Exhibit 99.2 + Guidewire announces agreement to acquire hyperexponential October 27, 2026

Safe Harbor This presentation includes “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 the proposed transaction with hyperexponential (the “proposed transaction”), the expected timing of the closing of the proposed transaction, the ability of the parties to complete the proposed transaction, the expected benefits of the proposed transaction, the expected impact to Guidewire’s ARR growth for fiscal year 2027, and any assumptions underlying any of the foregoing. 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 represent Guidewire’s current expectations regarding future events and are subject to known and unknown risks and uncertainties that could cause actual results to differ materially from those implied by the forward-looking statements. Among those risks and uncertainties are the risk that the proposed transaction may not be completed in a timely manner or at all; the potential failure to receive, on a timely basis or otherwise, the required funding for the proposed transaction; the potential failure to consummate the proposed transaction; that the proposed transaction may involve unexpected costs, liabilities, or delays; and risks relating to Guidewire’s business, including those described in Guidewire’s most recent Forms 10-K and 10-Q filed with the Securities and Exchange Commission (the “SEC”) as well as other documents that may be filed by Guidewire from time to time with the SEC. Guidewire may not consummate the proposed transaction described in this presentation and, if the proposed transaction is consummated, cannot provide any assurances regarding the expected benefits of the transaction. The forward-looking statements included in this presentation speak only as of the date of this presentation, and Guidewire does not undertake to update the statements included in this presentation for subsequent developments, except as may be required by law.

Guidewire + hyperexponential WHO IS HX Guidewire brings hx brings System of record and transaction backbone Decision infrastructure for underwriting work hyperexponential (hx) is an agentic pricing and underwriting Policy administration Underwriting workflows platform for commercial and specialty insurance. Insurers, Billing and claims systems Pricing and rating engine reinsurers, and MGAs, from Lloyd’s to US commercial lines, Pricing and rating solutions Underwriting decisioning use hx to build pricing models, assess complex risk, Insurance data and hyperoperator and and optimize their portfolios. workflow infrastructure agentic automation Expanded portfolio and Scaled P&C customer base European and London Market reach WHY IT MATTERS This combination will accelerate Complementary strengths across commercial risk Better together the insurance industry's transformation to Agentic Combining Guidewire’s core systems and customer reach with hx’s pricing and underwriting expertise creates a complete insurance life cycle for commercial lines insurance. Underwriting by delivering the agentic technology platform Select the Steer the Price with Act at scale with to support every commercial right risks portfolio precision confidence line segment and risk.

Agentic Underwriting creates a large growth opportunity for Guidewire ADDRESSABLE INSURANCE IMPERATIVE GUIDEWIRE GROWTH DRIVER MARKET SIZE Legacy tech decay & Security Core system sales ~$30B Consumer expectations (Claims, Policy, Billing, Pricing/Rating, 1% of DWP Tech driven business agility Underwriting, Data & Analytics) Indemnity control Agentic Claims ~$30B Consumer experience expectations Agentic systems & traditional ML 1% of DWP Operating efficiency applied to Claims workflows Underwriting profitability Agentic Underwriting ~$30B Operating efficiency Agentic systems & traditional ML 1% of DWP Competitiveness applied to Underwriting workflows

Guidewire + hx will transform commercial lines underwriting MARKET SHIFT VALUE CREATION COMPETITIVE POSITION Commercial lines Agentic underwriting Guidewire + underwriting will creates value across hyperexponential is best transform with AI multiple layers positioned to win AI improves industry ROE through three levers From submission to bound policy Complementary strengths, one platform • Full coverage across underwriting, • Better understanding • Risk Selection and Pricing rating and policy admin of pricing and risk • Submission ingestion • Covers commercial insurers needs • Less friction in distribution • Triage and prioritization worldwide • Improved rate adequacy • Underwriting efficiency • Adds world-class team of ~300 and portfolio analytics • Portfolio intelligence & profitability

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 Transaction details Anticipated closing Expected financial impact • Initial financing of $1.0B Term Loan A; remainder funded with cash on balance sheet Transaction details • Term Loan A structure provides flexibility and Guidewire will evaluate the optimal long-term • Cash consideration of ~$1.7B, • Closing expected in Q2 FY27 • Adds 650+ bps to expected capital structure options inclusive of employee retention (Guidewire fiscal quarter ending FY27 ARR growth (inorganic) pool, plus a contingent earnout January 31, 2027) • Supports acceleration of of up to $400M payable based • Closing is not subject to organic ARR growth rate by on post-close performance • Closing expected in Q2 FY27 (Guidewire fiscal quarter ending January 31, 2027) financing condition at least 150 bps after FY27 Anticipated closing • Initial financing of $1.0B Term • Closing is not subject to financing condition • No impact to Q1 guidance; Loan A; remainder funded FY27 guidance will be updated with cash on balance sheet on the Q1 earnings call • Term Loan A structure provides flexibility and Guidewire will • Adds 650+ bps to expected FY27 ARR growth (inorganic) evaluate the optimal long-term Expected financial • Supports acceleration of organic ARR growth rate by over 100 bps after FY27 capital structure options impact • No impact to Q1 guidance; FY27 guidance will be updated on the Q1 earnings call