[Hiring] Vice President, Insurance Compliance @The Lightstone Group, LLC

Role Description

Lightstone is seeking an experienced VP or SVP of Insurance Compliance to manage regulatory compliance across its growing multi-entity insurance and reinsurance group. Reporting to senior leadership, this individual will be responsible for the day-to-day compliance function across a portfolio of domestic P&C, life and annuity, and international insurance companies. The ideal candidate is a hands-on compliance professional with deep regulatory knowledge, strong relationships with state insurance departments, and the ability to keep a complex, multi-jurisdictional insurance operation in good standing with its regulators. This position reports to the General Counsel and/or Chief Executive Officer.

Key Responsibilities

• Multi-Entity Regulatory Compliance
  • Manage ongoing regulatory compliance across all entities in the insurance group.
  • Monitor, interpret, and apply insurance laws and regulations across all relevant jurisdictions, including Arizona, Indiana, Oklahoma, and Puerto Rico.
  • Ensure all holding company structures, inter-company agreements, affiliated transactions, and enterprise arrangements comply with applicable insurance holding company acts and related statutes.
  • Support compliance oversight for the international insurer operating under the Puerto Rico International Insurance Center framework.
• Examination & Regulatory Relations
  • Lead preparation for and management of all state regulatory examinations, including financial and market conduct examinations.
  • Act as a primary point of contact with applicable insurance departments and regulatory bodies.
  • Maintain examination readiness programs; ensure all companies are in a continuous state of audit preparedness.
  • Respond to regulatory inquiries and work to resolve issues before escalation.
  • Prepare, review, and submit all required regulatory filings across all entities and jurisdictions on a timely basis.
• Transactions, Structures & Agreements
  • Review transactions, inter-company agreements, affiliated arrangements, and reinsurance contracts for regulatory compliance — the group operates primarily as a reinsurance business.
  • Support domicile selection, licensing, and regulatory structuring for the new life and annuity company formation.
  • Ensure all inter-company transactions and agreements are properly structured, documented, and filed in accordance with applicable law.
• Financial, Investment & Statutory Compliance
  • Monitor investment management and structuring across entities for compliance with applicable investment laws and statutory requirements.
  • Support statutory accounting compliance and the accuracy of regulatory financial reporting.
  • Review day-to-day transactions across the group for compliance with applicable laws, regulations, and company policies.
  • Escalate financial compliance issues to senior leadership and outside counsel as appropriate.
• Policies, Training & Compliance Program
  • Develop and maintain compliance policies, procedures, and internal controls across all entities.
  • Maintain a compliance calendar tracking all regulatory deadlines, renewal dates, and filing obligations.
  • Provide compliance guidance and training to management and staff.
  • Coordinate with outside regulatory counsel and compliance consultants as needed.

Qualifications

• Minimum 5-8 years of insurance regulatory compliance experience.
• Working knowledge of NAIC model laws, insurance holding company acts, and multi-state regulatory practices.
• Experience with state insurance department examinations, whether as a regulator, examiner, or company-side compliance professional.
• Ability to manage compliance obligations across multiple entities and jurisdictions simultaneously.
• Strong analytical and writing skills; ability to produce clear regulatory memoranda, compliance summaries, and management-level reports.
• Sound judgment and effective communication skills with regulators, management, and outside counsel.

Requirements

• Strongly Preferred
  • Juris Doctor (J.D.) degree from an accredited law school; active bar membership preferred but not required.
  • Prior experience working for or with a state insurance department or the NAIC.
  • Experience with both P&C and life/annuity compliance.
  • Experience supporting insurance company acquisitions or formations.
  • Familiarity with reinsurance structures and related regulatory considerations.

Personal Attributes

• Detail-oriented and proactive with a practical, solutions-focused approach.
• Comfortable managing multiple priorities across entities and jurisdictions in a fast-paced, entrepreneurial environment.
• High integrity and sound judgment; a reliable resource for senior leadership on compliance matters.
• Strong independent work ethic with excellent attention to detail.

Compensation & Benefits

• Offered salary commensurate with experience, plus discretionary bonus.
• $175 - $200k
• Lightstone offers our employees a comprehensive and competitive benefits program inclusive of:
  • Paid time off for vacation and sick leave.
  • Health, dental, and vision insurance, and wellness programs.
  • 401(k) and Roth retirement plans.
  • Flexible spending accounts (medical & dependent care).
  • Life and AD&D insurance with options for supplemental employee, spouse, and child.
  • Long-term and short-term disability insurance.
  • Commuter spending accounts (transit and parking).
  • Tuition assistance and employee assistance program.