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Director of Individual Insurance Compliance & Regulatory Affairs

Alera Group

Chicago, Illinois

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JOB DETAILS
SKILLS
Auditing, Best Practices, Business Operations, Communication Skills, Computer Security, Consumer Protection, Content Management Systems (CMS), Corrective Action, Cross-Functional, Documentation Standards, Federal Laws and Regulations, Financial Services, Healthcare, Insurance, Insurance Regulations, Leadership, Legal, Licensing, Maintain Compliance, Marketing, Medicare, Operational Support, Operations Processes, Problem Solving Skills, Process Management, Program Control, Regulations, Regulatory Compliance, Regulatory Requirements, Risk Analysis, Risk Management, Scalable System Development, State Laws and Regulations, Track Customer Issues
LOCATION
Chicago, Illinois
POSTED
5 days ago
OVERVIEW

Director of Individual Insurance Compliance & Regulatory AffairsAlera Group | Individual Insurance Segment
Alera Group is seeking a strategic and operationally focused compliance leader to oversee enterprise compliance and regulatory affairs across our growing Individual Insurance segment. This role will lead the development, implementation, and oversight of scalable compliance programs supporting Medicare Advantage, Medigap, Part D, ACA, and ancillary insurance products across a national distribution platform.

This is a highly visible leadership role responsible for strengthening regulatory governance, reducing enterprise risk, supporting audit readiness, and enabling sustainable growth through standardized and defensible compliance practices.

The ideal candidate brings deep expertise in Medicare and individual insurance compliance, strong regulatory knowledge, and experience building scalable compliance frameworks within complex, multi-site insurance or healthcare environments.

Why Join Alera Group
This is an opportunity to build and shape enterprise compliance strategy within a rapidly growing national organization. The Director of Individual Insurance Compliance & Regulatory Affairs will play a critical role in strengthening governance, enabling operational scalability, and supporting long-term growth across the Individual Insurance segment.

RESPONSIBILITIES

  • Lead enterprise compliance and ethics programs across all individual insurance product lines, including Medicare, ACA, Life, Dental, Vision, and supplemental products
  • Serve as the primary compliance leader for the Individual Insurance segment, partnering closely with executive leadership, Legal, Operations, Marketing, IT, and Carrier Relations
  • Monitor and interpret federal and state regulatory changes impacting Medicare and individual insurance products
  • Serve as primary contact for CMS-related compliance communications, audits, corrective actions, and regulatory inquiries
  • Develop and implement enterprise-wide compliance policies, standards, controls, and monitoring programs
  • Establish scalable compliance protocols aligned with regulatory requirements, carrier agreements, and operational best practices
  • Partner with business leaders and local agencies to identify compliance risks and implement corrective actions and remediation plans
  • Oversee compliance related to marketing, disclosures, consumer communications, consent requirements, and producer oversight
  • Lead compliance training, attestations, documentation standards, and audit readiness initiatives
  • Manage consumer complaint processes, investigations, and issue resolution efforts
  • Coordinate third-party audits, regulatory reviews, and compliance reporting activities
  • Partner with Legal and IT on privacy, data governance, and risk mitigation initiatives
  • Support integration and standardization efforts across a growing national platform
QUALIFICATIONS

  • 10+ years of compliance, regulatory affairs, risk management, or governance experience within insurance, healthcare, financial services, or related industries
  • Deep knowledge of Medicare Advantage, Part D, Medigap, ACA, and individual insurance regulatory environments
  • Strong understanding of CMS regulations, marketing guidelines, audit processes, and corrective action plans
  • Experience building and scaling compliance programs across decentralized or multi-site organizations
  • Proven success managing regulatory audits, investigations, remediation efforts, and operational compliance initiatives
  • Knowledge of state insurance regulations, licensing, and consumer protection requirements
  • Strong leadership, communication, and cross-functional partnership skills
  • Ability to translate complex regulatory requirements into practical operational processes and business controls
  • Bachelor's degree required; advanced degree or compliance-related certification preferred
ADDITIONAL INFORMATION

Compensation:
Salary range: $120,000 - $165,000 per year
Eligible for performance-based bonus: Yes

Benefits:
Alera Group offers comprehensive benefits including medical, dental, vision, life and disability coverage, 401(k), generous PTO, and more.

Work Model:
This role is Remote
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About the Company

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Alera Group