Guidewire Software : 2023 Additional Supplemental Materials – Board Diversity

970 Park Pl, Suite 200

San Mateo, CA 94403 USA

main 650-357-9100

fax [phone]

December 1, 2023

Dear Stockholder,

On November 2, 2023, Guidewire Software, Inc. (the "Company") filed its definitive proxy statement (the "Proxy Statement") for its 2023 Annual Meeting of Stockholders to be held on December 19, 2023 (the "2023 Annual Meeting") with the U.S. Securities and Exchange Commission (the "SEC"). In connection with the 2023 Annual Meeting, stockholders are being asked to, among other proposals, elect Margaret Dillon, as described in "Proposal One: Election of Directors" in the Proxy Statement.

On November 27, 2023, Glass Lewis, a proxy advisory firm, issued voting recommendations relating to the Annual Meeting. Glass Lewis recommended voting against Ms. Dillon's nomination for election to the board of directors based on what they deemed to be insufficient disclosure of board demographic information.

The Company now makes this Report Feedback Statement in response to Glass Lewis' analysis of the nomination of Ms. Dillon and provides supplemental disclosure in Exhibit Ahereto, which will be filed with the SEC as of the date hereof. The Company requests stockholders consider this supplement as they review the Glass Lewis report, as we have provided additional clarity to the previous disclosures. The Company expects to evolve and enhance its disclosures about board diversity in response to feedback from you, our stockholders.

Sincerely,

Winston King

Chief Administrative Officer, General Counsel, and Secretary

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Exhibit A

GGUIDEWIRE SOFTWARE, INC.

970 Park Pl, Suite 200, San Mateo, California 94403

Supplement to the Proxy Statement Dated November 2, 2023 for the Guidewire Software, Inc.

Annual Meeting of Stockholders to be held on December 19, 2023

Explanatory Note

This supplement (the "Supplement") supplements the definitive proxy statement filed by Guidewire Software, Inc. (the "Company") on November 2, 2023 (the "Proxy Statement") in connection with its 2023 Annual Meeting of Stockholders to be held on December 19, 2023 (the "2023 Annual Meeting").

Supplemental Disclosures

In response to recent feedback from a proxy advisory firm, the Company is providing additional clarity regarding its directors' diversity.

The Company expects to evolve and enhance its disclosures about Board diversity in response to feedback from stockholders. The following tables provide information concerning the Company's director nominees as self-reported during our fiscal year 2023.

Average Director Age	Average Director	Board Diversity in		Board Diversity in
	Tenure	Gender	Underrepresented Communities(11)
				37.50%		25.00%
				(two of eight directors self-identified as
60 years		6.46 years	(three of eight directors
	members of underrepresented
				self-identified as women)
					communities)
	Marcus S.	Paul	Mike	David S.	Margaret	Michael C.	Catherine P.	Rajani
Board Skill	Ryu	Lavin	Rosenbaum	Bauer	Dillon	Keller	Lego	Ramanathan
Scaling a SaaS	X		X	X				X
business(1)
Modern cloud			X	X				X
technologist(2)
Cybersecurity and			X	X		X		X
infrastructure(3)
Insurance industry(4)	X	X	X		X	X
Enterprise sales(5)	X	X	X			X
Investment(6)			X	X	X		X	X
CEO experience(7)	X	X	X
Financial(8)	X	X			X		X
People and	X	X	X		X	X	X	X
compensation(9)
Governance, risk, and	X	X	X	X	X	X	X	X
compliance(10)

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	Marcus S.	Paul	Mike	David S.	Margaret	Michael C.	Catherine P.	Rajani
	Ryu	Lavin	Rosenbaum	Bauer	Dillon	Keller	Lego	Ramanathan
Years on Board	22	10	4	1	4	4	4	2
Age	50	61	52	63	64	63	67	56
Gender	M	M	M	M	F	M	F	F
Self-identify as
member of an	Y (Asian)	N	N	N	N	N	N	Y (Asian)
underrepresented
community(11)
Veteran/Military	N	N	Y	N	N	N	N	N
Service(12)

1. Experience growing successful SaaS companies, including scale, margin expansion, and maturity.
2. Knowledge and experience in technology architecture, including SaaS, cloud-based platforms, integrated solutions, and customers' data journey.
3. Insight in cybersecurity risk, technology infrastructure, business prioritization, and customer drivers.
4. Insight and experience in the P&C Insurance Industry globally.
5. Knowledge and experience managing sales and selling core enterprise software/SaaS offerings.
6. Experience creating long-term value through investment, acquisitions, and growth strategies.
7. Expertise shaping strategy, performance, prioritization, and scale leadership.
8. Experience in financial strategy, accounting, and reporting.
9. Expertise in aligning company customer, performance, rewards, and talent with strategy as well as remote and flexible work strategies.
10. Experience in public company corporate governance, privacy, compliance, policy, activism, and creating long-term sustainable value.
11. The term "underrepresented community," as used herein, means Black, African American, Hispanic, Latinx, Asian, Pacific Islander, Native American, Native Hawaiian, Alaska Native, Two or More Races, or LGBTQ+.
12. The term "Veteran/Military Service" as used herein, means current full-time active duty with the U.S. Armed Forces, or any past service on active duty in the U.S. Armed Forces, Reserves, or National Guard.

Except as described above, this Supplement does not modify, amend, supplement, or otherwise affect the Proxy Statement. The Proxy Statement contains important information, and this Supplement should be read in conjunction with the Proxy Statement. The Proxy Statement, this Supplement and the Company's Annual Report on Form 10-K for the fiscal year ended July 31, 2023 are available at www.proxyvote.com.

Proxy Voting

If you have already voted, you do not need to vote again unless you would like to change or revoke your prior vote on any proposal. If you have not already voted, you are urged to vote as soon as possible. If you would like to change or revoke your prior vote on any proposal or to vote, please refer to the Proxy Statement for instructions on how to do so.

The 2023 Annual Meeting will be held virtually via a live interactive audio webcast on the Internet. You will be able to vote and submit your questions while attending the 2023 Annual Meeting online at www.virtualshareholdermeeting.com/GWRE2023.

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