Episode #170
Dec 26, 2025
InsurTech 2025: A Year in Review & Predictions for 2026
With James Benham
and Rob Galbraith
SPONSORED BY
As 2025 wraps up, James Benham & Rob Galbraith reunite in a special episode of the InsurTech Geek Podcast to reflect on a transformative year in the insurance technology space. With AI moving from theory to production, cloud-native systems becoming the new standard, and user adoption still presenting real challenges, this episode offers deep insights into what defined the past year—and what to expect in 2026.
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The Shift from Pilots to Production
James and Rob both agreed—2025 marked a seismic shift. AI isn’t just a buzzword anymore; it’s a working, production-ready tool being deployed across underwriting, claims, and distribution.
“Now it’s full tilt implementation… it’s game time.” – James Benham
Insurance companies have gone from experimenting in “labs” to executing large-scale AI deployments. From record summarization to fraud detection to automated policy analysis, the industry is finally leveraging technology in ways previously thought too complex.
Cloud-Native & AI-Native: The New Baseline
In 2025, cloud-native and AI-native became more than marketing terms. They became minimum expectations.
James emphasized that for AI tools to function effectively—especially when integrated with platforms like Azure and OpenAI—the underlying infrastructure must support seamless access to structured and unstructured data in real time.
“If you’re not already cloud native, you’re going to struggle with AI.”
Organizations still relying on legacy systems are falling behind rapidly. Meanwhile, those who embraced scalable, agile cloud architectures are reaping the benefits of real-time automation and data analysis.
Engineers Still Matter—More Than Ever
Despite the rise of generative AI and agent-based automation, there’s no substitute for human expertise. AI can accelerate and automate—but it still requires engineers to guide and validate outputs.
“You still need talent driving the agents.” – James Benham
This theme echoed throughout the episode, reinforcing the need for upskilling and strategic hiring as AI adoption deepens.
User Adoption: The Final Mile
The biggest barrier? Human behavior.
Even the most sophisticated tools struggle to get traction if users don’t adopt them effectively. James shared that despite massive improvements in UX and functionality, convincing adjusters, underwriters, and frontline staff to trust AI remains a heavy lift.
“Getting people to actually use the tools is still the hardest part.”
Simple tweaks—like using heatmaps (via Microsoft Clarity) and reducing clicks—made a big difference. But user trust and change management remain core challenges.
2026 Predictions: Omnimodal Agents & New Contracts
Looking ahead, James predicts 2026 will be the year of the AI-powered agent—a single system that can perform multiple tasks across modalities: reading, writing, analyzing, predicting, even generating video.
“Omnimodal agents are coming—and they’re going to change everything.”
He also sees a shift in the way software is bought and sold. Expect shorter contracts, success-based pricing models, and more customer-friendly terms inspired by SaaS companies like HubSpot.
Challenges Ahead: Data, Ethics, and Retirements
Despite the progress, Rob warned that data quality issues, ethical considerations, and regulatory oversight remain hurdles. He highlighted the importance of ensuring human oversight, especially as AI tools begin making suggestions—or even decisions.
The pair also touched on an urgent issue: capturing tacit knowledge from retiring professionals before it disappears. AI systems must be trained now, while experienced adjusters and underwriters are still available.
Final Thoughts
This episode wasn’t just a recap—it was a blueprint for what’s coming. From practical deployments to big-picture strategy, it paints a clear picture of where the industry is headed.
“If you haven’t been to an InsurTech event, go. Meet people. Geek out.” – James Benham
Whether you’re in claims, IT, underwriting, or strategy, this conversation is a must-listen as we head into 2026.
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