Slides
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2026 Analyst Day October 27, 2026
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Safe Harbor This presentation contains “forward-looking statements” within the meaning of the “safe harbor” provisions of the Private Securities Litigation Reform Act of 1995, including but not limited to, statements regarding our financial outlook, multi-year and long-term targets, strategic growth initiatives, and the proposed transaction with hyperexponential and expected benefits of the proposed transaction. These forward-looking statements are made as of the date they were first issued and were based on current expectations, estimates, forecasts and projections as well as the beliefs and assumptions of management. Words such as “expect, ” “anticipate, ” “should, ” “believe, ” “hope, ” “target, ” “project, ” “goals, ” “estimate, ” “potential, ” “predict, ” “may, ” “will, ” “might, ” “could, ” “intend, ” variations of these terms or the negative of these terms and similar expressions are intended to identify these forward-looking statements. Forward-looking statements are subject to a number of risks and uncertainties, many of which involve factors or circumstances that are beyond Guidewire’s control. Guidewire’s actual results could differ materially from those stated or implied in forward-looking statements due to a number of factors, including but not limited to, risks detailed in Guidewire’s most recent Forms 10-K and 10-Q filed with the Securities and Exchange Commission (“SEC”) as well as other documents that may be filed by the Company from time to time with the SEC. In particular, the following factors, among others, could cause results to differ materially from those expressed or implied by such forward-looking statements: risks related to the proposed transaction with hyperexponential, including unexpected costs, liabilities, or delays, the failure to consummate the transaction in a timely manner or at all, integration challenges, and risks related to incurring indebtedness to finance the transaction; our ability to execute on our multi-year goals and achieve our long-term operating frameworks and targets; fluctuations in our quarterly and annual operating results; our reliance on sales to, and renewals from, a relatively small number of large customers; the length and complexity of our sales, product development, and implementation cycles; our competitive environment and changes thereto; our ability to effectively manage international expansion; issues in the use of artificial intelligence (“AI”) and machine learning technologies combined with an uncertain and evolving regulatory environment; long-term pricing commitments and ramp structures in customer agreements; our ability to expand adoption of our cloud-based products and services, and the risk that any of our established products may fail to satisfy customer demands or maintain market acceptance; the impact of seasonal and other variations related to our customer agreements and revenue recognition on our results of operations, ARR, and cash flows; our ability to develop, introduce, and market new and enhanced versions of our products and services; our ability to retain existing and hire new personnel; errors or failures in our products or services, as well as service interruptions or failure of the third-party service providers we rely on; our dependence on the quality of our professional services and third-party global system integrator partners to sell our products and services; the impact of changes in our revenue mix, and the realization of lower gross margins from our services, subscription, and support revenues compared to our license revenue; the impact of global events; data security breaches of our cloud-based services and products or unauthorized access to our employees’ or our customers’ data; the impact of evolving regulations and laws; assertions by third parties that we violate their intellectual property rights; stock price volatility regardless of our operating performance; and other risks and uncertainties. The forward-looking statements included in this presentation represent Guidewire’s views as of the date of this presentation. The Company anticipates that subsequent events and developments will cause its views to change. Guidewire undertakes no intention or obligation to update or revise any forward-looking statements, whether as a result of new information, future events or otherwise. These forward-looking statements should not be relied upon as representing Guidewire’s views as of any date subsequent to the date of this presentation.
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Agenda 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
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Delivering on Intelligent Insurance Mike Rosenbaum Chief Executive Officer
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Guidewire: 25 years serving P&C insurance, a $3T industry by DWP Cloud Platform 550 Customers worldwide 44 Countries $1.6B FRARR 4,174 Employees $858B DWP Application Suite Pricing | Underwriting | Policy | Billing | Claims Marketplace & Ecosystem GUIDEWIRE AT A GLANCE (FY26) THE INTELLIGENT PLATFORM FOR P&C INSURANCE AI Agents • Data & Analytics • Digital Intelligent Insurance Serving 9 of top 10 worldwide insurers by DWP Over 330 successful cloud-based production core deployments worldwide 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. $390M Operating Cash Flow MISSION To power insurance agility with the platform insurers trust to engage, innovate, and grow efficiently
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AI impact on insurance ClaimsUnderwriting Platform and Data
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The insurance fundamentals driving Guidewire growth Core system sales (Claims, Policy, Billing, Pricing/Rating, Underwriting, Data & Analytics) ~$30B 1% of DWP Agentic Claims Agentic systems & traditional ML applied to Claims workflows ~$30B 1% of DWP Agentic Underwriting Agentic systems & traditional ML applied to Underwriting workflows ~$30B 1% of DWP Legacy tech decay & Security Consumer expectations Tech driven business agility Indemnity control Consumer experience expectations Operating efficiency Underwriting profitability Operating efficiency Competitiveness INSURANCE IMPERATIVE GUIDEWIRE GROWTH DRIVER ADDRESSABLE MARKET SIZE
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Guidewire + hx will transform commercial lines underwriting MARKET SHIFT Commercial lines underwriting will transform with AI AI improves industry ROE through three levers • Better understanding of pricing and risk • Less friction in distribution • Improved rate adequacy and portfolio analytics VALUE CREATION Agentic underwriting creates value across multiple layers From submission to bound policy • Risk Selection and Pricing • Submission ingestion • Triage and prioritization • Underwriting efficiency • Portfolio intelligence & profitability COMPETITIVE POSITION Guidewire + hyperexponential is best positioned to win Complementary strengths, one platform • Full coverage across underwriting, rating and policy admin • Covers commercial insurers needs worldwide • Adds world-class team of ~300
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Powering the complete insurance lifecycle Guidewire provides a suite of applications that cover the complete insurance lifecycle ClaimsPolicyUnderwritingDistributionPricingProduct
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Applications are delivered on an open, secure, AI enabled platform Marketplace Users + Agents Agents Platform Services Data Services Application Services Applications Agentic Framework Developers+Agents
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Customer success is powered by the leading P&C focused partner ecosystem Technology Partners >240 Partners >650 Available applications SI Partners >31K Professionals across 41 leading Systems Integrators Customers 550 Customers 44 Countries $858B DWP Consulting Partners Marketplace Solutions Developer Community 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.
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Driving Platform Expansion and Growth John Mullen President
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We serve a large and global market ~$3.0T DWP ~90 Insurers ~250 Insurers >2,000 Insurers ~$2.0T DWP ~$0.6T DWP ~$0.4T DWP Tier 1 DWP > $5B Tier 2 $1B < DWP < $5B Tier 3/4/5 DWP < $1B APAC AMER EMEA Tier 1 and 2 Insurers represent 85%+ of DWP supporting our sustained focus on the specific complexities of this segment Our ability to leverage a common platform worldwide allows us to more than double our AMER TAM Global industry with DWP across AMER/EMEA/APAC 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.
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We continue to achieve high win rates Undisclosed 14 Vendors Core System Decisions Core System Decisions by DWP 14 Vendors Guidewire (Cloud Upgrades) Guidewire 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. Undisclosed
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100% = $2.0T 100% = $0.6T 100% = $0.4T DWP Penetration by Tier Tier 1: >$5B DWP Tier 2: >$1B to <$5B DWP Tier 3/4/5: <$1B DWP Opportunity GWRE Cloud GWRE On-Premise Continuing durable capture of market across carrier size 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.
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DWP Penetration by Region Continuing to build for global expansion 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.
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The largest insurers are expanding on our platform as they seek a reliable core that enables agility, speed, and innovation 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. 3-year CAGR in Top 10 customers’ in-scope premium FY23 – FY26 21% 28% 3-year CAGR in Top 10 customers’ FRARR FY23 – FY26 30 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 %
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The Agentic future for Insurance meaningfully expands our TAM DWP Monetization DWP Penetration Agentic automation of claims and underwriting Analytics and data services Existing Contracted Customers’ DWP: $858B Expand DWP , cross-sell, upgrade to cloud +$4B Current FRARR: $1.6B Rest of market DWP: ~$2.1T New customer wins +$8B 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 Enterprise rating and pricing systems IT led Chief Information Officer Business led Chief Claims Officer, Chief Underwriting Officer, COO Insurance outcomes: premium growth, risk selection, profitability, Indemnity leakage, fraud, litigation avoidance, subrogation, operational leverage and scale
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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. Our partner ecosystem amplifies our platform potential Technology Partners >240 Partners >650 Available applications SI Partners >31K Professionals across 41 leading Systems Integrators Customers 550 Customers 44 Countries $858B DWP Consulting Partners Marketplace Solutions Developer Community
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Growth Focus - powering Agentic Carriers for the future Analytics Operational Insights Risk Decisions Portfolio Optimization Japan, Germany, France Country Content Program execution Regulatory aligned Migration and Modernizations Referenceability Strategic Roadmap Program Speed Segment and LOB Focus Commercial Lines All lines of business Work Comp Agentic Portfolio Expansion ProNavigator Agentic UW & Claims Agentic Framework Concierge
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Customer Perspective Daniel Wuest Senior Vice President, Products, Engineering & Architecture CNA Insurance Nitin Jain Vice President of Digital Transformation Donegal Insurance Group Christina Colby Chief Customer Officer Guidewire Paige Vincent Chief Operations Officer Hollard Insurance Australia
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Building on our Cloud Model Jeff Cooper Chief Financial Officer
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Key financial highlights Durable ARR and Fully Ramped ARR growth supported by cloud migration and modernization cycles Decades-long customer relationships with best-in-class retention Strong new product momentum Gross margin expansion continuing Continued execution driving profitable growth
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FY26: another year of strong execution Source: Guidewire Analysis. Note: ARR results are as of the FX rate at end of each respective fiscal year. FY27E is the midpoint of the outlook provided on our 9/3/26 earnings call and is organic (excludes hyperexponential). $ ARR in millions 14% 7-yr CAGR 19% 3-yr CAGR
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InsuranceSuite cloud customers: expansion continues to compound 37% 6-yr CAGR 46% 6-yr CAGR Total Cloud ARR InsuranceSuite Cloud Customer ARR $ in millions $ in millions Source: Guidewire Analysis. Note: Total Cloud ARR includes ARR from all cloud products. When on-premise customers upgrade to InsuranceSuite Cloud, the full cloud upgrade ARR is counted as Cloud ARR from the contract’s start date. InsuranceSuite Cloud Customer ARR includes the ARR of all products sold to InsuranceSuite Cloud Customers.
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Cohort economics: why ramps make growth predictable Source: Guidewire Analysis. Note: This analysis considers the incremental ARR fee schedule outlined in the relevant InsuranceSuite Cloud (ClaimCenter, PolicyCenter, BillingCenter) contracts, inclusive of contracted, but non-committed ramps. If the relevant fee schedule is less than five years, then this analysis assumes that final year fees will renew at the same value as the terminal year. For migration deals, this analysis specifically considers the incremental ARR above the existing on-prem ARR that existed prior to entering into a cloud migration arrangement. Cohort analysis is as of the point of sale and does not include non-core expansion orders, DWP true-ups or CPI adjustments that occur later.
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Durable ARR growth Source: Guidewire Analysis. Note: ARR results are as of the FX rate at end of each respective fiscal year. FY27E is the midpoint of the outlook provided on the previous earnings call and is organic (excludes hyperexponential).
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Updating FRARR definition: a clearer, simpler lens on growth • Adjusting our definition of FRARR to remove the 5 year limitation • New metric better aligns to our internal systems • As more deals now run longer than 5 years, the old 5-year rolling window wasn’t capturing years 6+ • FRARR reflects the full contracted fee schedule outlined in negotiated and executed customer contracts Shifting away from a year-5 rolling window to the final contracted fee FY24 FY25 FY26 FX as of: 7/31/23 7/31/24 7/31/25 FRARR, old $1065 $1285 $1578 FRARR, new $1077 $1305 $1611 Delta +$12 +$20 +$33 FRARR Growth, old 19% 22% 22% FRARR Growth, new 19% 22% 22% Source: Guidewire Analysis. Notes: All FRARR figures and growth rates are presented in in-year constant currency. “FRARR, old” uses previous methodology of a 5-year forward looking rolling window of contracted fees. For contracts shorter than 5 years in duration, the terminal year (last year) of the contract is assumed to renew at the same rate and is considered the FRARR. “FRARR, new” is the new methodology of using the terminal year fees of a contract regardless of duration. In the case where the committed term and the contracted term in a contract are not the same, the contracted term is used. For contracts with Termination For Convenience (TFC) clauses, if the TFC is less than one year, the ARR and FRARR is not recognized until the TFC period has expired. If the TFC is greater than one year, ARR is recognized upon the subscription start date and the terminal contracted term is recognized as FRARR upon signing.
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InsuranceSuite Cloud contracted ramps extend past year 5 Source: Guidewire Analysis. Note: This analysis considers the incremental ARR fee schedule outlined in the relevant InsuranceSuite Cloud contracts, inclusive of contracted, but non-committed ramps. This analysis assumes that final year fees will renew at the same value as the terminal year. For migration deals, this analysis specifically considers the incremental ARR above the existing on-prem ARR that existed prior to entering into a cloud migration arrangement. Cohort analysis is as of the point of sale and does not include non-core expansion orders, DWP true-ups or CPI adjustments that occur later.
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ARR backlog and visibility into FY27, through the contracted ARR lens Source: Guidewire Analysis. ARR from Backlog indicates incremental ARR from contracted ramp activities. FY27E estimates do not include the impact of hyperexponential. • Strong growth in ARR backlog expectation as a result of ramps • Year-over-year growth expected in Q1, Q2 and Q3 • FY27E returns to more normalized seasonality of ARR backlog Expected ARR backlog in Gross Dollars Expected ARR backlog per quarter as % of Total Backlog Q4 Q3 Q2 Q1
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Subscription and Support gross margin: the scale story continues • Margin expansion is driven by durable subscription revenue growth • Improving cost and operating efficiencies will continue to drive margin expansion Subscription and Support Gross Margin Headcount CostsOther Costs Subscription and Support Gross Margin/Profit ($ in millions) Source: Guidewire Analysis. Note: Non-GAAP subscription & support margins. Headcount Costs include compensation, benefits, employee welfare, travel, facilities, contractors, allocations and intercompany adjustments. Other Costs include cloud infrastructure, software and other non-headcount related expenses. FY27E reflects midpoint of guidance. FY27E estimates do not include the impact of hyperexponential. Subscription and Support Gross Profit
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Operating Cash Flow is hitting its stride Source: Guidewire SEC filings and Guidewire analysis. Note: FY27E reflects midpoint of guidance. FY27E estimate does not include the impact of hyperexponential. $ in millions
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Commentary on prior year FY28 goals (excludes hx impact) FY24A FY25A FY26A FY27E FY28E Midpoint Outlook Previously Stated FY28 Goals ARR Growth (constant currency) 14% 19% 19% 18% 17-18% (3-yr CAGR thru FY28) 18-19% (3-yr CAGR thru FY28) Cloud ARR % (constant currency) 66% 74% 84% 85%+ 90%+ ON TRACK Total Revenue Growth 8% 23% 23% 16% 15-16%* (3-yr CAGR thru FY28) ABOVE (3-yr CAGR thru FY28) Subs & Support Gross Margin 66% 70% 75% 75.5% 73-75% ABOVE Total Gross Margin 63% 66% 67% 67.5% 67-68% ABOVE Non-GAAP Operating Margin 10% 17% 23% 24% 25-28% ON TRACK Non-GAAP Operating Margin minus SBC (5%) 4% 11% 12% 14-17% ON TRACK Operating Cash Flow Margin 20% 25% 26% 26% 28-31% ON TRACK Note: FY27 midpoint outlook is from the outlook provided on our 9/3/26 earnings call. Gross margin numbers are non-GAAP . FY27E and FY28E estimates are organic and do not include impact of hyperexponential. * From previous Analyst Day 2025 footnote, goal for Total Revenue Growth (excluding Services Revenue) is 17-18% CAGR (FY25-FY28)
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Driving upper teens organic growth through $3B in ARR Migrations Modernizations New Products On-premise customers to migrate New core module expansion, new LOB expansion and net-new customers Evaluate inorganic opportunities PricingCenter UnderwritingCenter Industry Intel Unlock Agentic ProNavigator Agentic Claims / Underwriting Potential M&A
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Transaction overview: hyperexponential acquisition • Cash consideration of ~$1.7B, inclusive of employee retention pool, plus a contingent earnout of up to $400M payable based on post-close performance • Initial financing of $1.0B Term Loan A; remainder funded with cash on balance sheet • Term Loan A structure provides flexibility and Guidewire will evaluate the optimal long-term capital structure options • Closing expected in Q2 FY27 (Guidewire fiscal quarter ending January 31, 2027) • Closing is not subject to financing condition • Cash consideration of ~$1.7B, inclusive of employee retention pool, plus a contingent earnout of up to $400M payable based on post-close performance • Initial financing of $1.0B Term Loan A; remainder funded with cash on balance sheet • Term Loan A structure provides flexibility and Guidewire will evaluate the optimal long-term capital structure options Transaction details • Closing expected in Q2 FY27 (Guidewire fiscal quarter ending January 31, 2027) • Closing is not subject to financing condition Anticipated closing • Adds 650+ bps to expected FY27 ARR growth (inorganic) • Supports acceleration of organic ARR growth rate by at least 150 bps after FY27 • No impact to Q1 guidance; FY27 guidance will be updated on the Q1 earnings call Expected financial impact
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Achieve 80/40 plan by the time we get to $3B in ARR Subscription and support gross margin - Non-GAAP ~80% Operating Margin - Non-GAAP ~40% SBC as % of revenue Below 10% How Do We Get There? Strong incremental margins • Durable Cloud ARR growth • Scale benefits continue to positively impact gross margins • Resulting in healthy incremental margins Maintain OPEX discipline • OPEX spend growth slower than ARR growth • Prioritize R&D investments followed by targeted S&M investments This is a framework • Continue to recalibrate based on growth opportunities and other potential market conditions • Will prioritize growth over timeline to achieve the 80/40 plan Long-term Targets
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Reconciliation of non-GAAP gross margin and operating margin 2020 2021 2022* 2023 2024 2025 2026** 2027E GAAP Gross Margin 55% 52% 47% 51% 60% 63% 64% 65% Stock-based compensation 4% 5% 4% 4% 3% 3% 3% 3% Amortization of intangibles 3% 2% 1% 0% 0% 0% 0% 0% Non-GAAP Gross Margin 61% 59% 52% 55% 63% 66% 67% 68% GAAP Operating Margin (3%) (14%) (25%) (17%) (5%) 3% 10% 12% Stock-based compensation 14% 15% 17% 16% 15% 13% 12% 12% Amortization of intangibles 4% 3% 2% 2% 1% 0% 1% 0% Non-GAAP Operating Margin 14% 4% (6%) 1% 10% 17% 23% 24% Source: Guidewire Analysis. *Effective as of the beginning of fiscal year 2023, the Company revised its allocation methodology for determining the presentation of certain expenses. Accordingly, prior period amounts have been reclassified to conform to our current period presentation. **Certain FY26 figures included in this document have been subjected to rounding adjustments. Accordingly, figures shown in the same category presented in different tables may vary slightly and figures shown as totals in certain tables may not be an arithmetic aggregation of the figures that precede them. FY27E estimates are organic and do not include the impact of hyperexponential.
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2020 2021 2022* 2023 2024 2025 2026** 2027E GAAP Subscription & Support Gross Margin 42% 38% 41% 51% 63% 68% 73% 73.9% Non-GAAP adjustments: Stock-based compensation 4% 4% 4% 3% 3% 2% 1% 1% Amortization of intangibles 9% 4% 2% 1% 0% 0% 0% 0% Non-GAAP Subscription & Support Gross Margin 55% 46% 47% 55% 66% 70% 75% 75.5% Reconciliation of non-GAAP subscription and support gross margin Source: Guidewire Analysis. *Effective as of the beginning of fiscal year 2023, the Company revised its allocation methodology for determining the presentation of certain expenses. Accordingly, prior period amounts have been reclassified to conform to our current period presentation. **Certain FY26 figures included in this document have been subjected to rounding adjustments. Accordingly, figures shown in the same category presented in different tables may vary slightly and figures shown as totals in certain tables may not be an arithmetic aggregation of the figures that precede them. FY27E estimates are organic and do not include the impact of hyperexponential.
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Q&A