Enstar Group

Role Description The Investments Senior Associate, Alternatives Forecasting & Portfolio Intelligence is the dedicated analytics, forecasting, and performance expert for the Alternatives and Non-Core portfolio spanning Private Equity, Private Credit, Real Estate, Infrastructure, Hedge Funds, and Non-Core asset classes. The role translates portfolio data, performance, cash flow forecasts, and market intelligence into actionable insights supporting strategic asset allocation, M&A pricing, portfolio construction, and executive decision-making. The role owns: - Asset- and strategy-level cash flow, NAV, and return forecasting - The Alternatives segment of the investment financial plan - M&A pricing projections for alternative assets - Long-term strategic asset allocation inputs for alternatives - Performance attribution, variance analysis, and non-core benchmarks - Portfolio risk and exposure reporting - Fee and expense analytics - Enstar’s alternatives data infrastructure, including Power BI dashboards and key external platforms such as SPI by StepStone and Canoe Qualifications - 6+ years of experience in a quantitative investment analytics, portfolio analytics, investment forecasting, or alternatives-focused role at an institutional investment organization, asset manager, alternative investment firm, or investment bank - Prior experience in a dedicated alternatives analytics, portfolio data, or investment forecasting function; experience within an insurance company investment environment strongly preferred - Demonstrated experience building and maintaining asset-level forecasting models for illiquid asset classes - Experience with performance measurement, attribution, and custom benchmark construction for alternative investments - Experience with large investment datasets using SQL, Power BI, Excel, and related analytics tools - Experience with alternatives-specific data platforms and reporting tools - Strong written and verbal communication skills - Demonstrated ability to automate and scale analytical processes - Bachelor’s degree in finance, economics, mathematics, statistics, computer science, or a related quantitative discipline required; Master’s degree preferred - Progress toward CFA and/or CAIA designations is preferred - Familiarity with alternative asset classes - Deep understanding of alternative fund structures, cash flow mechanics, NAV and capital account reporting, fee structures, and their implications for portfolio modelling - Deep understanding of alternatives performance measurement - Knowledge of strategic asset allocation frameworks and capital market assumption development - Knowledge of portfolio risk analytics concepts - Expert proficiency in Excel for financial modelling - Proficient in leveraging Excel Cube Functions and Power Pivot data models - Advanced Power BI skills - Strong project management and organizational skills - Experience applying AI-enabled tools, automation platforms, or data engineering workflows - Collaborative team player - Self-starter with intellectual curiosity Requirements - Develop and maintain asset- and strategy-level forecasts, financial plans, and M&A pricing models for all alternative and non-core investments - Provide performance attribution, actual vs. budget variance analysis, and benchmarking for the alternatives and non-core investments portfolio - Develop and maintain long-term capital market assumptions and strategic asset allocation inputs for alternative asset classes - Serve as the subject matter expert for alternatives portfolio analytics and exposure reporting - Build and maintain a suite of Power BI dashboards and lead alternatives data management across internal and external systems - Drive continuous enhancement of forecasting and analytics capabilities - Work in close coordination with the Portfolio Forecasting & Investment Analytics function - Gather input from internal and external managers and vendors; update forecasts on a quarterly, semi-annual, annual, or as-needed basis - Lead the annual liquidity survey across the Alternatives portfolio - Develop, maintain, and update investment projection models for individual alternative and non-core assets - Run quarterly and annual planning cycles in partnership with the broader Investments team - Analyze and explain quarterly asset class returns against assigned benchmarks - Quantify and explain the variance of quarterly investment results against the annual budget - Develop, build, and maintain custom benchmarks for each alternatives asset class - Lead requests to produce and analyze portfolio exposures - Prepare analytics, attribution, forecasting, and portfolio materials supporting Investment Committee discussions - Build, develop, and maintain fee estimation models for assigned assets - Aggregate, analyze, and present total fees and expenses paid to alternative investment managers - Maintain historical fees and expenses data and related Power BI reporting - Build and maintain a suite of interactive performance, forecasting, fee, risk, and portfolio analytics dashboards in Power BI - Lead data management for Alternative Investments across internal and external systems - Act as business owner for alternatives analytics platforms and reporting infrastructure - Oversee the setup, configuration, and ongoing maintenance of key external platforms - Deliver additional analyses, models, and special projects as business needs dictate Benefits - Best-in-class Medical, Dental, and Vision healthcare for single and family coverage - Board-certified doctors and pediatricians available virtually 24/7 for urgent care - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA) - Access to Dependent Care FSA to cover daycare expenses - Access to Employee Assistance Programs (EAP) for health and well-being - Optional Pet & Home/Auto Insurance - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses) - 401K retirement plan (company matches up to 6% of employee contribution) - One paid annual volunteer day

Role Description As part of the HR Shared Services Team, the HR Services Coordinator will deliver first-line support and day-to-day activities for the HR Team. The individual will respond to employee enquiries and leadership requests. - Provide administrative support to the (US) - Maintain accurate and current electronic personnel files and documentation in compliance with applicable legal requirements and Company policies as well as country-specific legislation - Partner with the HR Business Partners and HR Centres of Expertise to support the delivery of HR Target Operating Model - Assist with onboarding by preparing contracts/offer letters, new joiner documentation, background screening and country-specific processes - Coordinate and deliver new hire orientation/onboarding activities - Assist with assigning and follow-up of mandatory training through Enstar’s Learning Management System - Provide first-line support and escalation for HR systems - Process changes to employee records within Enstar’s HRIS including new joiners, job changes and leavers - Prepare employee changes and termination paperwork, notifications and change forms - Answer frequently asked questions from employees concerning HR processes - Support inquiries and requests related to the HR department - Continuously remain up to date on global HR practices - Assist with HR projects as necessary, including but not limited to HR data audits, new policy and program development - All other duties as required Qualifications - Self-directed individual with initiative, analytical and problem-solving skills - Customer focus, collaboration and teamwork - Ability to exercise practical judgment, sensitivity, creativity to changing needs and situations - Ability to operate in a fast-paced organization and handle multiple projects simultaneously - Ability to work as part of a wider team and independently - Strong Microsoft Office skills in Outlook, Word, PowerPoint, and Excel - Experience using HR & Payroll platforms - Initial experience gained within a HR department - Providing system support to users - Involvement in system development or enhancement - Proven ability in creating management information for the business - Strong organizational skills that reflect ability to perform and prioritize multiple tasks and a complex workload seamlessly with keen attention to detail and follow-up - Experience working in a fast-paced environment and ability to apply good work habits to effectively complete assigned tasks and contribute to the smooth operation of the department - Ability to work effectively in a team environment and to collaborate/work remotely with colleagues - Excellent verbal and written communication skills Benefits - Enstar offers best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians are available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses, i.e., gym memberships, massage, etc.). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Role Description Responsible for addressing all claim issues related to Assumed Accounts assigned by gathering information necessary to make informed and responsible decisions to bring claims to appropriate resolution. Key Accountabilities - Within established authority administers claims for assigned Assumed accounts. Conducts coverage verification, investigation, evaluation, reserving and authorization of claims payments and recovery. - Manage claim activity and monitor all claim development for assigned accounts. - Alert Management of significant loss development/activity. - Evaluate and investigate claims to confirm coverage and identify any potential issues. - Ensure proper reserving of reported claims through utilization of additional case reserves, proper documentation and disposition of individual excess of loss and pro rata accounts. - Ensure timely processing of claim transactions. - Ensure accuracy of processed claims payments. Coordinates with operations and accounting to confirm processing of prompt payments. - Maintain accurate data of payments, reserves, scanned documents, new mail, etc. - Maintain integrity of imaged claim files and maintain a diary system for assigned files. - Analyze and produce reports highlighting large losses, coverage and critical issues for review by claims management and actuarial. - Produce and analyze specific account data and generate reports in preparation for claim audits. - Support reinsurance audits which will utilize the specialized skill developed during this person’s career to understand whether complex claims have been handled and ceded appropriately. - Work with external customers to address questions, resolve problems and maintain rapport. - In addition to the above key responsibilities, may be required to undertake other duties from time to time as the Company may reasonably require. Qualifications - Bachelor’s degree. - 10+ years claims analysis experience with a Reinsurance/Insurance Carrier. - General understanding of legal principles as they pertain to reinsurance claims. - Requires experience across various lines of business, including GL, Property, Auto and WC. - Requires the ability to understand the various reinsurance agreements which govern these lines of business, as well as the ability to comprehend complex loss presentations received by ceding companies. - Ability to work independently. - Ability to follow instructions, respond to management direction and solicit feedback to improve performance. - Ability to demonstrate accuracy and thoroughness, monitor own work to ensure quality and apply feedback to improve performance. - Ability to adapt to changes in the work environment, manage competing demands and is able to deal with frequent change, delays or unexpected events. - Ability to identify and resolve problems in a timely manner, gather and analyze information with good attention to detail. - Detail oriented. - Organizational skills. - Ability to multi-task. - Computer skills (Microsoft applications). - Excellent written and verbal communication skills. Benefits - Enstar offers best-in-class bundled Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians are available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses, i.e., gym memberships, massage, etc.). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Role Description The Investment Associate partners with the VP - Alternative Investments, and the Non-Core Investments team to support manager selection, monitoring, reporting, forecasting, and operational activities across the Alternatives and Non-Core portfolios. - Monitoring external managers and underlying investments - Delivering monthly, quarterly, and annual reporting - Building and maintaining asset models and financial projections - Supporting portfolio management, performance analysis, and stakeholder reporting - Conducting manager due diligence and preparing evaluation and recommendation materials - Delivering ad hoc analysis and project support to inform investment decision-making Enstar manages relationships with more than 30 external managers across Alternatives (Private Equity, Private Credit, Real Estate, Infrastructure, and Hedge Funds) and Non-Core (High Yield, Public Equity, and CLO Equity) asset classes. These portfolios are targeted to represent approximately 30% of Enstar’s roughly $20 billion in investable assets and are expected to contribute a significant portion of projected investment returns. What you will be doing - Ongoing Monitoring of Existing Managers and Investments - Support initial and ongoing relationships with assigned managers; take meeting notes; summarize presentations; draft and circulate monitoring notes and quarterly investment updates; and ensure the accuracy of existing ratings. - Analyze and explain absolute and relative performance; assess results against budget, assigned benchmarks, and peer groups. - Maintain scorecards for funds, strategies, and managers using both qualitative and quantitative analysis. - Develop and maintain peer group comparisons for existing and prospective managers and strategies. - Maintain accurate and up-to-date mandate, manager, and investment data across internal databases and third-party systems. - Manager Due Diligence - Support RFP development and end-to-end due diligence for current and prospective managers and funds. - Contribute to investment memoranda and supporting analysis for Investment Committee review. - Portfolio Management and Reporting - Onboard new managers and investments in coordination with regional investment teams, Legal, Investment Accounting, Investment Operations, IT, external managers, and vendors; ensure internal systems and databases are updated with complete and accurate manager and investment data. - Develop, maintain, and update NAV, cash flow, gain/loss, and return projection models for assigned investments and managers. - Reconcile portfolio holdings to Investment Accounting reports and perform data integrity checks across multiple systems, including Clearwater, BNY’s NEXEN, StepStone Omni, Canoe, and Power BI. - Prepare quarterly materials for the Group Investment Committee, Board of Directors, and CIO. - Update and enhance reports built in Power BI and Excel. - Coordinate with custodians and vendors on fund setup; ensure all funds are reflected in upstream systems in a timely manner; and work with vendors and counterparties to transfer holdings between accounts and legal entities. - Ad Hoc Projects - Deliver additional analysis and special projects on an ad hoc basis as business needs dictate. Qualifications - A minimum of 2–4 years of experience in an institutional investment role focused on the due diligence, monitoring, and reporting of external managers, with an emphasis on the alternative strategies noted above. - Experience within an insurance company environment—such as an investment general account, CIO office, or insurance asset manager—is strongly preferred. - Experience screening, conducting due diligence on, and monitoring external alternative funds and managers is required. - Bachelor’s degree required; master’s degree preferred. - Progress toward the CFA and/or CAIA designation is preferred. - Understanding of non-core and alternative asset classes, including private credit, private equity, real estate, infrastructure, hedge funds, public equity, CLO equity, and high yield. - Solid understanding of statistical concepts, methods, and models and their application to investment analysis. - Knowledge of performance measurement, attribution, and benchmark construction. - Knowledge of alternative investment performance measures and metrics, including TVPI, DPI, IRR, TWR, unfunded commitments, and exposure. - General understanding of investment management, strategic and tactical asset allocation, and capital markets. - Proficiency in Excel modeling and the quantitative skills required for asset modeling, performance attribution, and reporting. - Strong skills in PowerPoint, Word, and Bloomberg, with familiarity with StepStone Omni, MSCI Private I, or similar alternative investment platforms. - Ability to manipulate large data sets and translate them into actionable insights using Excel (including pivot tables) and/or Power BI. - Ability to develop new portfolio and investment results exhibits that are clear, concise, and easily digestible for senior management and other decision-makers. - Strong written and verbal communication skills. - Strong ability to collaborate effectively across functional areas. Benefits - Enstar offers best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians are available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses, i.e., gym memberships, massage, etc.). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Role Description The Director of Investment Accounting is responsible for leading the investment accounting, reporting (external, regulatory & client), and analysis of Enstar’s investment portfolio, as well as providing technical expertise related to investment transactions. This role will focus on the integration of M&A transactions and recommend and drive process improvements. What you will be doing - Leadership & Management - Assist with leading, mentoring, and developing a high-performing investment accounting team, fostering a culture of accountability, collaboration, and continuous improvement. - Oversee daily, monthly, and quarterly close activities related to investment accounting and reporting, ensuring accuracy, timeliness, and strong internal controls. - Manage relationships with internal partners and external auditors. - Work closely with the VP of Investment Accounting to ensure depth of knowledge for all critical processes. - Investment Accounting, Reporting & Analytics - Oversee accounting, and financial and regulatory reporting for all investment asset classes, which may include fixed income securities, structured products, public and private equity, derivatives, mortgage loans and real estate, alternative investments (primarily fund investments, rated note structures). - Review VIE analysis and consolidation conclusions. - Own the accounting and reporting of our private equity portfolio. - Ensure compliance with applicable accounting guidance (e.g., US GAAP, Statutory Accounting Principles, or other frameworks as applicable). - Review financial statements, footnotes, and management reporting. - Ensure accuracy and completeness of investment-related disclosures for regulatory filings. - Maintain and enhance internal controls. - Oversee pre and post-close portfolio analytics, report on investment-related KPIs. - Partner with internal teams as necessary (FP&A, Investment Management, and Reporting teams) to support BAU and strategic initiatives. Qualifications - Bachelor’s degree in Accounting, Finance, or related field required. - CPA or equivalent qualification preferred. - 10+ years of investment accounting experience. - Strong knowledge of complex investment products and related accounting standards. - Prior leadership and team management experience. - Experience working in an entrepreneurial, fast-paced environment. - Experience with Clearwater and Canoe preferred. - Advanced Excel/Alteryx skills preferred. - Deep expertise in US GAAP, SAP, Solvency, and BMA investment accounting and reporting. - Strong analytical, problem-solving, and technical accounting skills. - Experience with investment valuation, CECL/impairments, cash flows. - Excellent communication and business partnership skills. - Proven ability to lead change and drive process improvements. - Ability to respectfully challenge the current state and recommend improvements. - Ability to work in a fast-paced environment and manage multiple tasks and deadlines. Benefits - Enstar offers best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians are available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses, i.e., gym memberships, massage, etc.). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Role Description The Senior Associate II, Investments is a key member of Enstar’s Investments Team, supporting the Regional CIOs and broader Investments function through portfolio analytics, forecasting, and investment decision support. The role develops and maintains the models and analytical frameworks that underpin asset allocation, investment budgeting, M&A pricing, performance measurement, and portfolio forecasting across Enstar’s ~$20 billion global investment portfolio. Working closely with senior investment leadership, the role helps inform portfolio construction and investment decisions across Enstar’s operations in Bermuda, the United States, and the United Kingdom. What you will be doing Primary Responsibilities: - Strategic & Tactical Asset Allocation Analytics: - Develop and maintain the inputs to the portfolio optimization process, including: - Maintaining capital market assumptions, such as expected returns, volatilities, and cross-asset correlations. - Incorporating capital, risk, and liquidity constraints from other functional areas. - Supporting the development of relative value analysis across asset classes to inform tactical positioning decisions. - Investment Forecasting & Budgeting: - Build and maintain the projections behind the firm’s investment budget and longer-term investment outlook, including: - Calculating net investment income and total investment return across multiple time horizons (e.g., 1-year and 5-year forecast). - Integrating new business and liability/claims projections from Actuarial. - Developing reinvestment assumptions. - Incorporating pacing projections for alternative assets, including NAV, gain/loss, and cash flow by asset class. - Developing bands around the base case forecast based on statistical analysis. - Working with FP&A, Treasury, and Capital Management to reconcile these forecasts with the broader financial plan. - M&A Pricing Model Enhancement & Maintenance: - Own and continuously enhance the M&A pricing model used by the regional investment teams to price prospective acquisitions, including: - Updating the model with new market data on a regular basis. - Incorporating new investment strategies for use in deal pricing. - Expanding model functionality for new requirements from the M&A and regional teams. - Performance Measurement & Attribution: - Track and explain actual investment results against budget, produce performance attribution by asset class, and prepare the supporting analysis for investment committee and board materials. Secondary Responsibilities: - Reporting & Visualization: - Maintain and enhance the recurring analytics, dashboards, and presentation materials used to communicate portfolio results to senior management, investment committees, and boards. - Exposure, Risk & Benchmarking: - Maintain portfolio exposure, monitor risk analytics, and measure asset-class benchmarks used to evaluate performance. - Data & Tooling: - Maintain the models and analytical tools the regional teams rely on. - Cross-Functional Support: - Provide analytical support to Tax, Accounting, Legal, Regulatory, Actuarial, Capital Management, and Treasury on portfolio-related questions. - Integration of Non-Core Projections: - Work in close coordination with Alternatives Forecasting & Portfolio Intelligence function supporting non-core projections to deliver integrated, firm-wide investment insights. Qualifications - 6+ years of experience in investment forecasting, portfolio analytics, asset allocation, portfolio strategy, or a quantitative investment role. - Demonstrated experience building and maintaining asset-level forecasting models. - Understanding of investment management, capital markets, strategic and tactical asset allocation, and portfolio construction. - Strong quantitative and analytical skills, including the ability to manipulate, validate, and analyze large and complex investment datasets. - Strong understanding of fixed income markets, portfolio construction, and investment risk metrics. - Strong written and verbal communication skills. - Demonstrated ability to automate and scale analytical processes through programming, data modeling, or workflow design. - Experience using Python, SQL, VBA, or similar tools to automate investment analytics and forecasting processes. - Undergraduate degree in finance, economics, statistics, mathematics, or a related quantitative discipline. Requirements - Experience building analytical tools and investment models within an insurance company, insurance asset manager, or other insurance-focused investment organization. - Familiarity with alternative asset classes, including performance measurement, pacing projections, and cash flow forecasting. - Familiarity with insurance regulatory regimes across Bermuda, the United States, and the United Kingdom. - Experience with investment-related platforms such as Clearwater, MSCI Risk Manager, Arcesium, and Bloomberg. - Experience applying AI-enabled tools, including LLMs, automation platforms, or quantitative research workflows. - Experience with Power BI or similar business intelligence and visualization tools. - CFA designation, progress toward the CFA charter, and/or an advanced degree in a relevant field. Benefits - Best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Role Description The Senior Claims Examiner is responsible for adjusting claims and/or providing TPA oversight of the various entities under management. The role requires the ability to deal with a wide range of losses including high value and complex claims. The examiner, with minimal oversight, will lead and direct junior examiners, TPAs, and vendors. The role is responsible for performance, development, and coaching to maximize performance. Key Accountabilities / Deliverables - Ensure implications for stakeholders, particularly policyholders, are considered in business approaches to deliver fair customer outcomes. - Adjust claims via paper or electronic presentations for all Syndicates and/or Group Companies. - Investigate, evaluate, negotiate, and adjudicate claims within authority, meeting or exceeding Claims Policies and Procedures. - Assist with initial triage, onboarding reviews, and scheduling of roundtable discussions. - Provide coaching, feedback, and direction on claims. - Manage the Claim Status Report documentation process. - Ensure all data is concise and accurate in electronic claim systems. - Use electronic diary systems to manage all claims. - Utilize data including loss runs to manage claims. - Set appropriate and accurate case reserves in accordance with the company’s reserving philosophies. - Manage attorneys and negotiate and liaise with co-insurers. - Negotiate settlements as part of the market and proactively identify and progress direct settlements for Enstar companies. - Report claim developments and account information to management and the Litigation Legal team as applicable. - Interpret contracts, manage cedant relationships, and legal representation. - Conduct inspections of records when required and negotiate equitable claim resolutions. - Monitor and oversee external agreement parties against SLAs and report any performance issues to Management. - Comply with Enstar claims handling authority levels. - Support and assist Outwards, Commutation, and Complex Claims teams as required. - Carry out duties within internal policies and procedures in accordance with applicable law, rules, regulations, and Enstar’s shared values. - Work with external customers to address questions, resolve problems, and maintain rapport. - Assist with the Reinsurance reporting process. - Maintain applicable adjuster licensing. - Serve as the lead and primary point of contact for TPAs and vendors. - Resolve complex claims issues and disputes. - Provide analysis of claims data, metrics, and results from TPA performance. - Provide periodic reports to management. - Coordinate claim reviews and provide data summaries. - Drive the performance management process for TPAs. - Maintain transparent communication with TPAs through meetings, emails, and regular communications. - Manage corporate expenses by monitoring file allocations, resources, and other expenditures. - Ensure compliance with all legal, regulatory, and internal control requirements. - Provide claims insights to assist other business units by collaborating on data analysis and trends. - Maintain professional and technical knowledge by attending educational workshops and participating in professional societies. Qualifications - Technical knowledge of Property & Casualty claims. - Significant experience (8+ years) in adjusting claims relevant to the classes of business handled. - Good knowledge of contract wordings, coverage, and reinsurance structures. - Detailed understanding of good faith claims handling. - Working knowledge of State specific Claims Handling Guidelines. - General understanding of legal principles as they pertain to insurance claims. - Bachelor’s degree preferred. - Ability to serve as a resource, train, and mentor junior staff. - Analytical skills. - Knowledge of insurance regulations and industry best practices. - Ability to work independently. - Excel proficiency. - Experience managing a Casualty and/or Professional Liability portfolio preferred. - Exposure to participation in due diligence reviews preferred. - Presentation skills. - Understanding of actuarial concepts. Benefits - Best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Role Description Investments Senior Associate will support and work together with regional CIO, Investments and the Investments team to: - Monitor the existing investment portfolios to ensure that portfolio allocation is in line with strategic and tactical allocation preferences while operating within the constraints of a regulated insurance company. - Construct optimal investment portfolios and return streams as an input to the M&A pricing process. - Generate new strategic and tactical ideas for implementation in the portfolio. - Diligence new asset managers and monitor existing asset managers. - Provide reporting for local and group Board of Directors, investment committees, rating agencies and regulators. Qualifications - 5-10 years of experience in insurance company asset management. - Thorough understanding of investment management, strategic asset allocation, tactical asset allocation and capital markets, preferably within the context of insurance asset management. - Good understanding of the portfolio construction process required in order to make asset allocation decisions. - Extensive experience working with external asset managers (or internal portfolio managers) in development of benchmarks, asset allocation, and efficient frontiers. - Bachelor’s degree required, Master’s degree preferred. - Chartered Financial Analyst (CFA) qualification is preferred. - Applicable experience and understanding of core fixed income asset classes as well as non-core asset classes, including public equity, private equity, real estate, hedge funds, infrastructure, CLO equity, high yield, bank loans, emerging market debt, and other investments. - Understanding of capital markets and insurance company portfolio management. - Knowledge of Bermuda BSCR capital regime is preferred. - Excellent quantitative skills required for the portfolio construction and risk measurement processes. - Strong verbal and written communication skills are required for presentations to senior management and external stakeholders. - Ability to prioritize commitments and time management is a significant requirement, given the nature of our operations. - Ability to use Excel and PowerPoint is critical, given the requirement to develop investment analytics and proposals. - Knowledge of Python, PowerBI, SQL, and/or other programming languages is preferred. - Strong collaborator with other functional areas and executive management to ensure consistency and efficiency of approach. Requirements - Partner with regional CIO and the Investments team regarding the following accountabilities: - Portfolio Construction for M&A Targets – Provide analysis for internal deal from review of the existing target acquisition portfolio, suggested portfolio repositioning, and portfolio yields. - Strategic Asset Allocation and ALM – Develop and maintain strategic asset allocation for existing portfolios. - Budgeting & NII Projections – Partner with regional CIO monitoring actuals vs. budget throughout the year. - New Idea Generation and Proposal Development – Actively evaluate current market conditions and develop investment recommendations. - External Manager Diligence – Manage initial and ongoing relationships with core fixed income and specialty asset external managers. - External Manager Performance Measurement and Monitoring – Help establish benchmarks and review manager performance vs. benchmarks. - Regional Board of Directors/Investment Committee Presentations – Prepare quarterly investment performance presentations. - Compliance – Monitor compliance with internal and external portfolio constraints. - Cash Management – Work with regional portfolio management team to ensure excess investable cash balance is minimized. - Market Color – Provide regular written updates on interest rate, credit, and equity markets and macroeconomic news. - Portfolio Reporting – Responsible for drafts of monthly portfolio performance estimate and quarterly investment update presentations. - Investment Expertise – Possess specialized depth and/or breadth of expertise in a particular Investment field. - Project Management – Project management responsibilities on several projects. - Investment Research - Present research at senior investment morning calls. Benefits - Enstar offers best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians are available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Role Description Reporting to the Group CRO, The Group Head of Exposure Management is responsible for establishing and leading a centralised Exposure Management (EM) function, providing a single, authoritative view of underwriting exposure across the Group. This role is critical to ensuring that underwriting growth is supported by robust aggregation, visibility and control of tail and correlation risks. - Establish and lead the Group Exposure Management function, including defining the target operating model, governance and roadmap. - Build, lead and develop a high‑performing technical team. - Act as the central authority for underwriting exposure aggregation across the Group. - Maintain a consolidated, forward looking view of exposures across entities, geographies and perils. - Oversee key exposure metrics and stress scenarios. - Monitor concentrations and escalate risk appetite breaches. - Provide independent exposure and tail risk assessments for material transactions. - Quantify incremental portfolio, aggregation and correlation impacts. - Ensure appropriate data granularity and modelling standards pre-bind. - Deliver exposure reporting to senior management, CRO and Risk Committee. - Provide regulatory reporting and post event impact assessments. - Escalate material changes in exposure or risk profile. - Oversee application and calibration of exposure and catastrophe models (incl. external cat model vendors). - Define and enforce exposure data standards and model governance. - Ensure consistency of assumptions and methodologies across the Group. - Partner with Underwriting / AFG, M&A, Reserving, Capital Modelling and Reinsurance to inform risk based decisions. - Act as the primary exposure risk contact for executive management and the Board Risk Committee. - Provide clear, actionable insight to support strategy and portfolio steering. - Lead phased development of EM capabilities. - Embed exposure management into underwriting, M&A, reinsurance and capital decisions. - Drive continuous improvement in tools, processes and analytics. - Coach and develop team members in line with Enstar policies. - Take a continuous improvement approach, helping evolve processes, outputs and responsibilities over time in line with business needs and professional development. Qualifications - Significant experience (12+ years) in exposure management, catastrophe modelling within a (re)insurance environment. - Proven leadership experience, including building and managing high-performing technical teams. - Strong track record engaging senior stakeholders, including executives and boards. - Deep expertise in catastrophe modelling, exposure aggregation and tail risk analytics. - Strong knowledge of vendor models (e.g. RMS, AIR) and exposure data structures. - Strong quantitative and analytical skills, with ability to translate complex outputs into clear insights. - Ability to link exposure insights to underwriting, reinsurance and capital decisions. - Experience supporting transactions and portfolio construction. - Strong communicator across technical and non-technical audiences. - Confident providing independent challenge and escalation. - Ability to operate effectively across a global, matrixed organisation. - Pragmatic and delivery-focused, able to balance long-term build with immediate business needs. - Collaborative, with strong relationship-building skills across functions. - High level of ownership, accountability and professional judgement. Benefits - Best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses, i.e., gym memberships, massage, etc.). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.

Role Description The Senior Associate I, Portfolio Analytics, will support the ownership of data and analytics used across Enstar’s Core and Alternative Assets. This includes working with internal and external data sources, identifying critical elements within these sources, transforming the data into a usable format, and loading it into quantitative models for Enstar’s investment portfolio analytics. Key Accountabilities / Deliverables - Core Investment Analytics Responsibilities: - Capturing and transformation of data from various sources (Clearwater, MSCI, Bloomberg, Excel, CSV files, etc.) within the Investments data warehouse platform (Arcesium) and producing an Investments Book of Record (“IBOR”). - Supporting modelling of core/non-core assets for performance measurement (including benchmarking and attribution). - Look-through analysis of Fund of Funds. - Implementing various dashboards within Fabric or Power BI in support of Investments Team reporting processes. - Alternative Investment Analytics Responsibilities: - Alternative investments data capture, workflow/deal management, and building analytics within Power BI/Fabric model. Job Responsibilities - Core Portfolio: - Develop, maintain, and validate pipelines for ingesting core assets data within the Arcesium data platform. - Transformation of data to produce IBOR for supporting/producing core asset analytics. - Alts Portfolio: - Develop, maintain, and validate Power BI datasets/dataflows for Alternative Investments within Fabric. - Support and enhance the current process of code changes, deployments, and production support, responding to critical business queries. - Liaise with key stakeholders - Vendors, Regional and Alternative Investment Teams, Risk, Capital Management, Investment Accounting, and Treasury for investment-related data and forecasts. - Develop & maintain reports/dashboards/paginated reports that capture key Investment analytics for Board and Investment Committee (“IC”) materials. - Build, maintain, and enhance the Investments Data warehouse (Arcesium) for ingesting data of core assets from various stakeholders. - Work in close coordination with the Alternatives and Non-Core Specialty Mandates team to provide analytical and quantitative solutions for Alternatives and Non-Core investments. - Support Head of Investment Operations & Reporting in achieving the Investment team’s overarching mission of identifying, modelling, measuring, and reporting of the investment portfolio strategy, positioning, and performance. - Build, maintain, and enhance existing Power BI power queries, DAX measures, datasets, dataflows, online and paginated reports, and dashboards for Alternatives and Core assets. - Optimize Alternative investments data pipelines and ensure data quality is pulled from multiple sources into our cloud-based Investment Data and Analytics Platform. - Provide solutions to capture, track, and update security master information, commitments schedule by entity, fund documents, call notes, fund returns, manager scorecard data, monitoring status, statement status, compliance status, etc., on private equity funds, co-investments, hedge funds, and long-only funds. Qualifications - 3-5 years relevant experience in computer or software engineering, applications/systems development, data engineering, data science, data analysis at an investment manager/insurance company, pension plan, endowment, custodian, fund administrator, investments system vendor, investment consultant or financial services firm. - Bachelor's Degree in Computer Science, Engineering, Math, Finance, or Science. - Strong technical, analytical, and communication skills. - Fluent in dimensional and data modelling. - Working knowledge of Advanced SQL and building pipelines for ETL processes. - Demonstrable experience and knowledge of Power BI development, including Power Query and Dataflows, designing Power BI datasets, and highly proficient in writing DAX measures. - Data visualization skills in Power BI and demonstrated experience with Conditional Formatting, Tool Tip pages, Drill Through pages, Bookmarks, and Buttons, etc. - Proficiency with Advanced Excel, MDX or CUBE Functions in Excel (CUBSET, CUBEVALUE, CUBEMEMBER), and experience setting up Excel dashboards connected to Power BI datasets. - Exposure to General Asset management for the Insurance industry with knowledge on risk metrics, performance analysis/attribution. - Functional knowledge of alternative investments and analytics such as Commitments, NAV, TVPI, DPI, IRR, Time Weighted Returns, etc. will be a plus. - Proficiency in data storage, query, and reporting/analytics optimization. - Comfortable creating business and technical requirement documents, conducting technical impact analysis, creating development estimates, and assessing project risk. - Ability to read, write, and develop to technical requirements. - Ability to coordinate with external vendors, asset managers, IT support. - Ability to partner closely with Technology, Finance, Treasury, and other functional teams across the company. - Experience with paginated reports (Report builder). - Experience with advanced scripting in Tabular Editor 2.0, and knowledge of DAX Studio is a plus. - Experience with VBA, SQL, Python, SSRS, SSIS and/or other data analysis/programming languages a plus. - Ability to work collaboratively with cross-functional teams and departments. - Ability to prioritize, manage, and execute on multiple projects in a high-performance, collaborative environment. - Detail-oriented approach and demonstrated track record of problem-solving in a team-based, results-focused environment. - Passion for continuously improving existing capabilities and a strong desire to help support business growth. - Excellent communication skills. - Progress towards CFA or CAIA is a plus. - Prior experience/exposure working with the Arcesium Data platform (Aquata) is a plus. - Familiarity with the Clearwater accounting system is a plus. Benefits - Enstar offers best-in-class Medical, Dental, and Vision healthcare for single and family coverage. - Board-certified doctors and pediatricians are available virtually 24/7 for urgent care. - Access to Health Savings Account (HSA) or Flexible Spending Account (FSA). - Access to Dependent Care FSA to cover daycare expenses. - Access to Employee Assistance Programs (EAP) for health and well-being. - Optional Pet & Home/Auto Insurance. - Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses, i.e., gym memberships, massage, etc.). - 401K retirement plan (company matches up to 6% of employee contribution). - One paid annual volunteer day.