Ledgebrook

• Lead day-to-day IT helpdesk operations and supervise support team performance • Manage and prioritize ticket queues to ensure timely resolution and SLA adherence • Serve as the escalation point for complex technical issues (Tier 2/3 support) • Coach, mentor, and develop helpdesk team members • Support hiring, onboarding, and training of new IT staff • Provide IT support for a fully remote workforce, including onboarding and offboarding • Troubleshoot issues across devices, networks, and SaaS applications • Administer and support core systems, including Google Workspace and other SaaS tools • Manage endpoint environments across Windows and macOS, including MDM platforms • Improve helpdesk workflows, automation, and overall operational efficiency • Maintain clear documentation and contribute to a scalable knowledge base • Deliver a high-quality support experience through clear communication and user-focused service

Role Description We are seeking experienced Cyber, Tech and MPL underwriting talent to join our growing team whose mission is focused on building a profitable book of specialty lines business. Our 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 mould, we’re looking for you! As a member of the Specialty Lines team, you will regularly interact with our wholesale trading partners over the phone, virtually and in-person to drive submission flow and convert on the best opportunities quoted. We are looking for disciplined underwriting candidates that possess a strong overall cyber liability background with experience underwriting risks of all industries and sizes. Qualifications - A passion for delivering world-class customer service to our internal and external customers - Intellectual curiosity and a strong desire for innovation, rather than following the status quo - A hunger for continuous learning and opportunities to grow - Agile prioritization skills coupled with a keen sense of urgency - A strong drive and desire to win together as a high-performing team - A moral compass to "do the right thing, period." We have zero tolerance for toxic behaviors - An eagerness to actively participate and connect with the whole team, across remote locations - An honest, transparent communication style - A proactive, solution-oriented mindset Requirements - 2+ years experience as a cyber, tech and/or MPL underwriter - Experience working in the E&S market - Ability to work as a team player or independently in a fast-paced work environment - Deep wholesale broker trading relationships - Effective communication skills to articulate our appetite and develop wholesale broker relationships - Understanding of pricing and risk selection criteria to achieve underwriting profit - Advanced understanding of data analysis and execution of portfolio management objectives - Intellectual curiosity, problem solving skills, and a sense of urgency - Responsive, customer service focused mindset and behaviors - 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 to meet with assigned brokers or with the broader team to participate in industry conference or events 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 - A high degree of ownership, autonomy, and the opportunity to help build and shape a growing company - The chance to make a meaningful impact while working alongside an ambitious, high-performing team - Exposure to the challenges and opportunities of a fast-growing startup environment

Role Description We're looking for an exceptional claims leader to help build and scale a best-in-class claims organization. As Director, Claims, you'll partner closely with the AVP, Claims to lead our claims function, drive operational excellence, and ensure outstanding outcomes for our policyholders, trading partners, and business. This is a hands-on leadership role for someone who combines deep technical claims expertise with a passion for developing people, improving processes, and fostering a high-performance culture. You'll serve as a trusted advisor on complex claims, help shape claims strategy, oversee claim operations and vendor relationships, and play a critical role in recruiting, coaching, and developing the next generation of claims professionals. This role is ideal for a leader who is equally comfortable discussing coverage and liability strategy on a complex claim, analyzing claims performance trends, mentoring team members, and helping scale a modern claims organization. - Partner with the AVP, Claims to lead and scale a high-performing claims organization focused on delivering exceptional claim outcomes. - Serve as a senior technical resource and escalation point for complex, high-severity, litigated, and coverage-sensitive claims. - Provide guidance on coverage analysis, liability assessments, reserving, settlement strategy, and claim resolution. - Use data, analytics, and technology to monitor performance, identify trends, and continuously improve claims operations. - Oversee relationships with TPAs, defense counsel, and other external partners to ensure quality, consistency, and efficiency. - Recruit, coach, and develop high-performing claims professionals while fostering a culture of accountability, collaboration, and continuous improvement. - Partner cross-functionally with underwriting, actuarial, legal, finance, and operations teams to support profitable growth and informed decision-making. - Help shape claims strategy, governance, processes, and best practices as the organization continues to grow and evolve. Qualifications - Deep expertise in coverage analysis, liability evaluation, reserving, negotiation, and claim resolution. - Strong claims judgment and the ability to make sound, consistent decisions in complex situations. - Experience managing high-exposure, litigated, and coverage-sensitive claims. - The ability to balance customer outcomes, business objectives, and technical excellence. - Strong analytical and technological capabilities, including the ability to leverage data to improve claim outcomes, performance management, and operational effectiveness. Requirements - 10+ years of progressive claims experience within commercial insurance, specialty insurance, E&S, MGA, or carrier. - Significant experience handling complex casualty, liability, professional liability, financial lines, or specialty claims. - Demonstrated leadership experience managing and developing claims professionals. - Experience overseeing litigation, external counsel, TPAs, and vendor partners. - Strong understanding of claims operations, claims technology, analytics, and performance management. - Proven ability to influence stakeholders and drive organizational change. - Professional insurance designation (CPCU, AIC, ACII, or equivalent) preferred. Benefits

• Collaborate with product managers, designers, and other engineers to develop new features and enhance existing applications • Design and implement frontend and backend components using JavaScript (Node.js) and Python • Develop RESTful APIs and integrate with third-party services as needed • Write clean, maintainable, and efficient code following best practices and coding standards • Implement automated tests and ensure high code quality through code reviews and continuous integration • Optimize application performance and scalability to handle growing user demands • Dive into using and building LLMs (Large Language Models) to enhance our underwriters' productivity • Debug production issues using the latest tooling • Help set the direction of the small but growing engineering team

• Manage, mentor, and grow a 10-person data engineering team and a 3-person AI/ML team; own headcount planning and hiring across both • Set a unified roadmap where data infrastructure and AI/ML development reinforce each other • Build a culture of technical rigor, ownership, and delivery • Lead development of ML models using proprietary insurance data: risk scoring, pricing signals, anomaly detection, loss prediction • Own LLM integration strategy from prompt engineering and RAG pipelines to fine-tuning and agentic workflows • Drive AI automation across operations: underwriting intake, document processing, triage, internal tooling • Partner with the CTO on enterprise AI platform decisions: tooling, deployment infrastructure, model governance • Build the evaluation, monitoring, and feedback loops that turn experiments into production systems • Set architectural standards for pipelines, data modeling, and platform infrastructure • Own reliability, observability, and data quality across Snowflake, dbt, Airflow, and Terraform • Build semantic layers and data models that serve underwriting, pricing, finance, and executive reporting • Establish data governance, quality frameworks, and documentation standards that scale • Collaborate with actuaries, underwriters, engineers, and product leaders to translate business needs into AI and data solutions • Operate as a senior technical voice in planning, roadmap, and strategy discussions

• Architect the Data Platform – Own the end-to-end design of our data infrastructure. • Make the foundational calls on pipeline architecture, data modeling patterns, and platform evolution across Snowflake, dbt, Airflow, and Terraform. • Define Engineering Standards – Establish and enforce practices around data quality, testing, observability, and deployment that the rest of the team builds on. • Enable Data-Driven Decisions at Scale – Design semantic layers and data models complex enough to support underwriting, finance, and executive strategy. • Drive Data Governance – Own the governance posture: data contracts, SLAs, lineage, and documentation. • Shape the ML and AI Foundation – Partner with data science and engineering leadership to ensure the platform supports advanced analytics, ML pipelines, and AI initiatives. • Elevate the Team – Mentor engineers, conduct rigorous code and design reviews, and actively close skill gaps. • Partner at the Leadership Level – Engage directly with actuarial, underwriting, finance, and product leaders to translate business complexity into technical roadmap.

• Curriculum Development for Ledgebrook University Create comprehensive training materials (presentations, manuals, video conferencing, and in-person sessions) for new and current underwriting staff to improve underwriting skills, system proficiency and compliance knowledge. • Expand and grow content for e-learning, virtual instructor-led training, and in-person workshops. • Update training materials regularly to reflect changes in appetite and internal software/systems. • Collaborate within the Underwriting Excellence team to determine training, technology, and process improvement needs. • Ensure adherence to internal underwriting guidelines and external regulatory requirements. • Coordinate and schedule virtual onboarding and training sessions for new hire UWs with LBU Officer, subject matter experts and other identified stakeholders. • Manages all aspects of in-person workshops (Road Shows), including but not limited to site selection, budget oversight, and execution of on-site logistics. • Promotion of upcoming training opportunities and workshops to employees to ensure high participation. • Facilitates training on insurance appetite and company-specific systems. • Assist in onboarding new hires, providing necessary training, and ensuring compliance. • Maintaining, tracking, and updating employee training records. • Collaborate within the UW Excellence Team to identify skill gaps, performance issues, and training needs within the Underwriting team. • Regularly seeking and acting on feedback from trainees and stakeholders.

• Lead analytical efforts to analyze complex data to ensure its integrity and accuracy • Play a key role in driving organizational trust in reporting and analytics • Ensure adherence to regulatory requirements • Collaborate with engineering, data excellence, pricing and analytics, finance, and compliance teams to improve data quality • Proactively query databases, review data and dashboards, understand data flow processes, and support implementation of data initiatives

• Support the Operations team with calendar management, helping balance meetings, strategic work, and other priorities while ensuring schedules remain organized and efficient. • Help coordinate onboarding schedules, prepare welcome packages, and partner with team leaders to ensure new hires have a seamless start from day one. • Coordinate laptop orders, equipment provisioning, shipments, returns, and related logistics to ensure employees have the tools they need to succeed. • Prepare meeting notes and action items from Operations team meetings and leadership sessions, ensuring key decisions and follow-ups are documented and tracked. • Manage co-working space reservations, coordinate office-related needs, manage incoming mail and support day-to-day operational administration. • Organize team events, offsites, team dinners, and other employee engagement activities, including restaurant reservations and entertainment arrangements. • Assist with travel bookings, itineraries, and agendas for business trips and team gatherings. • Anticipate needs, solve problems proactively, and continuously look for ways to improve administrative processes and team efficiency.

• Join our growing team focused on building a profitable book of casualty business • Deliver market relevant solutions to our wholesale trading partners • Interact with wholesale trading partners to drive submission flow • Convert on the best opportunities quoted