Jobs at Ledgebrook

Senior SDET responsible for architecting and maintaining Playwright-based automated test frameworks in TypeScript/JavaScript, integrating tests into CI/CD, implementing BDD with Gherkin, improving test stability via advanced locator strategies, testing RESTful APIs, performing targeted manual testing, and collaborating with engineering and product teams to raise overall quality.

Provide high‑level executive support to the CEO: manage complex calendar and travel, gatekeep communications, prepare meeting materials, coordinate board/investor logistics, run special projects, handle confidential information, and create systems to improve executive effectiveness and cross‑functional operations.

Provide analytical support to underwriting by reviewing inspection reports, monitoring policy-term risk developments, identifying quality gaps, and preparing structured insights for renewals and underwriting governance. Collaborate cross-functionally to improve risk transparency and underwriting consistency.

Conduct regular audits of underwriting files across General and Excess Liability to ensure compliance with internal guidelines and regulatory requirements. Identify trends and gaps, deliver constructive feedback and coaching to underwriters and managers, refine QA processes and scoring frameworks, and report quality trends with root-cause analysis and recommended improvements.

Lead and develop a team of underwriters while managing and growing an individual book of business. Drive underwriting discipline, profitability, broker relationships, and operational execution. Review and approve complex referrals, monitor portfolio performance, partner with actuarial/claims, support underwriting tools and guidelines, recruit and train talent, and contribute to strategic planning and compliance.

Own the finance systems product roadmap and deliver Workday ERP, billing, invoicing, and integrations. Design reinsurance back-office infrastructure, drive automation, lead agile delivery, coordinate QA/UAT, define KPIs, and ensure audit-ready financial workflows across Finance, Actuarial, Underwriting, and Engineering.

Lead capital adequacy and reserve modeling for risk-bearing entities, focusing on BCAR and loss reserving. Build dynamic capital planning and stress tests, provide underwriting profitability analysis, support forecasting/reforecasting, collaborate with Actuarial/Accounting/Underwriting, prepare CFO/Board materials, support rating agency diligence, and drive automation of capital and reserve reporting.

Lead development of predictive pricing models using machine learning and actuarial methods; define data needs, ensure data integrity, collaborate with underwriting/claims/finance, own technical pricing, and mentor actuaries and data scientists.

Support underwriters and operations by processing new business submissions, managing documents, and communicating with brokers and internal teams. Review submission data, help assess risk, learn insurance software systems, maintain organized records, and contribute to process improvements while receiving mentorship and on-the-job training.

Lead and manage cross-functional strategic initiatives for product and data, including data migrations, technology rollouts, governance, and change management. Partner with stakeholders to prioritize opportunities, build executive-level presentations and business cases, and support company events and leadership communications to drive enterprise strategy.

Provide operational support to underwriters and underwriting assistants across Ledgebrook products: manage submission intake, review for completeness, triage submissions against underwriting appetite and guidelines, obtain required broker information, maintain documentation, facilitate account setup and transactions, and support pre- and post-bind insurance activities.

Summer internship building and deploying AI-powered automations for FP&A and Accounting: audit workflows, prototype agentic LLM solutions, implement Python automation and orchestration, validate with finance teams, document builds, and present results to leadership.

Design UI components, screens, and flows in Figma; translate wireframes into high-fidelity mockups; collaborate with frontend engineers during handoff; run usability reviews and user interviews; maintain versioned design libraries and document components.

Lead functional configuration and design of Workday Financial modules, gather and analyze finance requirements, implement end-to-end financial processes, support UAT and production deployments, provide post-go-live support, and partner with finance teams for process improvements and compliance.

Lead and scale day-to-day IT support for a fully remote workforce. Supervise helpdesk staff, manage ticket queues and SLAs, act as Tier 2/3 escalation, administer Google Workspace and endpoints (Windows/macOS), support SaaS apps and MDM, improve workflows and documentation, and onboard/offboard employees.