Ledgebrook

Underwriter

• 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.
• Support E&S underwriting processes across various lines of business.
• Manage submission processes, ensuring everything is complete and clear for account clearance and set-up.
• Organize and maintain documentation necessary for underwriting operations.
• Contribute actively as a member of the underwriting support team in a remote setting.

Underwriting Assistant – West Coast

• 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!
• Get trained in the US insurance market, understand our products, and grow your technical and analytical skills

Junior Underwriting Support Analyst

Consultant

• lead functional configuration of Workday Financial modules
• gather and analyze business requirements from finance stakeholders
• design and implement end-to-end financial business processes
• support UAT, testing, and production deployment
• provide post-go-live support and system enhancements
• partner with finance teams for process improvements and optimization
• ensure compliance with financial policies and reporting standards

Workday Functional Consultant

Product Designer

• Design UI components, screens & flows in Figma
• Translate wireframes and specs into high-fidelity mockups
• Collaborate closely with frontend engineers during handoff
• Conduct usability reviews with stakeholders/subject matter experts and iterate on feedback
• Keep work organized, versioned, and documented in shared libraries
• Interview users to understand how the design of the application can better fit their needs

Junior UI/UX Designer

Vice President

• Develop analytical solutions and predictive pricing models
• Drive data strategy and ensure data integrity
• Communicate and collaborate across teams
• Own technical pricing models
• Mentor and grow team capabilities

AVP/VP, Specialty Pricing

• Lead, mentor, and develop a team of underwriters to achieve production and profitability goals
• Conduct regular file reviews, coaching sessions, and performance discussions
• Drive underwriting consistency, accountability, and execution across the team
• Manage and grow an individual book of business while maintaining profitability and underwriting discipline
• Maintain strong relationships with brokers and distribution partners to drive new business opportunities
• Monitor portfolio performance, rate adequacy, loss trends, and exposure management
• Collaborate with leadership on business planning, forecasting, and growth strategy

AVP, Underwriting Manager, SE

Support Engineer

• Provide superior support to the Underwriting and Operations Units.
• Work closely with Underwriting Assistants and Underwriters on Ledgebrook products.
• Understand multiple insurance products in the US market.
• Assist with eligibility determination and prioritization of opportunities.
• Organize and maintain file documentation and facilitate transactions with underwriting support resources.

Underwriting Support Analyst

Financial Planning and Analysis

• Own capital adequacy modeling across Ledgebrook’s risk-bearing entities, including captives and fronting/carrier structures, with a primary lens on AM Best’s BCAR framework
• Maintain and develop loss reserve models, including triangle-based methodologies and translate reserve adequacy findings into executive-level capital planning outputs
• Build and maintain dynamic capital planning models that stress-test surplus positions under adverse loss, premium growth, and reinsurance scenarios
• Lead underwriting profitability analysis by accident year, line of business, and entity—surfacing actionable insights on combined ratio drivers and reserve margin trends
• Support the annual planning and reforecasting cycle with entity-level P&L projections and capital deployment scenarios
• Serve as the internal subject matter expert on statutory capital requirements, risk-based capital (RBC) frameworks, and AM Best rating methodology as they relate to Ledgebrook’s balance sheet
• Collaborate cross-functionally with Actuarial, Accounting, and Underwriting to ensure reserve estimates, premium bookings, and capital positions are coherent and audit-ready
• Prepare materials for CFO and Board-level consumption: capital adequacy dashboards, reserve adequacy summaries, and scenario analyses tied to business plan milestones
• Support rating agency interactions and diligence processes, including BCAR sensitivity analysis and documentation
• Identify opportunities to automate and modernize capital and reserve reporting workflows

Senior FP&A Analyst

Strategy

• Coordinate with internal and external stakeholders to execute on key strategic initiatives
• Lead strategic efforts to launch new insurance products and data tools
• Build executive-level presentations that drive the story of Ledgebrook forward
• Partner with functional leaders across the organization to help shape the future of Ledgebrook’s data and technology advantage
• Identify and prioritize cross-functional opportunities
• Act as a lead project manager on key initiatives such as data migrations and enhancements, technology rollouts, and change management
• Engage with leadership to develop presentations outlining Ledgebrook’s strategic vision and business results
• Provide ad hoc support to key company events

Associate/Manager, Strategic Initiatives

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

Technical Project Manager

• Own the end-to-end delivery of complex technology initiatives and drive execution at scale
• Operate at the intersection of development, product, DevOps, IT, security, and compliance
• Lead multiple projects, manage dependencies, mitigate risks, and translate strategy into structured plans with clear milestones and success metrics
• Shape engineering excellence and optimize how teams build and release software in a high growth startup environment

Technical Project Manager – Infrastructure

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

Analyst, Strategic Initiatives

Security Engineer

• Design, implement, and manage secure AWS cloud architectures, including networking, IAM, and service configurations.
• Develop and enforce cloud security standards, policies, and guardrails across AWS environments.
• Implement automated security controls using tools like Terraform, AWS Config, Security Hub, GuardDuty, and Inspector.
• Collaborate with DevOps and engineering teams to integrate security into CI/CD pipelines (DevSecOps).
• Monitor and respond to security events using SIEM and cloud-native logging tools (CloudWatch, CloudTrail, AWS Security Hub, etc.).
• Conduct threat modeling, risk assessments, and security architecture reviews for AWS-based applications and services.
• Maintain and optimize identity and access management across AWS accounts using IAM, SSO, SCPs, and Organizations.
• Manage data protection strategies, including encryption (KMS), DLP, and secure key management.
• Support compliance initiatives (e.g., SOC 2, HIPAA, ISO 27001, or FedRAMP) with evidence collection and policy implementation.

Cloud Security Engineer – AWS Focus

Accountant

• Prepare accurate financial statements in accordance with US GAAP
• Manage month-end and year-end close processes, including journal entries, reconciliations, and variance analysis
• Leverage modern finance tools and AI-based solutions to improve efficiency, accuracy, and reporting insights
• Assist in process improvement and automation of accounting workflows
• Support audit processes and liaise with external auditors
• Assist with the design, implementation and maintenance of the company’s internal control environment.
• Partner with cross-functional teams (operations, product, tech & data) to support ad hoc projects and new business initiatives, as required in a scaling environment

GAAP Insurance Accountant

Accounting Manager

• Oversee the end-to-end process to prepare and review financial statements in accordance with U.S. GAAP.
• Mentor and supervise other accounting team members, including management of GAAP Accountant
• Own and manage month-end, quarter-end and year-end close processes for all entities to ensure timely and accurate reporting, including performing detailed balance sheet and income statement analysis, identifying and resolving variances.
• Leverage modern finance tools and AI-based solutions to improve efficiency, accuracy, and reporting insights
• Lead process improvement and automation of accounting workflows
• Coordinate and be the key point of contact with external auditors during the audit process.
• Assist with the design, implementation and maintenance of the company’s internal control environment.
• Partner with cross-functional teams (operations, product, tech & data) to support ad hoc projects and new business initiatives, as required in a scaling environment