Analyst Day 2026 Final

TOPIC SPEAKER

Introduction Alex Hughes, Vice President, Investor Relations Delivering on Intelligent Insurance Mike Rosenbaum, Chief Executive Officer Driving Platform Expansion and Growth John Mullen, President

Customer Perspective Christina Colby, Chief Customer Officer

Building on our Cloud Model Jeff Cooper, Chief Financial Officer

Executive Q&A Executives

Cocktail Reception

Mike Rosenbaum

Chief Executive Officer

Guidewire: 25 years serving P&C insurance, a $3T industry by DWP

MISSION

To power insurance agility with the platform insurers trust to engage, innovate, and grow efficiently

Serving 9 of

top 10 worldwide insurers by DWP

Over 330 successful

cloud-based production core deployments worldwide

GUIDEWIRE AT A GLANCE (FY26)

Customers worldwide

Countries

FRARR

4,174

Employees

DWP

Operating Cash Flow

THE INTELLIGENT PLATFORM FOR P&C INSURANCE

Marketplace & Ecosystem

Note: Direct Written Premium (DWP) contracted to run on at least one of our core modules. FRARR is an acronym for Fully Ramped Annual Recurring Revenue.

Underwriting Claims

Platform and Data

MARKET SIZE

INSURANCE IMPERATIVE GUIDEWIRE GROWTH DRIVER ADDRESSABLE

Legacy tech decay & Security Consumer expectations

Tech driven business agility

Indemnity control

Consumer experience expectations Operating efficiency

Underwriting profitability Operating efficiency Competitiveness

Core system sales

(Claims, Policy, Billing, Pricing/Rating, Underwriting, Data & Analytics)

Agentic Claims

Agentic systems & traditional ML applied to Claims workflows

Agentic Underwriting

Agentic systems & traditional ML applied to Underwriting workflows

~$30B

1% of DWP

~$30B

1% of DWP

~$30B

1% of DWP

//*§ G UI D EWIRE

JF hypereHponential

Guidewire + hx will transform commercial lines underwriting

Product

Pricing

Distribution

Underwriting

Policy

Claims

Users + Agents Agents

Platform Services

Data Services

Application Services

Applications

Developers

+

Agents

Marketplace

Customer success is powered by the leading P&C focused partner ecosystem

Marketplace

Solutions

Consulting

Partners

Community

Developer

Customers

Customers

Countries

SI Partners

Professionals across

41 leading Systems Integrators

Technology Partners

DWP

Partners

Available applications

Note: Data as of July 31, 2026 except for SI Partners which is as of August 2026. As of July 31, 2026, we had approximately 550 customers in 44 countries. In some cases, our customers may represent more than one insurance brand. Our customer definition excludes customers that pay us less than

$10,000 per year, which primarily represents customers of our HazardHub product.

John Mullen

President

Sources: NAIC and "Swiss Re Institute, sigma 2/2026 World insurance in 2026 © Swiss Re. All rights reserved." US DWP from NAIC P&C insurance data. Non-US DWP from Swiss Re Sigma 2/2026 report, which estimates non-life premiums and is inclusive of A&H.

Core System Decisions Core System Decisions by DWP

14 Vendors

Guidewire

Undisclosed

14 Vendors

Undisclosed

Guidewire (Cloud Upgrades)

Source: Guidewire Analysis of core system decisions. "Undisclosed" includes internal build decisions or where selected vendor was unknown. Guidewire deals involving a cloud upgrade decision with a new core system decision are included in both Guidewire and Guidewire (Cloud Upgrades), but DWP associated with a migration and expansion decision is only counted once.

DWP Penetration by Tier

Tier 1: >$5B DWP Tier 2: >$1B to <$5B DWP Tier 3/4/5: <$1B DWP

100% = $2.0T 100% = $0.6T 100% = $0.4T

Opportunity GWRE Cloud GWRE On-Premise

Sources: Guidewire Analysis reflecting contracted DWP for one or more core modules. Industry analysis per NAIC and Swiss Re sigma 2/2026. US DWP from NAIC P&C insurance data. Non-US DWP from Swiss Re sigma 2/2026 report, which estimates non-life premiums and is inclusive of A&H.

DWP Penetration by Region

Core DWP - AMER Core DWP - EMEA Core DWP - APAC

100% = $1.3T 100% = $1.1T 100% = $0.6T

Opportunity GWRE Cloud GWRE On-Premise

Sources: Guidewire Analysis reflecting contracted DWP for one or more core modules. Industry analysis per NAIC and Swiss Re sigma 2/2026. US DWP from NAIC P&C insurance data. Non-US DWP from Swiss Re sigma 2/2026 report, which estimates non-life premiums and is inclusive of A&H.

21% 28% 30%

3-year CAGR in Top 10 customers' in-scope premium

FY23 - FY26

3-year CAGR in Top 10 customers' FRARR FY23 - FY26

3-year CAGR in count of customers over $5m FRARR

FY23 - FY26

13% 3-year CAGR for overall GWRE DWP

21% 3-year CAGR for overall GWRE FRARR

105 customers in FY26 vs 48 in FY23

Source: Guidewire Analysis. Top 10 customers determined by FRARR as of Q4'2026. In-scope DWP refers to total DWP under contract with a Guidewire core system, taking the largest DWP baseline if multiple baselines exist. FRARR in this analysis is under the previous definition of FRARR, using a forward-looking 5-year window of contracted annual fees. Customers over $5M are accounted for using FY23 and FY26 FX rates, respectively.

Analytics and data services

Enterprise rating and pricing systems

Insurance outcomes: premium growth, risk selection, profitability, Indemnity leakage, fraud, litigation avoidance, subrogation, operational leverage and scale

DWP Monetization

Business led

Chief Claims Officer, Chief Underwriting Officer, COO

Current FRARR: $1.6B

New customer wins +$8B

IT led

Chief Information Officer

Existing Contracted Customers' DWP: $858B

Rest of market DWP: ~$2.1T

DWP Penetration

Note: Guidewire Analysis. For illustrative purposes, not drawn to scale. FRARR is an acronym for Fully Ramped Annual Recurring Revenue. DWP Monetization represents ARR potential per dollar of DWP

Marketplace

Solutions

Consulting

Partners

Community

Developer

Customers

Customers

Countries

SI Partners

Professionals across

41 leading Systems Integrators

Technology Partners

DWP

Partners

Available applications

Note: Data as of July 31, 2026 except for SI Partners which is as of August 2026. As of July 31, 2026, we had approximately 550 customers in 44 countries. In some cases, our customers may represent more than one insurance brand. Our customer definition excludes customers that pay us less than

$10,000 per year, which primarily represents customers of our HazardHub product.

Referenceability Strategic Roadmap

Program Speed

Migration and Modernizations

Commercial Lines All lines of business

Work Comp

Segment and LOB Focus

ProNavigator Agentic UW & Claims Agentic Framework

Concierge

Agentic Portfolio Expansion

Country Content Program execution

Regulatory aligned

Japan, Germany, France

Operational Insights Risk Decisions

Portfolio Optimization

Analytics