Head of Capital Modeling

Ledgebrook is an AI-native specialty insurance platform. When a business needs coverage that is custom and complex, its broker comes to us, and our underwriters give them an answer, often in hours rather than weeks.

We built our technology from scratch, with AI in it from the first line of code. The technology helps price the risk; the underwriter uses their judgment to decide. There are always two hands on the wheel.

We are insurance industry insiders, and we eat our own cooking: Ledgebrook writes the policy and shares the risk through our own carrier, Ledgebrook Specialty, rated A- (Excellent) by AM Best. We work exclusively through wholesale brokers.

Our vision: to make the wheels of insurance spin faster.

At Ledgebrook, everything we do is driven by our culture: Care, Strive, Thrive Together. To succeed in modernizing the industry, we must first succeed in changing the way we do business. Talent density is our north star—fewer, better people working together as one. To that end we’ve replaced all individual incentives with generous equity packages—we play as a team, we win as a team. Everyone benefits handsomely from Ledgebrook’s success.

About the Role

We are seeking a highly analytical and insurance-fluent Head of Capital Modeling to own capital management and financial planning across Ledgebrook’s risk-bearing entities. This is a high-visibility, high-impact role sitting at the intersection of FP&A, actuarial finance, and enterprise risk.

As Ledgebrook scales its risk-bearing footprint, we need someone who can independently drive capital adequacy analysis, model loss reserve scenarios, and translate complex outputs into clear, decision-ready insights for senior leadership. This is not a generalist FP&A seat and prior experience in insurance capital modeling, statutory finance, or a closely adjacent function (e.g., ERM, reinsurance analytics, rating agency analysis) is required.

We see a natural path for this individual to take on expanded scope, including direct partnership with the CFO on rating agency relationships, reinsurance capital optimization, and enterprise risk reporting, as Ledgebrook’s carrier operations mature.

Key Responsibilities

• Own capital adequacy modeling across Ledgebrook’s risk-bearing entities, including captives and fronting/carrier structures, with a primary lens on AM Best’s BCAR framework
• Maintain and develop loss reserve models, including triangle-based methodologies and translate reserve adequacy findings into executive-level capital planning outputs
• Build and maintain dynamic capital planning models that stress-test surplus positions under adverse loss, premium growth, and reinsurance scenarios
• Lead underwriting profitability analysis by accident year, line of business, and entity—surfacing actionable insights on combined ratio drivers and reserve margin trends
• Support the annual planning and reforecasting cycle with entity-level P&L projections and capital deployment scenarios
• Serve as the internal subject matter expert on statutory capital requirements, risk-based capital (RBC) frameworks, and AM Best rating methodology as they relate to Ledgebrook’s balance sheet
• Collaborate cross-functionally with Actuarial, Accounting, and Underwriting to ensure reserve estimates, premium bookings, and capital positions are coherent and audit-ready
• Prepare materials for CFO and Board-level consumption: capital adequacy dashboards, reserve adequacy summaries, and scenario analyses tied to business plan milestones
• Support rating agency interactions and diligence processes, including BCAR sensitivity analysis and documentation
• Identify opportunities to automate and modernize capital and reserve reporting workflows

About you

We’re looking for people to join us with:

• Deep familiarity with insurance capital frameworks: you’ve worked inside a carrier, captive, reinsurer, or rating agency context and understand how capital adequacy is built, defended, and managed
• Intellectual horsepower and genuine curiosity: you don’t just run the model, you interrogate the assumptions
• Demonstrated fluency in AI: you actively explore and apply generative AI tools in your day-to-day workflow (e.g. Claude, Copilot, python-based assistants) to enhance financial analysis, scenario modeling, and management reporting
• Workflow automation mindset: you identify opportunities to streamline and improve FP&A processes using AI and automation (e.g. forecast updates, variance analysis, data reconciliation), improving speed, accuracy, and scalability
• A bias toward clarity: you can translate actuarial and statutory complexity into plain language for CFOs, board members, and investors
• Agile prioritization: you balance rigor with velocity and know when “directionally right today” beats “perfect next quarter”
• A collaborative, no-ego working style: this team wins together and communicates transparently across remote locations
• Proactive ownership: you surface problems early and come with solutions, not just observations

Requirements

• Bachelor’s degree in Finance, Actuarial Science, Mathematics, Accounting, or a related field 
• 5–7 years of directly relevant experience in insurance capital management, ERM, actuarial finance, or statutory FP&A at a carrier, captive, reinsurer, MGA with risk-bearing exposure, or rating agency
• Demonstrated hands-on experience with AM Best’s BCAR model, meaning you have built, maintained, or stress-tested BCAR analyses for P&C entities
• Working knowledge of loss reserving methodologies
• Familiarity with statutory financial statements and their relationship to capital adequacy
• Advanced financial modeling skills and expert-level Excel proficiency
• Experience with Workday and Snowflake a plus
• Strong verbal and written communication skills with experience presenting to CFO and C-suite audiences
• Ability to operate independently in a remote, fast-moving environment with evolving priorities

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.

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.

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 or Canada 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.

Compensation

Compensation:

• Base Salary Range $150,000-$175,000. 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 experience, qualifications, geographic location and other relevant factors. 
• Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.