Rokstone, an international specialty re/insurance managing general agent (MGA), has announced the appointments of Robert Cheshire as Head of Pricing and Alastair Reed as Data Scientist within Rokstone Klik, its specialist US digital economy portfolio.
Cheshire joins the company from Chaucer, where he served as Treaty Pricing Actuary, bringing seven years of experience spanning actuarial pricing, portfolio management and innovation-led insurance.
His work within Chaucer’s innovation team gave him broad exposure to emerging technology, data-led underwriting and analytical approaches across multiple MGA platforms, adding significant depth to Klik’s pricing capability.
In his new position at Rokstone Klik, Cheshire will lead the creation of pricing frameworks tailored for intricate, high-volume, and data-intensive platform risks.
His role will include building technical pricing frameworks that combine actuarial discipline with real-time insight, analytics and emerging AI-enabled tools to support more accurate, forward-looking underwriting decisions.
Cheshire stated: “My ambition is to expand traditional approaches to insurance pricing and realise what is becoming possible with better data, better analytics and new technology.
“The opportunity at Rokstone Klik is to build pricing capability specifically for complex platform risks, where richer datasets make leading-edge modelling a reality. It is about blending grounded actuarial techniques with sharper tools to make pricing more informative, transparent and predictive.”
Reed brings specialist expertise in data science, quantitative modelling, statistical analysis and programming. A specialist in financial mathematics, and with expertise in data engineering and Python development, Reed will focus on translating complicated loss and exposure data into actionable intelligence.
Reporting to Andrew Cooper, Head of Rokstone Klik, Cheshire and Reed will help enhance Klik’s capacity to evaluate fast evolving US casualty risks that traditional markets struggle to price effectively, the firm stated.
Launched in 2026, Rokstone Klik was created to meet a gap in the US casualty market: the need for specialist underwriting of complex digital economy, mobility and platform risks, supported by modern pricing infrastructure
Cooper commented: “Robert and Alastair bring exactly the capabilities we want at Rokstone Klik. Robert combines deep pricing experience with a genuinely innovative mindset, while Alastair adds strong data science and quantitative expertise.
“Klik is being built for risks that do not always fit neatly into traditional underwriting models. Our strategy is to understand those businesses better, price them more intelligently and use technology to make faster, more predictive decisions. These appointments materially strengthen our ability to do that and to build a sophisticated, profitable portfolio at scale.”
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