Ledgebrook

Engineering Manager

• Own Finance Systems Architecture
• Lead the design and evolution of Ledgebrook’s finance systems centered around Workday Financials, ensuring they support scaling premium volume and product expansion.
• Build systems supporting: premium accounting claims accounting billing and cash application commissions reinsurance accounting financial reporting
• Design integrations between Workday and core insurance systems including: underwriting systems claims systems billing platforms reinsurance systems actuarial tools the data warehouse
• Define data mappings, reconciliation logic, validation rules, and error handling for finance workflows.
• Work with Finance, Accounting, and Actuarial teams to design scalable workflows for: premium accounting claims accounting billing and collections reinsurance settlements financial reporting
• Translate manual processes into system-driven, automated workflows.
• Build and maintain Workday reports and financial data flows used for: premium and claims reporting profitability analysis financial close processes
• Ensure outputs align with audit controls and regulatory requirements
• Own delivery of finance system changes including configuration, testing, UAT, and deployment.
• Lead and mentor a small team responsible for finance systems and integrations as the platform grows.

Engineering Manager – Finance, ERP Systems

Financial Planning and Analysis

• 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 – Finance Systems, ERP

Underwriter

• Ledgebrook is seeking experienced E&S Underwriting Assistant talent to join our growing team, whose mission is to build a profitable book of E&S business across expanding lines of business and coverages.
• 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.

Specialty Underwriting Assistant

• Curriculum Development for Ledgebrook University
• Collaborate within the Underwriting Excellence team to determine training, technology, and process improvement needs
• Assist with the creation of comprehensive training materials (presentations, manuals, video conferencing, and in-person sessions) for new and current underwriting staff
• Ensure adherence to internal underwriting guidelines and external regulatory requirements
• Update training materials regularly to reflect changes in appetite and internal software/systems
• Facilitates training on insurance appetite and company-specific systems
• Assist in providing feedback on, and refining the training process
• Help foster a culture of learning, quality, and accountability
• Assist in onboarding new hires, providing necessary training, and ensuring compliance with safety or industry regulations
• 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

QA Engineer

• Conduct regular audits of underwriting files across multiple lines of business to assess risk selection, underwriting rationale, and documentation quality.
• Identify inconsistencies, trends, and potential gaps in underwriting practices.
• Ensure adherence to internal underwriting guidelines and external regulatory requirements.
• Assist in providing feedback on and refining the QA/audit process: including file review workflows, audit schedules, scoring frameworks, and reporting templates.
• Partner with cross-functional stakeholders to align QA processes with evolving product and underwriting strategies.
• Build trust with underwriters and managers in order to deliver clear, constructive feedback, with a focus on continuous improvement and development of underwriting acumen.
• Collaborate with underwriting leaders to recommend training, documentation improvements, or process changes based on audit findings.
• Track and report on quality trends to various stakeholders with insight into root causes and proposed solutions.
• Maintain documentation of audit findings and action items.
• Collaborate within the Underwriting Excellence team to determine training needs, technology needs, and process improvement needs.

Underwriting Quality Assurance Specialist – Specialty

Paralegal

• Conduct legal research and analyze statutes, regulations, case law, and internal policy documentation.
• Prepare, review, and file legal documents including pleadings, affidavits, regulatory filings, and other supporting materials.
• Maintain organized legal files, contract repositories, and documentation databases to ensure audit-ready records.
• Support litigation and discovery efforts, including document collection, review, and fact investigation.
• Conduct initial information-gathering interviews and compile summaries for attorney review.
• Coordinate legal correspondence, manage calendars, and schedule meetings with internal and external stakeholders.
• Independently manage moderately complex to complex legal matters, escalating only highly sensitive issues as appropriate.
• Partner cross-functionally with Underwriting, Operations, and Finance to ensure legal alignment and documentation accuracy.
• Identify opportunities to improve legal workflows, documentation standards, and tracking processes.

Analyst

• Build executive-level presentations that drive the story of Ledgebrook forward
• Coordinate with internal and external stakeholders to execute on key strategic initiatives
• Conduct qualitative and quantitative research to build emerging business cases
• Partner with leadership to develop presentations and content that outline Ledgebrook’s strategic vision and business results to our Board of Directors, investors, and business partners
• Develop and exhibit a deep understanding of our enterprise-wide strategic initiatives and build business cases to influence the next stage of our journey
• Understand and compile data to frame Ledgebrook’s performance to key stakeholders
• Conduct market research to identify competitive intelligence, new product opportunities, and emerging trends in the E&S space
• Lead and project manage cross-functional efforts with our underwriting, tech, operations, and reinsurance teams on a variety of go-to-market initiatives
• Provide ad hoc support to key company events, such as partner summits and offsites