Skyward Specialty and Sixfold Partner to Advance AI-Powered Underwriting

Rhea-AI Summary

Skyward Specialty (Nasdaq: SKWD) and AI underwriting provider Sixfold announced a strategic partnership on December 18, 2025 to accelerate Skyward Specialty's move toward fully AI-powered underwriting across its U.S. property and casualty lines. Sixfold’s platform pre-processes submissions and delivers recommendations for prioritization, appetite alignment, and risk summarization while keeping underwriters involved.

The platform is live across six Skyward business units and more than 10 product lines, with average deployments of 8–10 weeks and daily use by underwriters, which the companies say boosts consistency, speed of analysis, and operational efficiency.

Positive

• Live deployment across six business units
• Coverage across more than 10 product lines
• Average deployment timeline of 8–10 weeks
• Daily underwriter use reported, improving consistency and speed

Negative

• None.

News Market Reaction

+4.33%

1 alert

+4.33% News Effect

On the day this news was published, SKWD gained 4.33%, reflecting a moderate positive market reaction.

Data tracked by StockTitan Argus on the day of publication.

Key Figures

Business units live: 6 business units Product lines covered: more than 10 product lines Deployment timeline: 8 to 10 weeks +2 more

5 metrics

Business units live 6 business units Sixfold platform deployment across Skyward Specialty

Product lines covered more than 10 product lines AI underwriting platform rollout scope

Deployment timeline 8 to 10 weeks Average deployment time for Sixfold platform

First team go‑live 10 weeks Time from initial pilot to first team going live

Competitive timeframe 2026 Year referenced for competitive positioning in AI underwriting

Market Reality Check

Price: $44.89 Vol: Volume 276,803 is at 0.72...

normal vol

$44.89 Last Close

Volume Volume 276,803 is at 0.72x the 20-day average of 383,678, indicating subdued trading ahead of this AI partnership news. normal

Technical Shares at $49.65 are trading below the 200-day MA of $51.73 and about 23.67% under the 52-week high of $65.05.

Peers on Argus

While SKWD was up 1.1%, several peers also rose (e.g., TRUP +4.24%, HMN +1.57%, ...

While SKWD was up 1.1%, several peers also rose (e.g., TRUP +4.24%, HMN +1.57%, BOW +1.48%), but ROOT declined 4.32%, and no peers appeared in the momentum scanner, suggesting a more company-specific backdrop.

Historical Context

5 past events · Latest: Dec 03 (Positive)

Pattern 5 events

Date	Event	Sentiment	Move	Catalyst
Dec 03	Acquisition approval & guidance	Positive	-3.0%	Regulatory and minority approvals for Apollo deal plus detailed 2026 pro forma guidance.
Nov 19	Management promotion	Positive	-1.1%	Promotion of John Burkhart to President, U.S. Property & Casualty with expanded oversight.
Nov 11	Board appointment	Positive	+0.7%	Appointment of Christopher Peirce to the Board with planned Audit Committee leadership.
Oct 29	Earnings release	Positive	-0.3%	Q3 2025 results with higher net income, strong premium growth and sub-90% combined ratio.
Oct 13	Earnings call notice	Neutral	+0.4%	Scheduling and access details for the Q3 2025 earnings release and conference call.

Pattern Detected

Recent news often drew modest reactions, with several positive corporate updates followed by slight price declines, indicating mixed alignment between news tone and short-term moves.

Recent Company History

Over the past few months, Skyward Specialty reported strong financial and strategic progress. Q3 2025 results showed net income of $45.9M and gross written premiums of $606.5M, with a combined ratio of 89.2%. The company agreed to acquire Apollo, targeting Q1 2026 closing, and later secured regulatory and minority shareholder approvals while issuing 2026 guidance, including gross written premiums of $2.65B–$2.8B and net income of $207M–$216M. Leadership changes, including a new President of U.S. Property & Casualty and an incoming Audit Committee Chair, framed ongoing expansion and governance updates around this AI-focused announcement.

Market Pulse Summary

This announcement highlights Skyward Specialty’s continued investment in AI-enabled underwriting, ex...

Analysis

This announcement highlights Skyward Specialty’s continued investment in AI-enabled underwriting, extending a partnership with Sixfold that already spans six business units and more than 10 product lines, with deployment timelines of 8–10 weeks. In the context of recent strong earnings, the Apollo acquisition, and governance changes, the news underscores a strategy focused on data-driven underwriting and operational efficiency. Investors may watch adoption across additional lines and how these tools influence underwriting consistency, speed, and long-term profitability metrics.

Key Terms

ai-powered underwriting, risk summarization, underwriters

3 terms

ai-powered underwriting technical

"accelerate the Company’s progress toward fully AI-powered underwriting across its U.S.-based"

A process that uses machine learning and data analysis to automate and improve underwriting decisions—assessing risk, pricing, and approval for loans, insurance or securities—by spotting patterns across large datasets that a human reviewer might miss. For investors it matters because it can speed decisions, cut costs and improve pricing accuracy like a highly trained assistant scanning thousands of files, but it also introduces model risk, reliance on data quality and possible regulatory scrutiny.

risk summarization technical

"appetite alignment, and risk summarization and assessment, while keeping underwriters"

A concise summary of the main risks tied to an investment, product or business activity that highlights what could go wrong, how likely it is, and the potential impact. Think of it as a clear safety checklist or weather forecast for money: it helps investors quickly spot red flags, compare alternatives, and judge whether the potential reward justifies the chance of loss. Effective risk summarization makes complex dangers easier to weigh in decision-making.

underwriters financial

"keeping underwriters firmly in the loop to apply their judgment and expertise"

Underwriters are financial professionals or institutions that help companies raise money by selling new securities, such as stocks or bonds, to investors. They assess the risk and determine the price at which these securities should be sold, acting like a bridge between the company and the investors. Their role helps ensure that the company raises the needed funds while providing investors with options that reflect the level of risk involved.

AI-generated analysis. Not financial advice.

HOUSTON, Dec. 18, 2025 (GLOBE NEWSWIRE) -- Skyward Specialty Insurance Group, Inc.™ (Nasdaq: SKWD) ("Skyward Specialty" or "the Company"), a leader in the specialty property and casualty (P&C) market, and Sixfold (“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, which is entering its second year, is another important 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.”

About Sixfold
Sixfold is the AI brain that keeps underwriting in motion for leading P&C and L&H insurers. Built for underwriting from day one, the platform combines appetite-aligned insights with autonomous agents that clear bottlenecks and handle admin work. Underwriters process more submissions, generate higher GWP, and focus on judgment calls and broker relationships.

Learn more: www.sixfold.ai   

About Skyward Specialty
Skyward Specialty (Nasdaq: SKWD) is a rapidly growing and innovative specialty insurance company, delivering commercial property and casualty products and solutions on a non-admitted and admitted basis. The Company operates through nine underwriting divisions – Accident & Health, Agriculture and Credit (Re)insurance, Captives, Industry Solutions, Global Property, Professional Lines, Specialty Programs, Surety and Transactional E&S.

Skyward Specialty's 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 A.M. Best Company. For more information about Skyward Specialty, its people, and its products, please visit skywardinsurance.com.

Sixfold
Simon Hayes, M.D. (Media Contact)
NextGen Communications

E: simon@nextgencomms.com

Skyward Specialty Insurance
Haley Doughty (Media Contact)
713-935-4944
jmendez@skywardinsurance.com

Kevin Reed (Investor Contact)
713-206-7860 
kreed@skywardinsurance.com  

FAQ

What did Skyward Specialty (SKWD) announce on December 18, 2025 about AI underwriting?

Skyward Specialty announced a strategic partnership with Sixfold to expand AI-powered underwriting across its U.S. property and casualty lines.

How many Skyward business units use Sixfold's platform as of December 2025?

Sixfold’s platform is live across six Skyward business units.

Which Skyward product lines are using Sixfold's AI platform and how many?

The platform is enabled across more than 10 product lines at Skyward Specialty.

What is the typical deployment timeline for Sixfold at Skyward Specialty?

Average deployment timelines are reported at 8 to 10 weeks.

How does Sixfold's platform affect Skyward underwriters' workflow?

Sixfold pre-processes submissions and provides recommendations for prioritization, appetite alignment, and risk summarization while keeping underwriters in the loop.

Does Skyward Specialty claim the Sixfold partnership improves competitiveness for SKWD?

Skyward says the partnership enhances underwriting insight, speed, and consistency, supporting its position as an early mover in AI underwriting.