Compliance Director

Law and Compliance Chicago, Illinois


Position at Clear Spring Property and Casualty Company

Group1001 is a consumer-centric, technology-driven family of insurance companies on a mission to deliver outstanding value and operational performance by combining financial strength and stability with deep insurance expertise and a can-do culture. Group1001’s culture emphasizes the importance of collaboration, communication, core business focus, risk management, and striving for outcomes. This goal extends to how we hire and onboard our most valuable assets – our employees.

Clear Spring Property and Casualty Company

Company Overview

Clear Spring Property and Casualty is a leading provider of property and casualty insurance. Our future-forward strategy is rooted in deep industry knowledge and a mastery of emerging technologies. Clear Spring Property and Casualty Company is a subsidiary of Delaware Life Insurance Company and its parent company, Group1001. Our relationship with these organizations has yielded an innovative technology platform that provides smarter risk management solutions for property and casualty insurance brokers. Clear Spring is dedicated to Group1001's mission: making insurance more useful, intuitive and accessible for everyone. We’re confident in our forward-thinking products, and that you’ll love partnering with us.

Job Summary

The Legal and Compliance Department is currently seeking a Compliance Director for our Chicago, IL office.  The Compliance Director will be primarily responsible for implementing, maintaining and administering all aspects of the Company’s regulatory and compliance program for 50 states. Exercises judgment on moderately complex decisions falling within standard policies and regulatory requirements. As a small company, this role will work closely with senior management to accomplish the overall compliance function.  The Compliance Director will report to the Executive Vice President and General Counsel.

Main Accountabilities

  • Research and identify regulatory and compliance issues and work with senior management to design and implement changes to policies and procedures as appropriate
  • Serve as subject matter expert on forms, rules, filing procedures and regulatory compliance
  • Institute and manage a comprehensive compliance review program.
  • Assist with the design and delivery of compliance training to staff.
  • Manage relationships with state and federal regulators, coordinate information gathering with the Company’s business and functional units and follow up on issues or concerns raised through inquiries from regulators.
  • Continue developing overall knowledge of insurance regulatory compliance utilizing continuing education and professional certifications along with keeping abreast of current developments and trends
  • Represents the Company at trade associations meetings and conferences


  • Bachelor’s degree
  • Minimum 10+ years of relevant work experience, preferably in property & casualty insurance industry
  • In-depth knowledge and understanding of insurance laws, and regulations
  • Ability to provide management current information regarding standards of compliance with applicable rules/legislations
  • Effective communication skills, both verbal and written
  • Excellent analytical and problem-solving skills
  • Ability to analyze situations for compliance and business risk, and implement solutions to address and mitigate such risk
  • Commitment to customer service and quality