Property Underwriter

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 experienced Property Underwriters to join our growing team whose mission is focused on building a profitable book of property business. Ledgebrook’s vision is to deliver market relevant solutions to our key wholesale trading partners in a more frictionless environment that places an emphasis on efficiencies and quality to meet or exceed our broker’s overall needs in a risk differentiated manner. If you possess an entrepreneurial passion that includes a proven track history of delivering underwriting excellence and are seeking an opportunity to break out of the traditional insurance company mold, we’re looking for you! 

As a member of the Ledgebrook Property team, you will regularly interact with our wholesale trading partners over the phone, virtually, and in-person to drive in-appetite submission flow and convert on the best opportunities quoted. We are looking for disciplined underwriting candidates that possess a strong overall E&S property background with experience across multiple industry segments, i.e. manufacturing, distributors, real estate, retail, mercantile, habitational, and hospitality. 

We are flexible with both a candidate’s experience level and physical work location. The actual position title (Underwriter, Senior UW, Executive UW, etc.) and role (Individual Contributor, Team Lead, etc.) will be dependent on a candidate’s specific experience and qualifications. We currently operate in a fully remote work environment, so we’re more focused on your experience and cultural fit than where you physically sit!

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.

● 5+ years experience as a Property underwriter 

● Experience working with non-admitted paper in the E&S marketplace 

● Ability to work as a team player or independently in a fast-paced work environment ● Ability to underwrite new business and renewal policies for Property 

● Deep wholesale broker trading relationships 

● Effective communication skills to articulate the Ledgebrook appetite and value proposition to develop and advance wholesale broker relationships 

● Understanding of pricing and risk selection criteria to achieve profitable loss ratios ● Advanced understanding of data analysis and execution of portfolio management objectives ● Innovative problem solving and solutioning skills 

● Responsive, customer service focused mindset and behaviors

● Intellectual curiosity and comfort in dealing with the concept of a blank sheet of paper ● Ability to make timely decisions with appropriate information and consultation ● A strong entrepreneurial drive and desire to build and win together as a high performing team 

● Ability to travel independently to meet with assigned brokers or with the broader Ledgebrook team to participate in industry conference or events