Ledgebrook

IT Support

• 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

IT/Helpdesk Supervisor

Underwriter

• Lead all underwriting operations and business performance for the Southwest Zone.
• Develop and execute regional business plans that deliver profitable premium growth while maintaining underwriting discipline.
• Own regional production, profitability, portfolio management, and service objectives.
• Monitor regional KPIs, submission flow, hit ratios, pricing adequacy, loss trends, and overall portfolio performance.
• Identify growth opportunities, market trends, and competitive dynamics to drive strategic decision making.
• Represent the Southwest Region with executive leadership and provide regular updates on performance, opportunities, and risks.
• Recruit, develop, mentor, and retain a high-performing underwriting team.
• Create a culture of accountability, collaboration, urgency, and underwriting excellence.
• Conduct regular coaching sessions, file reviews, performance evaluations, and career development discussions.
• Provide technical guidance and referral authority on complex, high-profile, or large casualty accounts.
• Ensure underwriting quality, pricing adequacy, and adherence to company underwriting guidelines.

Vice President, Southwest Zone Leader – Underwriting

• Lead all underwriting operations and business performance for the Northwest Zone.
• Develop and execute regional business plans that deliver profitable premium growth while maintaining underwriting discipline.
• Own regional production, profitability, portfolio management, and service objectives.
• Monitor regional KPIs, submission flow, hit ratios, pricing adequacy, loss trends, and overall portfolio performance.
• Identify growth opportunities, market trends, and competitive dynamics to drive strategic decision making.
• Represent the Northwest Region with executive leadership and provide regular updates on performance, opportunities, and risks.
• Recruit, develop, mentor, and retain a high-performing underwriting team.
• Create a culture of accountability, collaboration, urgency, and underwriting excellence.
• Conduct regular coaching sessions, file reviews, performance evaluations, and career development discussions.
• Establish clear underwriting expectations while reinforcing consistency, authority compliance, and execution.
• Provide technical guidance and referral authority on complex, high-profile, or large casualty accounts.
• Ensure underwriting quality, pricing adequacy, and adherence to company underwriting guidelines.
• Develop and strengthen executive-level relationships with key wholesale brokers and strategic distribution partners throughout the Northwest.

Vice President – Northwest Zone Leader, Underwriting

Data Analyst

• Lead analytical efforts to drive data informed decision-making across the entire organization by gathering, analyzing, and visualizing / presenting technical insurance data.
• Collaborate with data engineering, insurance product, claims, finance, and operations teams to improve data integrity and automate reporting capabilities using VBA, SQL, and Python.
• Transform complex insurance data into clear, compelling insights for both technical and non-technical stakeholders through required reporting and data visualization.
• Conduct deep-dive data analysis, develop analytical tools, deliver dedicated solutions to help other departments automate their workflows, and identify opportunities to enhance business performance and operational effectiveness.
• Provide ad hoc analytical support and research as needed to ensure Ledgebrook continues to operate with data-driven precision.

Data Associate – Data Excellence

Financial Planning and Analysis

• 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

Full Stack Engineer, Finance Engineering Team

Software Engineer

• Build and grow a high-performing engineering team across QA, support and engineering operations
• Manage the recruiting, onboarding/offboarding and ongoing team development while fostering technical excellence
• Mentor team members through technical challenges, support their continuous growth, and support their career growth
• Establish a culture of accountability, continuous improvement, customer focus, and operational excellence
• Own the product quality assurance strategy, tooling, frameworks, and quality standards
• Lead the QA organization responsible for test automation, release validation, regression testing, and quality governance
• Drive a shift-left quality culture across engineering teams
• Establish quality KPIs including defect escape rates, test coverage, release quality, and customer-reported issues
• Partner with engineering leadership to ensure quality is embedded throughout the SDLC
• Lead technical support and escalation management functions. Establish support processes, service levels, escalation paths, and operational reporting
• Drive root cause analysis and remediation efforts that improve platform stability and resilience
• Identify recurring customer issues and drive systemic improvements that reduce support burden
• Build data-driven operational reviews that help leadership make informed decisions
• Create transparency around engineering performance and improvement opportunities

Director of Engineering – Quality and Engineering Delivery

IT/Helpdesk Supervisor – Rippling Experience

Data Engineer

• 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.

Principal Data Engineer

• 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

Director – Data & AI Engineering

• 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.

Underwriting Training and Development Specialist – Specialty Lines

• 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

Senior Data Quality Analyst

Events

• 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.

Operations Coordinator, Events

General

• Build from Scratch: Take full ownership of originating, underwriting, and growing a brand-new Inland Marine book of business from $0 to a high-performing portfolio.
• Underwrite with Precision: Evaluate, price, and bind risks within your authority, focusing deeply on Builders Risk and Contractors Equipment, with the flexibility to intelligently underwrite up to 100% of property exposures when required.
• Cultivate Relationships: Actively market to and develop relationships with production sources; while an established book of wholesale broker connections is highly ideal, you will be expected to relentlessly hustle to establish new partnerships if needed.
• Operate Entrepreneurially: Act as the internal CEO of your book, collaborating with leadership to refine appetite, respond to market trends, and deploy our cutting-edge technology platform for maximum efficiency.

Inland Marine Underwriter

• 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

IT/Helpdesk Supervisor

Vice President, Southwest Zone Leader – Underwriting

Vice President – Northwest Zone Leader, Underwriting

Data Associate – Data Excellence

Full Stack Engineer, Finance Engineering Team

Director of Engineering – Quality and Engineering Delivery

IT/Helpdesk Supervisor – Rippling Experience

Principal Data Engineer

Full Stack Engineer, Finance Engineering Team

Director – Data & AI Engineering

Underwriting Training and Development Specialist – Specialty Lines

Senior Data Quality Analyst

Operations Coordinator, Events

Inland Marine Underwriter

Casualty Underwriter