Stonehaven - Director of Underwriting

At Ledgebrook, we’re building a next-generation insurance infrastructure - fast, smart, and scalable - and are looking for a Director of Underwriting to join Stonehaven Specialty Insurance Company, Ledgebrook’s new third-party hybrid fronting carrier.

This role reports to the Chief Programs Officer (CPO) and owns underwriting quality and discipline across the full program book, setting and enforcing underwriting appetite and guidelines, and supervising the Underwriting Manager(s) who handle day-to-day program-level underwriting oversight.

About the Role

Stonehaven is seeking a Director of Underwriting to set and enforce underwriting appetite and guidelines across all programs, supervise the Underwriting Manager(s) who handle day-to-day program-level oversight, and serve as the senior underwriting authority in new-program due diligence and BAA negotiations. The successful candidate will bring deep delegated-authority/MGA-oversight underwriting experience and a track record setting guidelines and appetite for a book of business, not just executing within them.

What You'll Do:

• Set and maintain enterprise underwriting appetite, standards, and guidelines across all programs, in coordination with the CPO and CRO’s Actuarial function.
• Supervise and develop the Underwriting Manager(s); review their program-level underwriting audits and sign off on findings that need escalation.
• Own the underwriting side of new-program due diligence (“underwrite the underwriter”) jointly with Business Development, escalating go/no-go recommendations to the CPO.
• Serve as the senior underwriting authority in BAA negotiations — binding authority limits, referral thresholds, and underwriting guideline provisions — working with Legal on final language.
• Track underwriting audit findings to remediation across the book and report portfolio-level underwriting quality trends to the CPO.
• Coordinate with Actuarial and Claims on loss experience, emerging trends, and guideline changes across programs.

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:

• 10+ years of P&C underwriting experience, including 4+ years managing or supervising underwriters in a delegated-authority/MGA-oversight environment.
• Track record setting underwriting guidelines and appetite for a book of business, not just executing within them.
• Experience negotiating binding authority agreement underwriting terms directly with program partners.

Nice to Haves:

• CPCU, AU, or equivalent underwriting designation.
• Prior fronting-carrier, program administrator, or MGA-side underwriting leadership experience.
• Experience across multiple lines of business relevant to Stonehaven’s target programs.

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 $250,000-350,000. 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.

Ledgebrook may use Artificial Intelligence (“AI”) as part of the job application process, including to assist us in evaluating your application. AI is used as a support tool, and hiring decisions are made by human recruiters. By submitting your information, you acknowledge that the company may use AI tools as part of our evaluation. If you need a reasonable accommodation or alternative review process because of a disability or other legally protected basis, contact hiring@ledgebrook.com. Requesting an accommodation will not negatively affect your application.