Job Description

At Ledgebrook, we’re building a next-generation insurance infrastructure — fast, smart, and scalable — and are looking for a Chief Risk Officer to lead risk, actuarial, and reinsurance strategy for Stonehaven Specialty Insurance Company, Ledgebrook’s new third-party hybrid fronting carrier.

This role reports to the President and serves as one of Stonehaven’s independent control functions, with direct access to the Board of Directors. The Chief Risk Officer leads the enterprise risk, actuarial, reinsurance, and counterparty credit functions, and holds an equal seat with the Chief Program Officer and Chief Operating Officer in deciding which programs Stonehaven supports.

About the Role

Stonehaven is seeking a Chief Risk Officer to price risk, protect the balance sheet, and govern the counterparty credit exposure that comes with ceding the large majority of its premium. The successful candidate will be a seasoned risk executive with deep reinsurance, actuarial, and enterprise risk experience, a proven record of counterparty and collateral oversight, credibility with boards, regulators, and rating agencies, and the judgment to decline a program that does not clear Stonehaven’s appetite.

What You'll Do:

• Draft Stonehaven’s risk appetite statement covering program, counterparty, concentration, and retained underwriting risk, including the exception and breach-escalation processes.
• Build and own the enterprise risk management framework and ORSA, applying a three-lines-of-defense model, quarterly risk attestations from senior leaders, and stress testing for counterparty default, collateral failure, rating downgrades, and losses that exceed reinsurance caps.
• Lead the actuarial function: validate third-party bordereaux data, set expected loss ratios and development patterns before each program onboards, monitor actual-versus-expected results quarterly, and reserve gross, ceded, and net, with the net reserved independently.
• Ensure the retained share and any tail re-assumed above treaty caps are reserved and capitalized to full-carrier standards.
• Set reinsurance strategy, including preferred treaty wording on security, downgrade, offset, insolvency, and dispute resolution; risk-transfer testing to preserve statutory credit; and placements that keep net retention within appetite.
• Independently approve every reinsurer and collateral provider, including capacity that arrives attached to a program.
• Own the Third-Party Credit Risk Policy across reinsurers, MGAs, TPAs, captives, banks, and intermediaries, including credit standards, hard concentration limits, the counterparty risk register, and the Watch List.
• Require independent verification of all collateral, confirming letters of credit with issuing banks and trust assets with trustees, and maintaining collateral sufficiency with defined top-up triggers.
• Assess every proposed program for actuarial soundness, risk-appetite fit, and secured reinsurance capacity before it writes business, as a member of the Program Underwriting Committee.
• Lead the Risk & Capital and Reinsurance Security Committees, report risk, counterparty, and collateral status to the Board, and support the Reserve Committee and the independent actuary’s annual statement of opinion.
• Partner with Finance on the Schedule F, RBC, and AM Best BCAR impact of reinsurance and collateral decisions, and with Technology on the contract management system, collateral register, and concentration monitoring.
• Build and lead the risk organization, including actuarial, reinsurance and counterparty risk, portfolio and catastrophe risk, and risk data and reporting.

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

Must Haves:

• 15+ years in P&C actuarial, reinsurance, or enterprise risk, including senior leadership at a carrier, fronting carrier, or reinsurer.
• Associate of the Casualty Actuarial Society
• Direct experience structuring and negotiating reinsurance treaties, including capped quota shares, sliding-scale commissions, and collateralized capacity.
• Demonstrated counterparty credit and collateral risk management, including collateral verification, concentration limits, and watch-list governance.
• Ownership of an ERM framework and ORSA, with board-level risk reporting.

Nice to Haves:

• FCAS, CPCU, CERA, or FRM.
• Prior experience at a fronting, hybrid fronting, or program carrier.
• Experience with captive, ILS, or other collateralized reinsurance capacity.
• Experience working with rating agencies and regulators on capital and risk matters.

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 $250,000-550,000. 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.