Demonstrated ability to build, develop, and retain high-performing teams; strong track record of performance management, accountability, and driving measurable team results.
Strong analytical skills with hands-on experience designing and operating compliance KPIs, scorecards, dashboards, and key risk indicators.
Exceptional executive-level written, verbal, and presentation skills, with demonstrated experience presenting complex compliance matters to senior audiences with clarity and strategic impact.
Strong working knowledge of federal and state healthcare laws and regulatory enforcement trends, including HIPAA/HITECH, AKS, Stark, and Medicare/Medicaid requirements.
Demonstrated experience managing complex compliance audits, investigations, and remediation activities.
Proven ability to build strong cross-functional partnerships and influence senior business and clinical leaders to embed compliance into operational decision-making.
Preferred Qualifications:
Experience in physician practice management, outpatient services, or other distributed healthcare delivery models.
Compliance certification (e.g., CHC, CCEP, or equivalent).
Experience preparing materials for and presenting to Boards or Board-level committees.
Familiarity with private equity-backed or high-growth healthcare organizations.
Experience transforming compliance programs from reactive to proactive, data-driven operating models; track record of driving cultural and operational change.
Strong, decisive, and visionary leader who sets direction, develops talent, holds the team accountable, and drives sustained high performance.
Proactive, transformation-driven mindset; anticipates issues, challenges the status quo, and drives continuous program improvement rather than reacting to problems.
Strong analytical orientation, comfortable with data, metrics, KPIs, and translating numbers into narrative.
Pragmatic, creative problem solver who can break down complex, ambiguous issues, identify root causes, and deliver scalable, sustainable solutions across a multi-unit healthcare environment.
Builder mindset, proven ability to scale programs, processes, and teams across a high-growth, multi-unit healthcare organization.
Trusted partner and relationship builder; earns credibility across clinical, operational, and corporate functions and drives alignment through influence rather than authority.
Executive presence and polished communicator; distills complex compliance issues into clear, actionable insights for C-suite and Board audiences.
High accountability orientation; owns outcomes, holds self and team to commitments, manages performance with discipline, and closes the loop on every deliverable.
Strong judgment, ethical decision-making, and ability to balance regulatory rigor with operational realities.
High degree of discretion, professionalism, and integrity.
Base Pay Range: $209,800 - $250,000, plus 25% annual bonus (Actual pay may vary based on experience, performance, and qualifications.)
A generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match.
The position is based in Chicago, IL, with an expectation of 4 days per week in-office and 1 day remote. Candidates located outside the 35-mile radius of Chicago may be considered, for remote, on a case-by-case basis.
If you are an applicant residing in California, please view our privacy policy here: https://careers.aspendental.com/us/en/tag-privacy-policy-for-california-employees

When we launched 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’ve launched 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 come together to launch TAG – The Aspen Group, and we are officially expanding beyond dental to embrace a new vision. As we transform Aspen Dental, Chapter, ClearChoice, WellNow, and Lovet into one family, we’re setting 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. While our vision now is 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.