Skyward Specialty Teams Up With Sixfold on AI Underwriting

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Skyward Specialty Insurance Group, Inc.TM (Nasdaq: SKWD) (“Skyward Specialty” or “the Company”), a leader in the specialty property and casualty (P&C) market, and Sixfold, an AI underwriting company transforming insurance workflows, announce a strategic partnership to accelerate the Company’s progress toward fully AI-powered underwriting across its U.S.-based property and casualty lines.

This collaboration reinforces Skyward Specialty’s long-standing commitment to a more data-driven, insight-rich and operationally efficient underwriting organization. Sixfold’s AI platform pre-processes submissions and generates data-driven recommendations, including prioritization, appetite alignment, and risk summarization and assessment, while keeping underwriters firmly in the loop to apply their judgment and expertise, ensuring high-quality outcomes.

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

“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.”

Sixfold’s platform is already live across six Skyward Specialty business units and more than 10 product lines, enabled by an average deployment timeline of 8 to 10 weeks. This level of speed-to-market is a testament to Sixfold’s technology and implementation discipline, and it reflects Skyward Specialty’s ability to rapidly 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.”