Skyward Specialty Insurance Group (Skyward Specialty) and Sixfold, an artificial intelligence (AI) underwriting company, announce a strategic partnership to accelerate AI-powered underwriting across Skyward Specialty’s U.S.-based property and casualty (P&C) lines. The collaboration reinforces Skyward Specialty’s commitment to an operationally efficient underwriting organisation. The partnership, which is entering its second year, follows an initial pilot phase. Sixfold’s platform is currently live across six Skyward Specialty business units and more than 10 product lines, with an average deployment timeline of eight to 10 weeks. Sixfold’s AI platform pre-processes submissions and generates recommendations, including prioritisation, appetite alignment, and risk summarisation, while keeping underwriters involved to apply their expertise. Andrew Robinson, chairman and CEO of Skyward Specialty, says: “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”. Robinson adds: “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 centre of underwriting decisions. This is disciplined innovation that continues to position us for outperformance”. Alex Schmelkin, founder and CEO of Sixfold, comments: “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”. Skyward Specialty operates through nine underwriting divisions, including captives, professional lines, and surety. Its subsidiary insurance companies consist of Great Midwest Insurance Company, Houston Specialty Insurance Company, Imperium Insurance Company, and Oklahoma Specialty Insurance Company. These insurance companies are rated ‘A’ (Excellent) with a ‘stable’ outlook by AM Best.
