Ledgebrook

• 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

• Manage a highly dynamic and complex calendar for the CEO, including scheduling internal and external meetings, prioritizing competing demands, and ensuring time is aligned with company priorities. • Own all travel arrangements, including flights, accommodations, itineraries, and logistics for business travel, offsites, conferences, and leadership meetings. • Manage inbound requests, communications, and meeting requests with strong judgment and prioritization. • Prepare meeting agendas, briefing materials, notes, and follow-up action items. • Assist with board meeting logistics, investor coordination, leadership offsites, and executive communications. • Own or support high-priority cross-functional initiatives on behalf of the CEO, ranging from operational improvements to internal events, culture initiatives, and ad hoc strategic projects. • Manage confidential company, employee, and investor information with exceptional professionalism, judgment, and integrity. • Anticipate needs, identify bottlenecks, solve problems proactively, and create systems that improve efficiency across the CEO’s day-to-day operations.

• 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

Role Description We are seeking a meticulous Quality Assurance Engineer to join our dynamic team and take ownership of ensuring the quality and reliability of our software products. As a Quality Assurance Engineer, you will play a crucial role in designing, implementing and executing test strategies, executing test plans, and collaborating with cross-functional teams to keep and improve the automation coverage and identify and address eventual defects. This is an exciting opportunity to contribute to the development of groundbreaking insurance solutions in a fast-paced startup environment. What you’ll do - Architect Automation Frameworks: Design, develop, and maintain scalable automated testing frameworks using Playwright and TypeScript/JavaScript. - Implement Design Patterns: Apply industry-standard test design patterns (e.g., Page Object Model, Screenplay Pattern, App Actions, or Singleton) to ensure a maintainable and robust codebase. - Optimize CI/CD Integration: Integrate automated suites into CI/CD pipelines to provide rapid feedback loops for the engineering team. - Technical Collaboration: Partner with Software Engineers during the design phase to advocate for "testability" and influence the development of features from the ground up. - Advanced Locator Strategy: Develop and enforce sophisticated locator strategies to ensure test stability and reduce flakiness across dynamic web applications. - Quality Analytics: Analyze test execution data to identify quality bottlenecks in any of the application areas and provide actionable insights to the team. - Version Control Mastery: Manage test code through Git, participating in code reviews to ensure the quality of the automation suite itself. - Continuous Quality Improvement: Continuously identify opportunities to enhance testing processes and improve efficiency. - Documentation: Document test procedures, test results, and defects in a clear and concise manner. - Living Documentation & BDD: Advocate for and implement Behavior-Driven Development (BDD) using Gherkin syntax to create "living documentation." Transform requirements into executable specifications that clearly communicate test procedures, results, and defects to both technical and business stakeholders. - Strategic Manual Testing: Conduct targeted manual or exploratory testing when necessary, primarily for new feature discovery or complex edge cases that aren't yet ready for automation. - Be a Team Player: Be always proactive, participate in Agile development processes, including sprint planning, daily stand-ups, and sprint reviews. - Mentor Developers: Partner with software engineers to provide training and guidance on writing effective unit, integration, and smoke tests, elevating overall code quality and reducing downstream automation needs. - Product Roadmap Alignment: Collaborate closely with Product Managers to review upcoming features and roadmaps, proactively designing test strategies that anticipate new functionality and ensure seamless quality coverage from the outset. Qualifications - Innovative: You aren't satisfied with the status quo and constantly seek to optimize test execution time and reliability. - Growth-Oriented: You have a hunger for mentorship and staying current with the evolving JavaScript/TypeScript ecosystem. - Agile & Urgent: You balance the "keener sense of urgency" with the architectural discipline to "do it right" the first time. - Principled: You hold yourself and your code to high standards, maintaining a "do the right thing" mentality in a high-performing, non-toxic environment. - Proactive: A strong drive and desire to win together as a high-performing team. Requirements - Must haves: - Automation Expertise: Proven experience as an SDET or Automation Engineer with a special focus on Playwright and/or Serenity-JS. - QA Expertise: Proven experience in software quality assurance, with a strong understanding of QA methodologies, types of testing and best practices. - Code Foundation: Strong foundations in TypeScript and JavaScript, with the ability to write modular, reusable, and maintainable code for end-to-end, integration, and unit testing layers. - Strategic Test Design: Deep understanding of test design patterns and how to structure a test suite for long-term maintenance. - Locator Strategies: Expert-level knowledge of CSS selectors, XPath, and different locators strategies to handle complex DOM structures. - Version Control: Advanced knowledge of Git (branching, merging, pull requests). - SDLC/Agile: A solid understanding of the Software Development Lifecycle and how automation fits into a fast-paced Sprint cycle. - Analytical Mindset: The ability to debug complex failures and differentiate between environment issues, script flakiness, and genuine application bugs. - Restful APIs: Strong knowledge in testing APIs. - Communication Skills: Strong communication and collaboration skills, with the ability to work effectively in a team environment. - Nice to haves: - Python Skills: Experience with Python for scripting. - Other Automation Frameworks: Selenium, Serenity-BDD, Cypress. - Full-Stack Testing: Experience testing mobile, mobile-responsive web applications and APIs (RESTful/GraphQL). - DevOps Exposure: Experience configuring GitHub Actions, Jenkins, or similar CI/CD tools. - Performance Testing: Familiarity with load testing tools (e.g., k6 or Artillery). - Industry Experience: Prior experience in the Insurtech or Fintech sectors. - Education: A degree in Computer Science, Engineering, or a related technical field. - Virtualization: Experience with Docker, docker-compose and/or any other virtualization tool. Benefits - Generous equity packages. - Fully remote work environment. - Opportunity to work with a dynamic team in a fast-paced startup.

• 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

• 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

• 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.

• 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

• 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

Great companies don’t just build great products - they tell great stories. And as Ledgebrook continues to grow, how we show up in the market matters more than ever. From the way we communicate internally to how we engage brokers, partners, and the wider insurance community, strong marketing, communications, and events play a critical role in building our brand. At Ledgebrook, we’re building something different in the insurance industry - a modern, high-performing insuretech designed to move faster, think differently, and deliver better outcomes for our partners. That includes how we communicate and connect with the market. If you enjoy bringing ideas to life, creating memorable events, and helping a company tell its story in a clear and compelling way, you’ll fit right in. About the Role We are seeking a Marketing & Events Manager to join our growing team and help support the continued development of Ledgebrook’s brand, communications, and industry presence. As a fast-growing MGA, Ledgebrook is building a modern, high-performing organization and our communications and marketing capability is evolving alongside the business. This role will play an important part in helping us deliver high-quality internal and external communications while expanding Ledgebrook’s presence across key industry events and channels. You will work closely with teams across the company to plan and deliver communications initiatives, coordinate marketing activity, and manage Ledgebrook’s growing program of internal and external events. From industry conferences and broker events to internal communications and content development, this role will help ensure Ledgebrook communicates clearly, consistently, and effectively as we scale. This role sits within our ‘Office’ team and in addition to leading marketing and events activity, will also provide support to the executive team, coordinating priorities such as calendar and travel management. As a result, this is a highly visible, cross-functional role that requires strong organizational skills, discretion, and the ability to seamlessly balance strategic marketing initiatives with day-to-day operational support. We are looking for someone who is highly organized, proactive, and excited about working in a fast moving environment where new ideas are encouraged and ownership is valued. Ledgebrook currently operates in a fully remote work environment, so we are more focused on your experience, mindset, and cultural fit than where you physically sit. About you Here at Ledgebrook we’re passionate about creating a team that thrives on continuous learning and shares our excitement about building a company from the ground up. We’re looking for people to join us with: - 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 - we balance getting it right with getting it done right now - 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. We don’t look for blame, we look for the solution Requirements As a future Marketing & Events Manager, your experience and qualifications should include: - 3–5+ years experience in marketing, communications, events, or a related field - Experience planning and delivering corporate events, conferences, or industry engagement activities - Strong project management and organizational skills with the ability to manage multiple priorities simultaneously - Experience supporting internal and external communications, including written content and messaging - Ability to work cross-functionally with teams across the business - Strong written communication skills - A proactive mindset with the ability to anticipate needs and solve problems - High attention to detail and ability to manage logistics effectively - Experience supporting senior stakeholders or executives, including calendar management, travel coordination, or administrative support Benefits - Competitive salary and meaningful equity ownership - Health Insurance 100% employer-paid option available - Additional benefits available include 401k plan, dental, vision & other options - Remote work, flexible hours - Unlimited time off policy