Senior Accounting Manager - Insurance

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 forward-thinking and highly motivated Insurance Senior Accounting Manager – Insurance who will report directly into the Group Controller.

As Ledgebrook continues to scale, our Finance function is also scaling - we are building a team of professionals that have deep insurance and finance expertise, are passionate about leveraging AI and high-tech systems, and are excited to support a company that is building from the ground up.

In this role, we are seeking a Senior Accounting Manager - Insurance who is excited not only about accounting excellence, but also about how technology can transform finance operations. You will be responsible for overseeing insurance accounting and reporting, working within the Finance Team and other functional teams. We want someone who doesn't just execute the process but actively looks to improve it — ideally with hands-on experience using AI tools or building automation to streamline insurance accounting workflows.

What You’ll Do:

• Own monthly, quarterly and annual financial close processes for all assigned insurance entities, ensuring timely and accurate reporting.
• Ensure timely and accurate recording of journal entries, accruals, estimates and adjustments related to premiums, commissions, claims, deferred acquisition costs and other expenses.
• Oversee balance sheet reconciliations, income statement fluctuation analysis and supporting schedules to ensure completeness and accuracy of financials in compliance with applicable accounting standards (US GAAP, NAIC Statutory Accounting Principles and state regulatory requirements.
• Develop, implement and maintain accounting policies, procedures and documentation to support financial reporting and strengthen internal controls.
• Lead accounting process improvement initiatives to enhance efficiency, scalability and accuracy.
• Collaborate with FP&A on financial forecasts, budget vs. actual variances and management 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

• Bachelor’s degree in accounting, finance or a related field required.
• Minimum of 5-7 years of progressive accounting experience, preferably within the insurance industry with an understanding of property and casualty insurance accounting and statutory reporting.
• Experience preparing and reviewing financial statements.  
• Familiarity with accounting and reportingee software and proficient in Microsoft Excel. Workday and Gain experience is a plus.
• Experience of using AI tools to improve or automate financial processes.
• Excellent analytical, problem solving and organizational skills, with strong attention to detail.
• Ability to multi-task, prioritize, and work independently in a collaborative and fast-paced setting.

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 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

• The base salary range for this position is [$160,000 - $180,000 USD] 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.