Reinsurance News

Skyward Specialty to advance AI-powered underwriting with Sixfold partnership

23rd December 2025 - Author: Kassandra Jimenez-Sanchez -

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Skyward Specialty, a property and casualty insurer, has partnered with AI underwriting company Sixfold to accelerate the company’s progress toward fully AI-powered underwriting across its US-based P&C lines.

This collaboration reinforces Skyward Specialty’s long-standing commitment to becoming a more data-driven insight-rish and operationally efficient underwriting organisation.

Sixfold’s AI platform is designed to support underwriters by pre-processing submissions and offering data-driven recommendations, such as risk summarisation, appetite alignment, and prioritisation.

This ensures high-quality outcomes by enabling underwriters to apply their professional judgment with a comprehensive foundation of information.

Andrew Robinson, Chairman and CEO of Skyward Specialty, commented: “We are several years into our AI-powered underwriting journey. Our focus is about elevating our people – giving underwriters stronger insights, faster access to information and liberating their time to focus on making exceptional underwriting decisions and delivering top-notch service to our broker partners.

“Our partnership with Sixfold is another major step in this journey. The platform enhances underwriting insight, consistency, speed of analysis and response, and creates a virtuous learning loop that drives the best results while keeping human expertise at the center of underwriting decisions.”

Robinson added: “This is disciplined innovation that continues to position us for outperformance, and it forms a critical part of our learning curve and early mover advantage in the AI underwriting arms race. We are determined to maintain a leadership position in our use of advanced technology to serve the specialty insurance market, and our partnership with the team at Sixfold is a critical part of that ambition.”

Sixfold’s technology and implementation discipline have enabled rapid deployment across Skyward Specialty. Their platform is currently live in six business units and over ten product lines, with an average deployment time of just eight to ten weeks.

This speed-to-market highlight Skyward Specialty’s ability to quickly integrate high-impact innovation across the enterprise.

“After the initial pilot, Skyward’s first team went live in just ten weeks and immediately started scaling from there,” said Alex Schmelkin, Founder and CEO of Sixfold. “Skyward underwriters use Sixfold daily, allowing them to enhance their expertise, reduce manual tasks and ensure consistency, giving Skyward a real competitive advantage. This is what competing in 2026 looks like – and Skyward Specialty is already there.”