Leah Rose
Chief Executive Officer
Leah was appointed as CEO in January 2026, having served as General Counsel and Claims Director for the past four years. During this time, she has played a central role in shaping the Syndicate’s strategic development within the Lloyd’s market. Leah is a practising solicitor, holds an ACII and has 20+ years’ legal and insurance experience. Leah brings continuity of leadership and a clear understanding of the Syndicate’s follow only model, culture and stakeholders.
Giancarlo D’Alessandro
Active Underwriter
Giancarlo was appointed as the syndicate’s Active Underwriter in January 2026, having joined the syndicate in July 2024 as Head of Portfolio Underwriting. He brings 15 years of (re)insurance experience, having managed and underwritten established Casualty portfolios at QBE Syndicates 386 and 1886, as well as AIG. Giancarlo holds an ACII and a first‑class bachelor’s degree.
Giancarlo has played a pivotal role in strengthening the syndicate’s underwriting capabilities, governance, and controls, while also spearheading its expansion into the company market.
Alice Gilbert
Underwriter
Alice began her career in 2014 on the Lloyd’s of London Apprenticeship scheme, where she gained a well-rounded experience of the London Insurance Market. In 2016, she joined Dale as an Underwriting Assistant on the North American Property Treaty Team and was promoted to Assistant Underwriter in 2020. Since joining HRP in 2023, Alice has been involved in HRP’s key short tail renewals, has developed its renewables strategy, and is involved in outwards reinsurance and exposure management. Alice holds an ACII.
Ben Ormerod
Chief Data Officer
Ben plays a key role in shaping HRP Syndicate 2689’s data strategy, leading the development of its management information capabilities and improving systems, processes and reporting across the business. He began his insurance career in 2009 at Ark Syndicates 4020/3902 before moving to Dale Syndicate 1729 as Business Intelligence and IT Manager. With extensive experience delivering data solutions and managing IT projects, he brings a strong understanding of the technical foundations required to support a modern, data-driven Lloyd’s syndicate.
