Regulatory & Compliance Director Ryan Specialty Benefits (RSB)

Ryan Specialty

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profile Job Location:

Chicago, IL - USA

profile Yearly Salary: $ 172000 - 215000
Posted on: 15-10-2025
Vacancies: 1 Vacancy

Job Summary

Position Summary

The Regulatory & Compliance Director at Ryan Specialty Benefits (RSB) is responsible for leading and evolving the business units compliance program to ensure adherence to applicable federal and state regulations with a focus on self-funded medical stop-loss insurance and related operations. This role supports the organizations commitment to ethics regulatory integrity and operational excellence. The Director will collaborate closely with RSB leadership and Ryan Specialty Groups corporate legal and compliance teams to align business practices with enterprise-wide standards.

What will your job entail

Key Responsibilities

Regulatory Compliance & Risk Management

  • Lead the development implementation and oversight of compliance programs to ensure adherence to applicable laws and regulations including HIPAA ACA ERISA and state insurance department requirements.
  • Monitor regulatory developments impacting the stop-loss and self-funded benefits space and recommend necessary program enhancements.
  • Develop and maintain internal controls policies and procedures to mitigate compliance risk.
  • Conduct risk-based compliance testing and implement corrective actions to address noncompliance.
  • Support compliance readiness for carrier audits delegated authority reviews and post-audit remediation.

Program Development & Strategic Initiatives

  • Contribute to the strategic direction of RSBs compliance function including support for enterprise initiatives such as Program Ascend and technology transformation.
  • Collaborate with cross-functional teams (e.g. IT Controllership Operations) to embed compliance requirements into business processes and systems.
  • Conduct benchmarking and industry research to identify innovative practices and enhance program effectiveness.

Operational Collaboration

  • Maintain and update compliance documentation including policies standards and regulatory disclosures.
  • Serve as a liaison between RSB and Ryan Specialty Groups corporate legal and compliance teams to ensure alignment and consistency.
  • Support quality assurance efforts including underwriting file reviews and policy management oversight.

Qualifications

  • Bachelors degree in Risk Management Legal Studies Business or a related field.
  • 1215 years of experience in regulatory compliance preferably within the insurance industry with at least 5 years in a leadership role.
  • Strong knowledge of HIPAA ACA ERISA and insurance regulatory frameworks.
  • Experience drafting and implementing compliance documentation policies and procedures.
  • Demonstrated ability to lead compliance initiatives manage risk and influence cross-functional teams.
  • Excellent analytical organizational communication and interpersonal skills.
  • Familiarity with self-funded medical stop-loss insurance third-party administrator (TPA) relationships retail brokers and general agents is preferred.

Ryan Specialty is an Equal Opportunity Employer. We are committed to building and sustaining a diverse workforce throughout the vision is an inclusive and equitable workplace where all employees are valued for and evaluated on their performance and contributions. Differences in race creed color religious beliefs physical or mental capabilities gender identity or expressionsexual orientation and many other characteristics bring together varied perspectives and add value to the service we provide our clients trading partnersand policy extends to all aspects of our employment practices including but not limited to recruiting hiring discipline firing promoting transferring compensation benefits training leaves of absence and other terms conditions and benefits of employment.

How We Support Our Teammates

Ryan Specialty seeks to offer our employees a comprehensive and best-in-class benefits package that helps them and their family members achieve their physical financial and emotional well-being addition to paid time off for company holidays vacation sick and personal days Ryan offers paid parental leave mental health services and more.

The target salary range for this position is $172000.00 - $215000.00 annually.

The wage range for this role considers many factors such as training transferable skills work experience licensure and certification business needs and market demands. The pay range is subject to change and may be modified in the future. Full-time roles are eligible for bonuses and benefits. For additional information on Ryan Specialty Total Rewards visit our website provide individuals with disabilities reasonable accommodations to participate in the job application or interview process to perform essential job functions and to receive other benefits and privileges of employment in accordance with applicable law. Please contact us to request an accommodation at

The above is intended to describe this jobs general requirements. It is not to be construed as an exhaustive statement of duties responsibilities or physical requirements. Nothing in this job description restricts managements right to assign or reassign duties and responsibilities to this job at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.


Required Experience:

Director

Position SummaryThe Regulatory & Compliance Director at Ryan Specialty Benefits (RSB) is responsible for leading and evolving the business units compliance program to ensure adherence to applicable federal and state regulations with a focus on self-funded medical stop-loss insurance and related oper...
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Key Skills

  • Sales Experience
  • Microsoft Office
  • Customer Service
  • Communication skills
  • Microsoft Outlook
  • Microsoft Word
  • Business Management
  • Benefits Administration
  • Microsoft Excel
  • Insurance Sales
  • Customer relationship management
  • Human Resources