Head of Investments - Insurance

JSS are pleased to be partnered with a growing UK-based reinsurance business, operating in a specialist area of the Property & Casualty (P&C) and Life Insurance markets. As a nimble and focused organisation outside of the large-brand landscape, they offer a unique environment: entrepreneurial, mission-driven, and intellectually rigorous. With approximately £7.2 billion in assets under oversight, they partner with leading external investment managers and are committed to strong governance, strategic agility, and long-term value creation.

Role Overview

We are seeking an experienced and proactive Head of Investments to work closely with the CIO to shape, execute, and challenge the firm's investment strategy. This role is critical to the continued evolution of their investment thinking and responsible for oversight of outsourced portfolios, manager relationships, and strategic asset allocation decisions.

You will bring deep technical investment knowledge, strong insurance industry insight, and the confidence to push beyond the status quo — asking not only “Are we doing this well?” but “What else should we be doing?”

Key Responsibilities

Strategic Leadership & Execution

• Partner with the CIO to evolve and implement the company’s investment strategy across P&C and Life portfolios.
• Lead on strategic asset allocation decisions and adapt the portfolio structure to support both short- and long-term liability profiles.
• Evaluate macroeconomic trends, market conditions, and regulatory developments to inform investment decisions and capital deployment.

Outsourced Investment Oversight

• Own the day-to-day management of relationships with external investment managers across asset classes.
• Hold managers to account through robust performance analysis, risk-adjusted returns, fee transparency, and alignment with mandate objectives.
• Lead the manager selection and due diligence process when onboarding or reviewing investment partners.

Performance & Risk Monitoring

• Oversee investment performance reporting and attribution analysis across portfolios.
• Work with actuarial and finance teams to ensure portfolio risk and return remain well-aligned with insurance liabilities and solvency constraints.
• Engage in ongoing review of mandates to ensure efficiency, cost-effectiveness, and value for money.

Innovation & Value Creation

• Bring fresh, independent thinking to the table — identifying opportunities to enhance investment returns, diversify risk, or unlock capital efficiency.
• Explore new investment approaches (e.g., illiquids, ESG integration, liability-aware strategies) that align with our risk appetite and strategic goals.
• Build scenarios and proposals for "what we could be doing differently" — not just managing the current portfolio.

Governance & Stakeholder Engagement

• Support the CIO in preparing materials for the Board, Investment Committee, and regulators.
• Communicate investment strategy, rationale, and performance clearly to senior stakeholders, including non-investment experts.
• Ensure full regulatory compliance and adherence to internal governance frameworks.

Qualifications & Experience

• 10+ years of experience in investment management, ideally within or advising insurance companies (P&C and/or Life).
• CFA qualified or equivalent
• Strong knowledge of insurance-linked investment strategies, regulatory frameworks (e.g. Solvency II), and ALM principles.
• Proven experience working with outsourced managers: selection, oversight, performance analysis, and mandate structuring.
• Strong technical foundation in portfolio construction, fixed income, credit, and insurance-sensitive asset classes.
• Experience with strategic asset allocation modelling and scenario analysis.
• Excellent communication and stakeholder management skills.

What We Offer

• Opportunity to shape the investment strategy of a fast-growing specialist reinsurer.
• High visibility role reporting directly to the CIO and interacting with senior leadership.
• A flat and agile working environment with real autonomy.
• Competitive compensation, bonus, and benefits package.