Skyward Specialty partners with Sixfold to advance AI underwriting

December 29, 2025

Skyward Specialty Insurance Group, a specialty property and casualty insurer focused on complex and niche risks, has partnered with Sixfold to accelerate its move towards AI-powered underwriting across its domestic P&C portfolio.

The partnership reflects Skyward Specialty’s ongoing efforts to enhance underwriting performance through data-driven insight, improved efficiency and faster decision-making.

Skyward Specialty underwrites across multiple specialty P&C lines, working closely with broker partners to deliver tailored insurance solutions.

Sixfold provides an AI underwriting platform designed to streamline insurance workflows. The technology pre-processes submissions and delivers structured recommendations such as risk summaries, appetite alignment and prioritisation.

Under the partnership, Sixfold’s platform has been rolled out across six Skyward Specialty business units and more than 10 product lines. Average deployment timelines of eight to ten weeks have allowed the insurer to rapidly scale the technology across its operations.

Andrew Robinson, Chairman and CEO of Skyward Specialty said, “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.

“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.”