Senior Director, Compliance

The Aspen Group•Chicago, IL

19h•Hybrid

About The Position

The Aspen Group (TAG) is a leading retail healthcare business support organization in the U.S., supporting thousands of healthcare professionals and team members across numerous health and wellness offices. TAG provides centralized business support services to five consumer-facing businesses: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet Pet Health Care. This role is for a Senior Director, Compliance, responsible for leading TAG's Core Compliance function. The position involves building, scaling, and operating the enterprise healthcare compliance program across a large, multi-unit, geographically dispersed footprint. This role focuses on core healthcare regulatory compliance, working in partnership with Environmental Health & Safety, Licenses & Permits, and Privacy teams. The leader will build and sustain strong partnerships across various departments including Risk Management, Clinical, Operations, HR, Finance, IT, and Revenue Cycle. The role requires leading a high-performing Core Compliance team with clear accountability for results and serving as a credible communicator to stakeholders.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.
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.
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.
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.
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.
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.