2026 isn’t just a year for AI in underwriting. It’s the year.

As AI evolves at lightning speed, insurers are racing to stay ahead - not just to remain competitive, but to lead the next era of underwriting.

After years of pilots, proofs of concept, and cautious experimentation, this is the moment the industry separates promise from performance. We’ll see a clear divide between insurers who can turn AI’s potential into measurable business impact and those still stuck in experimentation. Early hype will finally give way to real, reliable results - and AI will shift from emerging technology to the system underwriting runs on.

We asked members of Kalepa’s leadership team to share their perspectives on what’s ahead for AI in underwriting and beyond. Their insights point to six major trends shaping 2026:

• AI Infrastructure Will Mature from Models to Systems
• AI Becomes a Growth Engine and Revenue Strategy
• AI Matures from Back-Office Tool to Competitive Advantage 
• Risk Intelligence Goes Deeper and Decisions Move Faster
• AI Narrows the Talent Gap 
• The Market Consolidates - and Winners Emerge 

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AI Infrastructure Will Mature from Models to Systems

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Paul Monasterio, CEO

“A critical challenge with AI - and especially with large language models - is that they’re non-deterministic. You can put the same inputs in and get different outputs,” 

“That unpredictability has made it difficult to fit AI into the traditional enterprise software model - particularly in highly regulated industries like insurance. It’s one reason so many pilots fail to move the needle.”

“In 2026, we’ll see an acceleration in how companies combine different types of AI and modeling approaches to make systems more effective, reliable, and explainable. This hybridization - combining deterministic and probabilistic methods, layering controls, and embedding human feedback loops - will be key to building trustworthy AI going forward.”

“At Kalepa, we’ve drawn lessons from fields outside of computer science - from medicine to mechanical and civil engineering - where systems are built to tolerate uncertainty and fail gracefully.The future of AI isn’t just about smarter models - it’s about smarter systems. Those who can build infrastructure that detects, corrects, and learns will be the ones who turn AI’s potential into production-grade reality.”

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Technology Becomes a Revenue Strategy 

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David Meister, Chief Revenue Officer  

“In 2026, we’ll see AI redefine what it means to compete in underwriting. The most successful insurers will use it to intelligently expand their risk appetite, accelerate quote turnaround, and unlock new revenue that would have been missed in the legacy model. These shifts will give insurers an unmatched ability to act with conviction and speed."

"We’ll see a clear separation between insurers who deploy modern underwriting systems at scale and those still exploring concepts in isolation. The former will grow, consolidate share, and outperform the market. The latter will struggle to keep pace in a landscape where AI isn’t an experiment anymore - it’s a requirement."

‍Christa Bicego, Director of Marketing

“In 2026, confidence in AI will become a competitive advantage in itself. We’ll see insurers not only using AI to drive efficiency and profitability - but also as a front-line differentiator."

“For the past few years, many insurers have been cautious, piloting quietly and waiting for proof. That’s going to shift. As systems mature and results have become measurable, the most forward-thinking insurers will start marketing their AI capabilities as proof points of speed, precision, and trust.”

“The industry narrative will evolve from ‘we’re experimenting with AI’ to ‘AI is how we underwrite.’ The insurers who communicate that confidently - backed by real results and transparency - will attract stronger broker relationships, better talent, and greater market trust.”

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Risk Intelligence Goes Deeper and Decisions Move Faster

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Piotr Czubak, VP Engineering

“In 2026, underwriting will be defined by the models that can see more, learn more, and act faster. Insurers will increasingly rely on AI to analyze far larger and more complex sources of data - from financial information and geospatial signals to satellite imagery and text-based documents. The result will be a level of risk insight that simply wasn’t possible before.”

“As models become more explainable and regulatory guidance matures, AI will support more transparent pricing and portfolio decisions. We’ll see underwriting retire fragmented and manual data gathering and fully shift to centralized intelligence that supports decision-making in real time.”

“One of the biggest shifts will be on the front end of the underwriting life cycle. Initial risk scoring will be nearly fully automated, allowing underwriters to immediately focus on exceptions, judgment-driven decisions, and the nuanced cases where expertise truly adds value.”

“In short, AI won’t just help underwriters work faster. It will fundamentally elevate how risks are assessed, priced, and managed - from the individual account to the entire portfolio.”

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Narrowing the Talent Gap

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Matthew Peck, VP Client Success

“One of the most overlooked shifts we’ll see in 2026 is how AI impacts talent. Underwriting has always been a craft developed over years - knowledge, intuition, and judgment are built gradually. But AI changes that learning curve.” 

“It narrows the gap between seasoned experts and newer underwriters by giving teams access to the same depth of insight, data, and decision support. The junior underwriters who embrace modern tooling will accelerate faster than we’ve ever seen before.”

“They’ll handle more complex risks earlier in their careers and contribute at levels that previously required far more time and experience. The organizations that invest in enablement and adoption will unlock that advantage sooner. This isn’t just about technology - it’s about the future of underwriting talent and how companies build their next generation of leaders.”

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The Market Consolidates - and Winners Emerge

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Marcin Kuczara, Director of Engineering

“2026 will be the year the insurance industry moves past experiments.  In previous years, we saw a wave of proof-of concepts driven by FOMO. The demand for AI was real, but the barrier to entry was low - it took only weeks for vendors to build something that looked like a solution."

"This dynamic changes significantly in 2026.  We now have established vendors driving consistent ROI.  The companies that struggled previously weren’t wrong about AI - they chose the wrong partners, the wrong architecture, or they cut corners."

"The market will begin to consolidate as a result.  POCs will disappear, bad vendors will fall away, and the leaders will establish a clear position.  Penetration of AI tools will increase, but the competitive landscape will tighten.”

“On the technology side, foundational models will improve in multimodality, predictability, and overall quality. We’ll see fewer hallucinations, more reliable outcomes, and better combinations of data, models, and infrastructure. Companies that can tie these together quickly and deploy them at scale will shape the future of the market.”

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The Bottom Line

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2026 marks the moment the industry moves from pilots to production. The winners will be the insurers who've built the infrastructure to make AI reliable, who've used it to grow revenue, and who've transformed AI capabilities into market differentiators that attract better broker relationships and top talent.

This is the year underwriting shifts from fragmented manual processes to centralized intelligence operating in real time. It's when junior underwriters equipped with modern tools accelerate past traditional learning curves, when initial risk scoring becomes nearly automatic, and when the market finally figures out which AI vendors deliver results and which ones are still figuring things out.

What used to be innovation work becomes everyday underwriting in 2026.