[Hiring] Senior Associate II, Investments-Portfolio Forecasting and Investment Analytics @Enstar Group

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.