Careers > OPEN POSITION

Head of Insurance Compliance

Remote - US

Are you tired of the inefficiencies and frustrations of legacy systems, outdated processes and corporate red tape? At Ledgebrook we believe your career in insurance compliance can be so much more. You bring the expertise and drive; we’ll provide the platform to help you thrive and shape the future of the insurance industry. 

Ledgebrook is a tech-enabled E&S MGA on a mission to modernize Specialty insurance. The industry is burdened with legacy technology and inefficient processes, preventing innovation at scale. We are changing that. Our goal is to become the best-in-class full-stack insurance and re/insurer, leveraging AI and data-driven insights to revolutionize underwriting, pricing, and risk selection. To help us get there, we are seeking a Head of Insurance Compliance to join our team.

About the Role

This key role will support Ledgebrook’s growth by establishing a robust compliance framework, ensuring we operate within the insurance regulatory landscape. The ideal candidate is a hands-on leader with deep knowledge of insurance regulatory requirements. Reporting to the COO, the successful candidate will collaborate closely with leadership and external partners, helping to scale the business while mitigating compliance risks.

What You’ll Do: 

  • Compliance Strategy: Oversee all regulatory compliance efforts across the company, ensuring adherence to state and federal insurance regulations, as well as other relevant laws and industry standards.
  • Risk Management: Develop and implement risk management strategies, identifying areas of potential risk, advising leadership on risk mitigation, and helping the company navigate insurance regulatory challenges.
  • Risk Assessments: Conduct audits and risk assessments to identify insurance compliance gaps.
  • Regulatory Liaison: Serve as the primary point of contact for regulatory agencies, ensuring effective communication and resolution of regulatory issues in a timely manner.
  • Insurance Compliance Program Development: Establish and monitor an effective insurance compliance program, ensuring Ledgebrook’s continued adherence to the legal requirements of the insurance industry, especially in E&S (Excess & Surplus) and Specialty markets.
  • Insurance Products: Review and assess insurance products, policies, and company practices for regulatory compliance.
  • Futureproof: Stay updated on emerging regulatory trends and industry changes.

About You

About You

At Ledgebrook, we are passionate about creating a team that is on a continuous learning journey and that shares our excitement about building a company from the ground up. Some of the characteristics we hold dear are:

  • A Commitment to Compliance & Integrity: You are driven by a deep understanding of the importance of legal and regulatory compliance in a rapidly evolving industry.
  • Innovative Thinking: You thrive on finding creative solutions to complex legal and regulatory issues, especially in the face of disruption.
  • Collaboration & Communication: You are an effective communicator who excels at collaborating with leadership, product teams, and external stakeholders.
  • Adaptability & Growth: You possess a growth mindset and are excited by the prospect of scaling a business and its compliance operations in an emerging market.
  • Attention to Detail: You are meticulous in managing compliance programs, ensuring everything is in order while managing risks effectively.

Must Haves

  • Experience: 8+ years of experience in regulatory compliance within the insurance or InsurTech industry.
  • Insurance Knowledge: Deep understanding of insurance laws, particularly in relation to E&S, Specialty lines, insurance filings and other complex products.
  • Regulatory Expertise: Extensive knowledge of the regulatory environment for the insurance industry, including state insurance departments, the NAIC (National Association of Insurance Commissioners), and other relevant regulatory bodies.
  • Risk Management: Proven ability to assess, manage, and mitigate risk at an organizational level.
  • Communication Skills: Exceptional verbal and written communication skills, with the ability to distil complex concepts for non-regulatory teams and stakeholders.
  • Problem Solver: Ability to think critically and make decisions that balance risk with business objectives.

Nice to Haves

  • Startup Experience: Experience working in a high-growth startup environment.
  • Technology Savvy: Familiarity with emerging technologies within the insurance industry, specifically around regulatory compliance software or tools.
  • Global Knowledge: Experience navigating international regulatory frameworks.

At Ledgebrook, we’re building something truly special. If you’re excited by the opportunity to shape the future of insurance, thrive in a fast-paced, high-growth environment, and are passionate about compliance and legal innovation, we’d love to hear from you. Join us in our mission to bring Specialty insurance into the modern era and become part of a team where Care, Strive, and Thrive Together are more than just words—they’re how we work.

About Ledgebrook

Our next-gen tech stack supports faster, risk differentiated solutions to be crafted and delivered in response to the fast-paced needs of the E&S market. Our data driven approach seeks to unlock more opportunities and value from every submission received, leading to a faster ‘yes’ more frequently, but may also lead to a quick ‘no’.

We are motivated and structured to move faster than traditional insurance organizations. To fully align business objectives with a long-term view that supports our culture and values, all employees will have the opportunity to participate in company ownership through equity grants. We aim to deliver a highly compelling overall employee value proposition and a total compensation package that couples equity grants with base pay and benefits offerings.

At Ledgebrook, as a unified team of company stewards, we will Care, Strive and Thrive together!

What Ledgebrook can offer you

Competitive salary

and meaningful equity ownership

Health Insurance

100% employer-paid option available

Additional benefits

available include 401k plan,  dental, vision & other options

Remote work,

flexible hours

Unlimited

time off policy

Ownership,

autonomy, purpose

What Ledgebrook can offer you

Competitive salary

and meaningful equity ownership

Ownership,

autonomy, purpose

Remote work,

flexible hours

Unlimited

time off policy

Ledgebrook is proud to be part of

How to Apply

Apply Now

Ready to Learn More?

Contact Us