Ledgebrook

Underwriter

• Ledgebrook is seeking experienced E&S Underwriting Assistant talent to join our growing team.
• You will regularly interact with Ledgebrook’s underwriters and wholesale trading partners over the phone, virtually, or in-person to facilitate various transactions independently or with limited guidance.
• We are looking for candidates with a strong overall E&S support background across various lines of business, including a curiosity to gain a deeper knowledge of our business.

Underwriting Assistant

• Support underwriters and operations staff by helping process new business submissions and manage documents
• Communicate with insurance brokers and internal teams to collect key information
• Assist in reviewing submission data and helping assess risk
• Learn how to navigate insurance software systems and maintain organized records
• Contribute to continuous improvement - your ideas matter here!

Underwriting Operations Associate

Compliance

• Conduct regular and ad-hoc audits of policies, endorsements, renewals, and other operational workflows.
• Review files to confirm all required steps, documents, and communications were completed per internal SOPs and underwriting guidelines.
• Identify missing documentation, process deviations, and compliance risks; flag findings with clear, actionable feedback.
• Perform root-cause analyses on recurring issues and collaborate with process owners to design corrective measures.
• Prepare structured QA reports summarizing audit results, trends, and improvement opportunities.
• Monitor and verify the implementation of corrective actions to ensure audit findings are properly resolved and sustained over time.
• Support creation and maintenance of QA dashboards, checklists, and audit trackers.
• Recommend updates to operational procedures, training materials, or automation rules based on audit insights.
• Work closely with Underwriting, Ops, Compliance, and Product teams to clarify audit expectations and raise process awareness.
• Participate in workflow reviews and testing of new tools, ensuring they align with compliance and quality standards.
• Provide mentorship and feedback to Operations team members on audit findings and best practices.

Quality & Compliance Specialist

Recruitment

• Lead the execution of recruitment strategies, ensuring they align with the company's mission, goals, and culture.
• Partner with our external recruitment agency while also proactively sourcing directly to build and nurture a strong, diverse pipeline of high-caliber candidates for current and future hiring needs.
• Manage the recruitment process, from job posting to interviewing, to offer acceptance, ensuring a seamless, candidate-friendly experience while balancing speed and quality.
• Partner closely with hiring managers and external recruitment consultants to understand role requirements, provide strategic insights, and deliver top talent for critical positions.
• Champion Ledgebrook’s employer brand by ensuring candidates understand our unique mission and the opportunity to be a part of the future of insurance.
• Utilize analytics and data to assess, report and improve the effectiveness of recruitment strategies, continually optimizing for better results.
• Identify opportunities to streamline recruitment processes, driving efficiency and improving overall candidate experience.
• Help create a diverse and inclusive work environment by ensuring inclusive hiring practices and engaging diverse talent pools.

Talent Acquisition Partner

Product Manager

• Own the product lifecycle for Ledgebrook’s data platform and infrastructure initiatives from discovery through delivery and measurement.
• Lead agile ceremonies (sprint planning, retrospectives, standups) and manage Jira: creating, refining, and validating stories to ensure clarity and readiness for release.
• Partner with engineering leads to translate complex technical initiatives into clear deliverables, balancing strategic priorities with day-to-day execution.
• Collaborate with stakeholders across engineering, actuarial, underwriting, finance, and operations to understand needs and define roadmap priorities.
• Define success metrics and use data to track outcomes, improve processes, and guide investment decisions.
• Ensure technical readiness for releases, coordinating QA, documentation, and stakeholder communication.
• Lead roadmap planning, aligning quarterly and annual objectives with company OKRs and evolving business needs.
• Champion internal adoption of data and infrastructure tools, ensuring teams across the company derive measurable value.
• Drive continuous improvement in team velocity, delivery predictability, and agile maturity.

Product Manager – Data and Infrastructure

Machine Learning Engineer

• Develop ML-driven pricing models to generate underwriting decisions autonomously, increasing capacity from 100 to 1000+ submissions per underwriter per month.
• Design models to forecast risk and optimize pricing strategies using structured and unstructured data.
• Implement AI models that extract insights from loss run reports, reducing manual work and accelerating turnaround times.
• Use NLP and deep learning to process structured and unstructured insurance documents, improving decision-making efficiency.
• Develop and deploy computer vision models to analyze property imagery for key underwriting features such as roof material, condition, and structure.
• Build a chatbot leveraging LLMs to assist underwriters with document analysis and risk assessment.

AI/ML Engineer

• Lead the development and execution of recruitment strategies, ensuring they align with the company's mission, goals, and culture.
• Partner with our external recruitment agency while also proactively sourcing directly to build and nurture a strong, diverse pipeline of high-caliber candidates for current and future hiring needs.
• Manage the recruitment process, from job posting to interviewing, to offer acceptance, ensuring a seamless, candidate-friendly experience while balancing speed and quality.
• Partner closely with hiring managers and external recruitment consultants to understand role requirements, provide strategic insights, and deliver top talent for critical positions.
• Champion Ledgebrook’s employer brand by ensuring candidates understand our unique mission and the opportunity to be a part of the future of insurance.
• Utilize analytics and data to assess, report and improve the effectiveness of recruitment strategies, continually optimizing for better results.
• Identify opportunities to streamline recruitment processes, driving efficiency and improving overall candidate experience.
• Help create a diverse and inclusive work environment by ensuring inclusive hiring practices and engaging diverse talent pools.

Lead Talent Acquisition Partner

Engineering Manager

• Lead and mentor a team of full stack engineers, fostering technical excellence, collaboration, and accountability.
• Drive agile execution - help run standups, sprint planning, retros, and ensure consistent delivery against roadmap commitments.
• Partner with product managers and stakeholders to clarify requirements, define milestones, and deliver business outcomes.
• Stay hands-on technically: conduct code reviews, guide architecture decisions, and unblock complex technical challenges.
• Own the delivery pipeline - ensure code quality, testing, CI/CD automation, and operational readiness.
• Shape our system architecture across Node.js, Typescript, Python, and AWS services to support performance, scalability, and maintainability.
• Foster engineering culture that values craftsmanship, transparency, and continuous improvement.
• Collaborate with AI/ML engineers to integrate models and automation into internal products and workflows.
• Champion DevOps and reliability best practices, ensuring uptime and performance of critical systems.
• Scale process and people - recruit, onboard, and grow a high-performing engineering team.

Analytics Engineer

• Partner with leadership, engineers, underwriters, and actuaries to understand data requirements.
• Design, develop and deploy a scalable modern data stack to support business objectives (application, reporting and the like).
• Design data conceptual and logical models to support business workflow, application functionality and reporting requirements.
• Design data architecture to accommodate data pipelines to move data across a multitude of platforms.
• Craft a data governance structure to ensure integrity of data and information flow has proper cadence and structure to exceed business objectives while ensuring scalability to support growth initiatives.
• Define security and backup procedures.
• Communicate effectively with technical and non-technical audiences.
• Build a data-driven culture throughout the organization.
• Elevate our technology and best practices through partnership with the Director of Data and Analytics Engineering.

Data and Analytics Engineer

Business Analyst

• Lead analytical efforts to drive data informed decision-making across the entire organization
• Gather, analyze, and visualize/present technical insurance data
• Collaborate with data engineering, insurance product, claims, and finance teams to improve data integrity and automate reporting capabilities
• Transform complex insurance data into clear, compelling insights for both technical and non-technical stakeholders
• Conduct deep-dive data analysis, develop analytical tools, and identify opportunities to enhance business performance and operational effectiveness
• Provide ad hoc analytical support and research as needed