Senior Associate II, Investments-Portfolio Forecasting and Investment Analytics

Although we prefer candidates from the NY Metro area, we are also open to East Coast candidates interested in working remotely. 

About you and the role:

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. This includes:
• Maintaining capital market assumptions, such as expected returns, volatilities, and cross-asset correlations,
• Incorporating capital, risk, and liquidity constraints from other functional areas, and
• 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. This includes:
• 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, and
• 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, keeping it accurate and adaptable as deal structures and asset classes evolve. This includes:
• Updating the model with new market data on a regular basis,
• Incorporating new investment strategies for use in deal pricing, and
• Expanding model functionality for new requirements from the M&A and regional teams.
• Collaborate with Alternative Investments analytics function to ensure that Alternatives and non-core assets are modeled accurately.
• 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.

What you will bring:

Required 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, with experience supporting portfolio optimization, asset allocation analysis, and investment decision-making processes.
• Strong quantitative and analytical skills, including the ability to manipulate, validate, and analyze large and complex investment datasets, build forecasting models, perform scenario analysis, and apply statistical or quantitative techniques to investment-related questions.
• Strong understanding of fixed income markets, portfolio construction, and investment risk metrics.
• Strong written and verbal communication skills, with the ability to translate complex analyses into clear insights for investment committees, boards, and senior management.
• 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.

Preferred Qualifications

• 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, as well as rating agency capital models.
• 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, to improve investment analytics, forecasting, reporting, or data management processes.
• 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.

Your 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.

General Info 

The target base salary pay range for this role is $152,000-$160,000*

*Target full-time equivalent base salary range is based on relevant market data. The actual salary offered will depend on applicable market data for hiring location and relevant candidate knowledge, skills/experience. This salary range is not inclusive of applicable discretionary incentives.

Who we are:

We are a trusted global re/insurance group and the leading provider of retrospective solutions, with specialist underwriting capabilities. We help our clients manage risk, unlock capital and create the financial freedom to grow. With operations across the world’s major insurance hubs and a global network of close to 800 talented professionals, we bring expertise and fresh thinking to some of the industry’s biggest challenges. 

For more information about Enstar, visit our website: www.enstargroup.com. 

For more information about careers at Enstar, visit our LinkedIn Life page or visit our careers site

Why Enstar:

Learning and development are a fundamental part of every employee's career journey with Enstar. Supporting growth and career progression is key to how we engage our people - helping them to learn, grow and succeed at Enstar.  

We offer a range of initiatives and resources to support our people throughout their careers: 

• Professional Qualifications and Study Support: We support employees who wish to take professional qualifications aligned to their role and career development.  

• Training, Conferences & Seminars: As a global organisation, we work with many professional bodies to provide access to training programmes, conferences, seminars and continuing professional development (CPD) opportunities. 

• Digital Learning Hub: Our digital learning hub, LinkedIn Learning, offers a wide range of self-serve resources, including courses, videos, eBooks, and audio books, to help employees build news skills and deepen their knowledge. 

We also invest in physical, mental and financial wellbeing initiatives for our employees. Supportive teams, inspiring work and a positive working environment all contribute to our collective wellbeing. Beyond the workplace, we strive to make a positive influence in our communities and to continuously reduce our impact on the environment. 

Enstar Inclusivity Policy:

We’re an equal opportunity employer and believe that our inclusive environment creates an authentic working culture. We don’t discriminate on the basis of age, physical or mental disability, gender reassignment, marriage and civil partnership, pregnancy and carer status, race (including colour, nationality, and ethnic or national origin), religion or belief, sex and sexual orientation. Enstar is committed in providing an accessible recruitment experience for all those interested in working with us. Please let your Enstar Recruitment Partner know if you require any reasonable accommodation during the application process due to a disability to enable you to fully participate in our recruitment process.