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AI Briefing

Jul 1, 2026

Q2 ’26 AI Briefing: Why the Model Is No Longer the Advantage

Q2 ’26 AI Briefing: Why the Model Is No Longer the Advantage

Q2 showed that AI models will keep getting stronger, more accessible, and more tightly regulated, but the model itself is not where lasting advantage lives. For insurers, the real differentiator is the harness around it: the systems that connect AI to underwriting data, workflows, rules, and accountability.

Paul Monasterio

Q2 ’26 AI Briefing: Why the Model Is No Longer the Advantage

The Real AI Shift: A Redesigned Division of Labor

AI in underwriting

Paul Monasterio

The Real AI Shift: A Redesigned Division of Labor

AI in insurance is not just a story about faster processing or greater efficiency; it is a fundamental redesign of underwriting work. As AI takes on what slows underwriters down, human expertise concentrates where it actually moves the portfolio: risk selection, judgment, profitable growth.

Paul Monasterio

Before AI Can Follow Your Rules, You Have to Identify Them

AI in underwriting

Before AI Can Follow Your Rules, You Have to Identify Them

Conventional wisdom says fix your processes before deploying AI. But for most insurers, the deployment itself is the first time their underwriting logic gets tested against reality.

What Walks Out the Door When Underwriters Retire

AI in underwriting

What Walks Out the Door When Underwriters Retire

The insurance talent crisis is actually a judgment problem - and the expertise walking out the door is the kind that doesn't transfer through onboarding, training manuals, or guidelines documents.

Why Predicting Submission Value Starts with How Risks Relate

AI in underwriting

Why Predicting Submission Value Starts with How Risks Relate

Every carrier has data about what they write and where they compete. Few have a way to organize it into a framework that learns from every submission - not just the ones they quoted.

When AI Meets Complexity, Architecture Decides

Paul Monasterio

When AI Meets Complexity, Architecture Decides

AI models are more capable than they were months ago - so why do most enterprise deployments still struggle to deliver? It's not the models, it's what surrounds them. And other fields figured this out a long time ago.

Paul Monasterio

Navigating Soft Markets: 4 Levers That Separate Winners from Survivors

AI in underwriting

Paul Monasterio

Navigating Soft Markets: 4 Levers That Separate Winners from Survivors

Soft markets test whether underwriting discipline is real or just rhetoric. These four operational levers help insurers maintain precision, protect the portfolio, and position for the next cycle.

Paul Monasterio

AI That Reasons: What It Means For Insurance

AI in underwriting

AI That Reasons: What It Means For Insurance

When an AI model can check its own logic before producing an answer, every underwriting task becomes more reliable - from classification to exposure detection. Here's what changed, and why the model is only part of the story.

AI Has Stopped Being a Capability Question

Paul Monasterio

AI Has Stopped Being a Capability Question

Model releases, regulatory shifts, autonomous agents, and a Pentagon contract collapse. Q1 2026 reshaped the AI landscape. Here's what each story means for how insurers will compete over the next two to three years.

Paul Monasterio

What Medicine Teaches Us About Building Professional Grade AI

AI in underwriting

February 24, 2026

What Medicine Teaches Us About Building Professional Grade AI

How Kalepa takes inspiration from medicine - a field built to operate safely amid variability - and what that means for AI in insurance.

Building Trust in AI: Coupling Extraction and Judging Agents for Insurance Submission Processing

AI in underwriting

February 4, 2026

Building Trust in AI: Coupling Extraction and Judging Agents for Insurance Submission Processing

Kalepa delivers market-leading underwriting accuracy by extracting structured data from diverse submission documents and validating critical fields with independent AI judging agents. This coupled approach continuously measures confidence, catches subtle errors, and sustains consistent quality at scale.

2026 Predictions for AI in Underwriting

AI in underwriting

2026 Predictions for AI in Underwriting

Members of Kalepa’s leadership team break down the six trends that will define the year - from maturing AI infrastructure to faster decisions, a narrowing talent gap, and a tighter competitive landscape.

2025: The Rise of Professional-Grade AI in Insurance

AI in underwriting

Paul Monasterio

2025: The Rise of Professional-Grade AI in Insurance

In 2025, insurance moved past AI hype and into the Professional-Grade AI era, where trustworthy, production-ready systems deliver real underwriting impact - and Kalepa is leading the way.

Paul Monasterio

The Next Phase of Underwriting Intelligence - Agentic AI

AI in underwriting

Paul Monasterio

December 30, 2025

The Next Phase of Underwriting Intelligence - Agentic AI

Leading insurers have shifted from a focus on automating to a focus on delegating - to AI Agents.

Paul Monasterio

Three Questions with Ada Adamczak, Manager of Full Stack Engineering

Company & leadership

Three Questions with Ada Adamczak, Manager of Full Stack Engineering

Ada gives guidance to potential applicants, covers how our full stack team impacts Kalepa's clients, and shares how Kalepa's culture helps deliver results

2024: The Year of the Copilot

AI in underwriting

Paul Monasterio

2024: The Year of the Copilot

This was the year that Copilots finally went mainstream, setting up a tremendous year for us at Kalepa.

Paul Monasterio

Three Questions with Vahini Patel, Manager - Customer Success

Company & leadership

Three Questions with Vahini Patel, Manager - Customer Success

Vahini offers her perspective on why she joined Kalepa, how our customer success team helps insurers hit their growth and profitability targets, and why Kalepa's focus on hustle and transparency creates a culture of getting stuff done

The No-Code Mirage: The Hidden Costs of No-Code Builds for Insurers

Underwriting Operations

Paul Monasterio

The No-Code Mirage: The Hidden Costs of No-Code Builds for Insurers

No-Code solutions are often viewed as a middle path in the Build vs. Buy debate. But a No-Code Build is still a Build - just with extra downsides

Paul Monasterio

Three Big AI Buzzwords Insurers Need to Know in 2025

AI in underwriting

Paul Monasterio

Three Big AI Buzzwords Insurers Need to Know in 2025

AI Agents, Explainable AI, and new foundational models are some of the biggest topics in AI right now. Here’s why they matter for insurers.

Paul Monasterio

That Worked: Episode 61 with Paul Monasterio

Company & leadership

That Worked: Episode 61 with Paul Monasterio

Kalepa CEO Paul Monasterio joins host Callan Harrington to discuss transparency, finding the ideal co-founder, and partnering with Kalepa's early customers

2023: Predictably Unpredictable

AI in underwriting

Paul Monasterio

2023: Predictably Unpredictable

I continue to observe two secular trends that intersected with many of the critical events of the year: the entirely predictable “unpredictability” as the world only continues to grow incomplexity as well as the rapid rise and evolution of technology in general and AI in particular.

Paul Monasterio

Paul Monasterio on the Insurtech Leadership Podcast

Underwriting Operations

Paul Monasterio on the Insurtech Leadership Podcast

Kalepa CEO Paul Monasterio joined host Joshua Hollander to discuss how Kalepa's Copilot underwriting workbench is empowering underwriters to bind faster and better than ever.

The PFAS Predicament: How Underwriters Can Respond

Underwriting Operations

Paul Monasterio

The PFAS Predicament: How Underwriters Can Respond

Many are worried that PFAS could be 'the next asbestos.' What is it, what can insurers do about it, and how can Copilot help them right away?

Paul Monasterio

The AI technique that no one in insurance is talking about

AI in underwriting

Paul Monasterio

The AI technique that no one in insurance is talking about

Summarizing articles, legal filings, and more for underwriters using the latest AI innovation

Paul Monasterio

Category Visionaries: Interview with CEO Paul Monasterio

Company & leadership

Category Visionaries: Interview with CEO Paul Monasterio

In this episode of Category Visionaries, Paul Monasterio, CEO and Co-Founder of Kalepa, joined host Brett Stapper for a wide ranging discussion on Paul's background, founding a successful startup, transforming the commercial insurance industry, and more.

Profiles in Risk Podcast - The Future of Underwriting

Underwriting Operations

Profiles in Risk Podcast - The Future of Underwriting

Listen to Tony Cañas and Paul Monasterio discuss innovation in commercial insurance, the future of underwriting, and how Kalepa's Copilot enhances underwriting and drives profitable premium growth on Tony's Profiles in Risk podcast.

The Leadership in Insurance Podcast - Enabling Insurers to Bind with Confidence

Company & leadership

The Leadership in Insurance Podcast - Enabling Insurers to Bind with Confidence

Listen to Alex Bond of FinPro. and Paul Monasterio of Kalepa discuss hype vs. reality in generative AI, augmentation vs. automation, and how insurers can best set up for success in the AI age.

From Buzzword Bingo to Business Success: How Insurers Can Navigate the AI Hype

AI in underwriting

Paul Monasterio

From Buzzword Bingo to Business Success: How Insurers Can Navigate the AI Hype

AI hype is at its highest point, but how can insurers separate the substance from the hype when it comes to new technologies? The answer is surprisingly simple.

Paul Monasterio

From Risk to Reward: The Impact of ChatGPT and LLMs on Underwriting

AI in underwriting

Paul Monasterio

From Risk to Reward: The Impact of ChatGPT and LLMs on Underwriting

Insurers are trying to figure out how to leverage the newest advances in AI, so we compiled the go-to guide.

Paul Monasterio

Underwriting technology is the solution to rising reinsurance rates — here’s why

AI in underwriting

Paul Monasterio

Underwriting technology is the solution to rising reinsurance rates — here’s why

What's driving them, and how can strong underwriting help insurers take back control?

Paul Monasterio

A Look Back at 2022: Permacrisis, AI, and Insurtech 2.0

AI in underwriting

Paul Monasterio

A Look Back at 2022: Permacrisis, AI, and Insurtech 2.0

Reflecting on a year of challenges and progress for the industry, and how Kalepa has responded

Paul Monasterio

Top 3 Things You Missed at Underwriting Innovation USA

Company & leadership

Top 3 Things You Missed at Underwriting Innovation USA

Didn't make it to the conference? Don't worry - we've got you covered.

Taking Kalepa to New Heights

Product updates

Paul Monasterio

Taking Kalepa to New Heights

Big changes are headed to Kalepa - get ready for an even smoother underwriting workflow.

Paul Monasterio

The Art of Winning Commercial Insurance: Lessons from Moneyball

Underwriting Operations

The Art of Winning Commercial Insurance: Lessons from Moneyball

Winning the insurance technology arms race requires a new strategy - and it's not what you think

Reflecting on 2021: Our Journey Towards the Efficient Frontier

Company & leadership

Paul Monasterio

Reflecting on 2021: Our Journey Towards the Efficient Frontier

CEO Paul Monasterio highlights the top industry changes and Kalepa's major milestones from the past year

Paul Monasterio

Why strong underwriting is insurance’s ‘alpha’

AI in underwriting

Paul Monasterio

Why strong underwriting is insurance’s ‘alpha’

If insurers want to outperform their competitors, high quality underwriting is the secret - here's why.

Paul Monasterio

Taking stock of 2020: Underwriting in an Ever-Changing World

Company & leadership

Paul Monasterio

Taking stock of 2020: Underwriting in an Ever-Changing World

At the end of a turbulent year across the globe, CEO Paul Monasterio reflects on Kalepa's ongoing growth and how we help insurers during this challenging time.

Paul Monasterio

The Insurance Industry’s Data Blind Spot—And How to Fix It

Underwriting Operations

The Insurance Industry’s Data Blind Spot—And How to Fix It

Messy, inconsistent data is one of the biggest obstacles to data-powered underwriting, and entity resolution is the issue insurers can’t afford to overlook.

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