Vice President, Insurance Compliance

Position Summary

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.

Key Responsibilities

• 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

• 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

• Review transactions, inter-company agreements, affiliated arrangements, and reinsurance contracts for regulatory compliance

• 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

• Maintain financial, investment, and statutory compliance across all entities

• 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

• 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

• Coverage of policies, training, and compliance program development

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

• 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

• 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

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