Skyward Specialty Insurance Group announced a strategic partnership with AI underwriting firm Sixfold to accelerate the company’s transition to fully AI‑powered underwriting across its U.S. property and casualty lines.
Sixfold’s platform will pre‑process submissions, generate data‑driven recommendations, and automate routine tasks while keeping underwriters in control of final decisions. The technology is already live in six Skyward divisions and more than ten product lines, with an average deployment timeline of eight to ten weeks.
The partnership is a key element of Skyward’s “Rule Our Niche” strategy, which seeks to use technology to maintain high margins in specialty markets. By automating research and risk assessment, the company expects to increase the volume of submissions handled, improve pricing accuracy, and strengthen broker relationships—factors that support margin expansion and growth in commercial property and casualty business.
Andrew Robinson, Chairman and CEO, said the deal “elevates 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.” Alex Schmelkin, CEO of Sixfold, added that “Skyward underwriters use Sixfold daily, allowing them to enhance their expertise, reduce manual tasks and ensure consistency, giving Skyward a real competitive advantage.”
Skyward’s Q3 2025 results—net income of $45.9 million and gross written premiums of $606.5 million—demonstrate the company’s strong financial foundation and its capacity to invest in technology. The partnership follows a series of AI initiatives, including a previous collaboration with Gradient AI, and comes as the company prepares to close its acquisition of Apollo Group Holdings Limited in early 2026.
By integrating Sixfold’s AI tools, Skyward positions itself to capture additional market share in specialty lines, improve underwriting speed and consistency, and sustain high margins amid industry pressure. The partnership signals management’s confidence in technology as a driver of long‑term growth and competitive advantage.
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