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Director of Individual Insurance Compliance & Regulatory Affairs

Alera Group

Chicago, Illinois

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JOB DETAILS
SKILLS
Analysis Skills, Centers for Medicare and Medicaid Services (CMS), Communication Skills, Consumer Protection, Content Management Systems (CMS), Corrective Action, Cross-Functional, Documentation, Documentation Standards, Federal Laws and Regulations, Financial Services, Health Insurance, Healthcare, Insurance, Insurance Regulations, Leadership, Legal, Maintain Compliance, Marketing, Medicare, Operational Strategy, Problem Solving Skills, Regulations, Regulatory Compliance, Regulatory Submissions, Retail Operations, Risk, Risk Analysis, Risk Management, Scalable System Development, Standards Development, State Laws and Regulations, Team Player, Time Management, Training Program, Training/Teaching, Vision Plan, Wholesale Industry
LOCATION
Chicago, Illinois
POSTED
2 days ago
OVERVIEW

Director of Individual Insurance Compliance & Regulatory Affairs
Individual Insurance Segment - Remote
About the Role
Alera Group is seeking a Director of Individual Insurance Compliance & Regulatory Affairs to lead and strengthen enterprise-wide compliance strategy across our Individual Insurance Segment. This senior leadership role is responsible for building scalable, defensible compliance frameworks that support growth while ensuring regulatory excellence across Medicare, ACA, and ancillary insurance products.

Reporting directly to the Chief Legal Officer with a dotted-line partnership to the SVP of Strategy & Operations, this role will collaborate across Legal, Operations, Marketing, IT, Carrier Relations, and agency leadership to drive consistency, accountability, and audit readiness throughout the organization.
Why Alera Group
Meaningful Impact: Help shape the compliance foundation supporting millions of healthcare and insurance interactions while protecting clients, consumers, and the organization.

Growth & Learning: Join a fast-growing national organization where you'll influence enterprise strategy, operational transformation, and long-term scalability.

Collaborative Culture: Work alongside Legal, Operations, Strategy and Compliance in a highly collaborative and mission-driven environment.

RESPONSIBILITIES

What You'll Do
  • Lead compliance and ethics programs across Medicare Advantage, Medigap, PDP, ACA, Life, Dental, Vision, and supplemental insurance products
  • Develop and implement enterprise-wide compliance policies, standards, and procedures
  • Monitor federal and state regulatory changes and ensure timely operational implementation
  • Serve as the primary contact for CMS-related audits, communications, and corrective actions
  • Partner with agency leadership to identify compliance risks and implement remediation strategies
  • Oversee compliance monitoring activities across wholesale and retail operations
  • Manage marketing compliance, regulatory disclosures, filings, and consent requirements
  • Design and deliver compliance training, attestations, and education programs
  • Lead consumer complaint management and corrective action processes
  • Develop standardized compliance language, agent agreements, and documentation practices
  • Coordinate third-party audits, regulatory reviews, and compliance assessments
  • Partner with Legal, IT, and Risk teams on privacy, ethics, and breach response initiatives
  • Drive consistency and standardization across the Individual Insurance Segment
QUALIFICATIONS

What You Bring
  • Extensive experience leading compliance programs within the insurance, healthcare, financial services, or regulated industries
  • Strong working knowledge of Medicare, ACA, CMS regulations, and state insurance compliance requirements
  • Experience supporting enterprise or multi-location operations with scalable compliance frameworks
  • Proven ability to lead regulatory audits, corrective actions, and risk mitigation initiatives
  • Strong understanding of compliance governance, documentation standards, and operational controls
  • Excellent communication, collaboration, and stakeholder management skills
  • Ability to influence senior leadership and drive enterprise-wide alignment
  • Strong analytical and problem-solving capabilities with a proactive mindset
  • Experience partnering cross-functionally with Legal, Operations, IT, Marketing, and executive leadership teams
What Sets You Up for Success
  • Strong audit outcomes and regulatory readiness
  • Reduced compliance incidents and repeat findings
  • Timely implementation of changing regulatory requirements
  • Standardized compliance processes and documentation across agencies
  • High completion and engagement rates for training and attestation programs
  • Scalable compliance practices that support organizational growth
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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Alera Group