Head of Investment Operations

This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations.

Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose.  Our greatest strength is our talented colleagues, who flourish in a collaborative and entrepreneurial culture steeped in excellence, integrity, and a passion to find a better way., The Ascot Way.

The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our Client Centric, Risk Centric, and Technology Centric strategies.

Built to be resilient, Ascot offers clients leading financial security while delivering bespoke products and world class service — both pre- and post-claims. Ascot exists to solve our clients’ brightest tomorrow, through agility, collaboration, resilience, and discipline.

Ascot is embedding artificial intelligence (AI) and automation across the organization to enhance decision making, efficiency, and quality of outcomes. In this role, you will be expected to work confidently alongside AI-enabled tools, apply sound judgment when interpreting insights, and adapt as technology continues to evolve. We value curiosity, critical thinking, and a willingness to embrace change as part of how we work.

Position Overview:

Reporting to the Group Chief Investment Officer, the Head of Investment Operations will lead and continuously enhance the operating infrastructure that supports Ascot's global investment platform. The role will be responsible for building and scaling the Investment Function's operating model, including investment data management, reporting and analytics, technology enablement, operational governance, process design, and business infrastructure that support the organization's long-term growth objectives. The Head of Investment Operations will serve as a key architect of the Investment Function's operating model, ensuring that investment professionals are supported by scalable processes, high-quality data, modern technology platforms, and efficient workflows that improve transparency, productivity, and decision support. The role will partner closely with Investments, Investment Accounting, Finance, Treasury, Risk, and Technology to strengthen reporting accuracy, workflow efficiency, platform adoption, and operational controls. The successful candidate will bring deep insurance investment operations experience, strong analytical capability, and credibility across investment, finance, technology, and audit functions, with the ability to balance hands-on execution and day-to-day operational leadership while designing the scalable data, technology, reporting, and process infrastructure needed to support long-term portfolio growth.

Key Responsibilities:

• Reporting & Analytics: Lead recurring investment reporting, dashboard maintenance, financial analysis, and operational reporting activities across investment and business operations.
• Portfolio Operations: Oversee portfolio operations workflows, investment tracking, transaction-related processes, reconciliations, compliance, and operational controls to support accuracy, timeliness, and transparency.
• Data Management: Maintain, organize, and enhance financial, operational, and performance-related data to support reporting integrity, business insights, and leadership decision-making.
• Investment Platform Support: Support the ongoing development, maintenance, and adoption of proprietary investment operations and deal intelligence platforms.
• Cross-Functional Collaboration: Partner closely with investment, finance, technology, operations, and portfolio company teams to support reporting processes, investment tracking, platform enhancements, and operational initiatives.
• Process Improvement: Identify opportunities to improve workflows, strengthen controls, automate manual processes, and enhance reporting efficiency through AI-enabled tools, workflow automation, and operational technology.
• Testing & Documentation: Lead or support platform testing, workflow validation, user documentation, onboarding materials, training resources, and change management activities related to investment operations systems.
• Operational Leadership: Build and lead Ascot's investment operations function, defining the target operating model, standards, metrics, governance practices, and scalable infrastructure required to support long-term growth, while hiring and developing the team and balancing hands-on execution of day-to-day operations with the design of a modern, technology-enabled investment platform.

Requirements:

• Bachelor’s degree in Finance, Accounting, Business, Economics, or a related field is required.

• A minimum of 10 years of experience within investment operations at an insurer, reinsurer, institutional asset owner or asset manager is required, including at least three years leading an operations function or independently owning it end to end.
• Direct experience supporting insurance or reinsurance general account portfolios across multi-asset asset classes, including portfolio monitoring, performance reporting and operational support of the investment process, is required. Experience with private equity and other alternatives, including capital calls, illiquid valuations and GP reporting, is preferred.
• Prior insurance experience is strongly preferred. 
• Strong analytical skills, communication abilities, attention to detail, organizational skills, intellectual curiosity, and the ability to manage multiple priorities in a fast-paced environment are required.
• Demonstrated curiosity and practical experience using AI-enabled tools, automation, dashboards, or workflow technologies to improve reporting accuracy, operational efficiency, and business insights is preferred.
• Strategic and operational mindset with the ability to balance hands-on execution and long-term platform scalability.
• High degree of intellectual curiosity, judgment, and comfort working in an evolving, technology-enabled environment.
• Strong ownership orientation, accountability, and follow-through.
• Ability to operate with urgency, precision, and professionalism in a fast-paced environment.
• Collaborative leadership style aligned with The Ascot Way, including integrity, inclusion, entrepreneurial thinking, and a commitment to finding a better way.

**This role can be filled at a different level, depending on experience.**

Compensation:

Actual base pay could vary and may be above or below the listed range based on factors including but not limited to experience, subject matter expertise, and skills. The base pay is just one component of Ascot’s total compensation package for employees. Other rewards may include an annual cash bonus and other forms of discretionary compensation awarded by the Company. 

The annualized base pay range for this role is: $200,000 - $240,000 (Stamford, CT)

Company Benefits:

The Company provides a competitive benefits package that includes the following (eligibility requirements apply): 

• Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Life Insurance, AD&D, Work/Life Resources (including Employee Assistance Program), and more 
• Leave Benefits: Paid holidays, annual Paid Time Off (includes paid state /local paid leave where required), Short-term Disability, Long-term Disability, Other leaves (e.g., Bereavement, FMLA, Adoption, Maternity, Military, Primary & Non-Primary Caregiver) 
• Retirement Benefits: Contributory Savings Plan (401k)

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