Stonehaven - Director of Compliance

At Ledgebrook, we’re building a next-generation insurance infrastructure - fast, smart, and scalable - and are looking for a Director of Compliance who excels in providing practical compliance advice, services and oversight in a business-friendly manner to support the launch of Ledgebrook’s new third-party hybrid fronting carrier, Stonehaven Specialty Insurance Company.

This role will report to the Chief Operating Officer, with a dotted line to the Chief Risk Officer for risk oversight, and will work closely with the Stonehaven Programs team and collaborate when necessary and appropriate with Ledgebrook’s Legal, Regulatory and Compliance Department.

About the Role

Stonehaven is seeking a Director of Compliance to join our team. The successful candidate will be responsible for providing advice and services to Stonehaven on a wide range of matters and for the consolidation and reporting of compliance and regulatory requirements for the company. This role requires: strong analytical abilities, excellent communication skills; a business-focused approach; a comprehensive understanding of hybrid fronting carrier, Program Administrator/Managing General Agent and reinsurer relationships; experience providing advice related to state required insurance policy wordings; and familiarity with applicable insurance regulatory requirements, including state producer licensing laws.

What You'll Do:

• Provide direction and oversight regarding Stonehaven’s policy forms, notices, and related materials.
• Participate in the due diligence and vetting of Program Administrator/Managing General Agent opportunities, ensuring potential business partners have strong compliance protocols.
• Manage the repository of all third-party agreements, track the various compliance and regulatory requirements associated with those agreements and prepare monthly status reports of adequacy for distribution to all stakeholders and prepare quarterly for board presentation.
• Manage and assist with required insurance licensing matters for Stonehaven.
• Collaborate with Ledgebrook’s Legal, Regulatory and Compliance Department as necessary and appropriate on material or enterprise-related legal/regulatory/compliance matters.
• Work collaboratively across Stonehaven and the wider Ledgebrook organization to help ensure compliance risks are appropriately monitored, mitigated, and remediated where required.

About you

We love working with people who are eager to learn constantly and genuinely excited about the chaotic, rewarding process of building a company from the ground up.

You’ll be a great fit if you bring:

• A Strong Moral Compass: You believe in doing the right thing, period. We have a strict zero-tolerance policy for toxic behaviors.
• Customer-First Empathy: You are passionate about delivering an exceptional experience to everyone you work with, both inside and outside the company.
• Intellectual Curiosity: You naturally question the status quo and love finding innovative ways to solve problems.
• A Growth Mindset: You possess a hunger for continuous learning and want to constantly expand your skillset.
• Urgency & Prioritization: You can pivot quickly and balance the need to get things right with the speed of getting them done right now.
• A Solution-Oriented Outlook: When things go wrong, you don't look for blame—you immediately focus on how to fix it.
• Transparent Communication: You value honesty, clarity, and open feedback.
• Team-First Energy: You want to win together as a high-performing team and actively build connections across our remote locations.

Requirements

Need to Haves:

• Minimum of 7 years of experience in a compliance role, preferably for a (re)insurance company, insurance brokerage firm or program administrator/managing general agent
• Strong knowledge of U.S. insurance laws/regulations applicable to surplus lines insurers
• Experience with delegated authority underwriting, including fronting arrangements.
• Excellent written and verbal communication skills.
• Exceptional analytical and problem-solving abilities.
• Agility to manage multiple priorities and deadlines effectively.
• High degree of professionalism, ethics, and integrity.

Nice to Have:

• Relevant professional designations, such as CCEP.

Benefits

US Benefits 

• Full remote flexibility and asynchronous work culture.
• Unlimited PTO and fully paid sick leave.
• Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options.
• Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage.

Compensation

Compensation:

• The base salary range for this position is $150,000-250,000. This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including but not limited to experience, qualifications and geographic location.
• Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.

For Candidates Applying From The U.S.:

Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization. We are unable to offer sponsorship at this time.