Associate / Analyst, Strategic Initiatives

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.

Ledgebrook is seeking an experienced Associate or Analyst, Strategic Initiatives to join our Product & Data team. On this team, you will coordinate with internal and external stakeholders to execute on key strategic initiatives, lead strategic efforts to launch new data tools and insurance programs, and contribute analysis to executive-level presentations that drive the story of Ledgebrook forward.

In this role, you will partner with functional leaders across the organization (including engineering, IT, data excellence, finance, and pricing & analytics) to help shape the future of Ledgebrook’s data and technology advantage. You will be responsible for identifying and prioritizing cross-functional opportunities, and act as a lead project manager on key initiatives such as data migrations and enhancements, large scale technology roll outs and change management, data governance initiatives, etc. As part of these efforts, you will develop and exhibit a deep understanding of our enterprise-wide strategic initiatives and build business cases to influence the next stage of our journey.

• →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.

• 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.

• Familiarity with insurance data and key performance metrics
• Experience building out reporting views and dashboards
• Understanding of or interest in the data strategy of a rapidly scaling specialty insurance platform
• Technical savvy, including familiarity with PowerBI reporting and similar data visualization tools, a plus
• Strong written and verbal communication skills, with the ability to articulate key updates and influence stakeholders
• Strong project management and organizational skills, with the ability to move projects forward through ambiguity and on schedule
• Collaborative teammate, with ability to influence stakeholders across the organizations
• Experience preparing executive-level presentations using Microsoft PowerPoint and Excel
• Prior Property & Casualty insurance experience

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.