Exhibit 99.2

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

On November 1, 2017 (the “Cyence Acquisition Date”), pursuant to the Agreement and Plan of Reorganization entered into on October 5, 2017, Guidewire Software, Inc., a Delaware corporation (hereinafter referred to as “Guidewire”, “the Company”, “we”, “our”, “us” and similar terms unless the context indicates otherwise) completed its acquisition of Cyence, Inc., a Delaware corporation (“Cyence”). Additionally, on February 16, 2017 (the “ISCS Acquisition Date”), pursuant to the Agreement and Plan of Merger entered into on December 18, 2016, Guidewire completed its acquisition of ISCS, Inc., a California Subchapter S Corporation (“ISCS”). We collectively refer to Guidewire’s acquisition of Cyence together with the acquisition of ISCS, as the “Acquisitions”. The following unaudited pro forma condensed combined financial information presents the historical condensed combined financial statements of Guidewire, Cyence and ISCS after giving effect to the Acquisitions based on the assumptions, reclassifications and adjustments described in the accompanying notes to the unaudited pro forma condensed combined financial information.

The unaudited pro forma condensed combined statements of operations for the year ended July 31, 2017 is presented as if the Acquisition occurred on August 1, 2016, the first day of our 2017 fiscal year. The unaudited pro forma condensed combined statements of operations for the six months ended January 31, 2018 is presented as if the Acquisition occurred on August 1, 2016, the first day of our 2017 fiscal year. The Acquisitions have already been reflected in our historical unaudited condensed consolidated balance sheet as of January 31, 2018; therefore, no unaudited pro forma condensed combined balance sheet as of January 31, 2018 has been presented herein.

The unaudited pro forma condensed combined financial information was prepared in accordance with Article 11 of SEC Regulation S-X. The unaudited pro forma adjustments reflecting the Acquisitions have been prepared in accordance with business combination accounting guidance as provided in FASB Accounting Standards Codification 805, Business Combinations, and reflect the allocation of the purchase price of each acquisition to the acquired assets and assumed liabilities based on a estimates of fair values, using available information and the assumptions set forth in the notes to the unaudited pro forma condensed combined financial information. The purchase price allocation for the assets acquired and liabilities assumed in the Acquisitions is preliminary and may change in future reporting periods upon finalization of the valuation.

The unaudited pro forma condensed combined financial information for the year ended July 31, 2017 included herein was derived from our audited historical consolidated financial statements and the unaudited pro forma condensed combined financial information for the six months ended January 31, 2018 included herein was derived from our unaudited interim consolidated financial statements. We have a fiscal year end of July 31 whereas Cyence has historically had a fiscal year end of January 31 and ISCS has historically had a fiscal year end of December 31. In order to conform the Cyence historical financial information to our fiscal year end and quarter end, the Cyence historical financial information included herein is derived from the Cyence historical results for the twelve months ended July 31, 2017 and from August 1, 2017 through October 31, 2017. In order to conform the ISCS historical financial information to our fiscal year end, the ISCS historical financial information included herein is derived from the ISCS historical results from August 1, 2016 through February 15, 2017, the ISCS Acquisition Date. Additionally, we have reclassified certain line items within the historical financial information of Cyence and ISCS to conform to the presentation of our consolidated financial statements.

The historical condensed combined financial information has been adjusted to give effect to pro forma events are (1) directly attributable to the Acquisitions, (2) factually supportable, and (3) with respect to the unaudited pro forma condensed combined statements of operations, expected to have a continuing impact on the combined results. The unaudited pro forma condensed combined financial information should be read in conjunction with the following:

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The unaudited pro forma adjustments are not necessarily indicative of or intended to represent the results that would have been achieved had the Acquisitions been consummated as of the dates indicated or that may be achieved in the future. The actual results reported by the combined company in periods following the Acquisitions may differ significantly from that are reflected in the unaudited pro forma condensed combined financial information for a number of reasons, including the effects of applying final purchase accounting and the incremental costs incurred to integrate the companies. The unaudited pro forma condensed combined financial information does not reflect any cost savings or associated costs to achieve such savings from operating efficiencies, synergies, or other restructuring that may result from the Acquisitions.

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GUIDEWIRE SOFTWARE, INC.

UNAUDITED PRO FORMA CONDENSED COMBINED STATEMENT OF OPERATIONS

FOR THE SIX MONTHS ENDED JANUARY 31, 2018

(in thousands, except share and per share amounts)

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GUIDEWIRE SOFTWARE, INC.

UNAUDITED PRO FORMA CONDENSED COMBINED STATEMENT OF OPERATIONS

FOR THE YEAR ENDED JULY 31, 2017

(in thousands, except share and per share amounts)

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GUIDEWIRE SOFTWARE, INC.

NOTES TO UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

ISCS Acquisition

On February 16, 2017, we completed our acquisition of ISCS (“ISCS Acquisition”), a privately-held company that provides a cloud-based, all-in-one system for policy administration, billing and claims management to P&C insurers. The purchase price of the ISCS Acquisition was approximately $160 million, subject to certain adjustments including a net working capital adjustment, which resulted in cash consideration paid of $154.9 million. The fair value of all assets acquired and liabilities assumed will be finalized by the fiscal quarter ending April 30, 2018.

Cyence Acquisition

On November 1, 2017, the Company completed its acquisition of Cyence, Inc. (“Cyence”) for an aggregate consideration of approximately $260.3 million, subject to certain adjustments including a net working capital adjustment (the “Cyence Acquisition”). Cyence is a software company that applies data science and risk analytics to enable P&C insurers to grow by underwriting 21st century risks that have gone underinsured or uninsured. The Cyence Acquisition is intended to service the strategic needs of the P&C industry. The purchase price allocation recorded as of January 31, 2018 are preliminary and may change as we finalize these adjustments during the measurement period based on new information as it becomes available.

The historical financial information has been adjusted to give pro forma effect to events that are: (a) directly attributable to the Acquisitions, (b) factually supportable, and (c) with respect to the unaudited pro forma condensed combined statements of operations, expected to have a continuing impact on the combined results. The unaudited pro forma adjustments are preliminary and based on estimates of the fair value and useful lives of the assets acquired and liabilities assumed, and have been prepared to illustrate the estimated effect of the Acquisitions. The final determination of the purchase price allocation will be based on the final valuation of the fair values of assets acquired and liabilities assumed.

The Acquisitions have already been reflected in our historical unaudited condensed consolidated balance sheet as of January 31, 2018; therefore, no unaudited pro forma condensed combined balance sheet as of January 31, 2018 has been presented herein.

The unaudited pro forma condensed combined financial information for the year ended July 31, 2017 included herein was derived from our audited historical consolidated financial statements and the unaudited pro forma condensed combined financial information for the six months ended January 31, 2018 included herein was derived from our unaudited interim consolidated financial statements. We have a fiscal year end of July 31 whereas Cyence has historically had a fiscal year end of January 31 and ISCS has historically had a fiscal year end of December 31. In order to conform the Cyence historical financial information to our fiscal year end and quarter end, the Cyence historical financial information included herein is derived from the Cyence historical results for the twelve months ended July 31, 2017 and from August 1, 2017 to the Cyence Acquisition Date. In order to conform the ISCS historical financial information to our fiscal year end, the ISCS historical financial information included herein is derived from the ISCS historical results from August 1, 2016 to the ISCS Acquisition Date. Additionally, we have reclassified certain line items within the historical financial information of Cyence and ISCS to conform to the presentation of our consolidated financial statements.

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The unaudited pro forma condensed combined statements of operations for the six months ended January 31, 2018 reflect pro forma adjustments to our results of operations to give effect to the Cyence Acquisition as if it had occurred on August 1, 2016. In addition, the unaudited pro forma condensed combined statement of operations for the year ended July 31, 2017 give effect to the Acquisitions as if they had occurred on August 1, 2016, the first day of our 2017 fiscal year. The pro forma condensed combined financial statements were prepared using:

Adjustments to the unaudited pro forma condensed combined statements of operations for the six months ended January 31, 2018 and for the fiscal year ended July 31, 2017 (in thousands):

ISCS Pro Forma Adjustments

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Cyence Pro Forma Adjustments

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Pro forma basic and diluted weighted average earnings per share:

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