Document:

Second Amended and Restated Investors' Rights Agreement

 Exhibit 4.2 
 GUIDEWIRE SOFTWARE, INC. 
 SECOND AMENDED AND RESTATED 

INVESTORS’ RIGHTS AGREEMENT 
 SEPTEMBER 20, 2007 

 TABLE OF CONTENTS 

 

							
	 	  	 	  	Page	 
		
	 1.      Registration Rights
	  	 	2	  
	 1.1
	  	Definitions	  	 	2	  
	 1.2
	  	Request for Registration	  	 	2	  
	 1.3
	  	Company Registration	  	 	4	  
	 1.4
	  	Obligations of the Company	  	 	4	  
	 1.5
	  	Furnish Information	  	 	6	  
	 1.6
	  	Expenses of Demand Registration	  	 	6	  
	 1.7
	  	Expenses of Company Registration	  	 	6	  
	 1.8
	  	Underwriting Requirements	  	 	6	  
	 1.9
	  	Delay of Registration	  	 	7	  
	 1.10
	  	Indemnification	  	 	7	  
	 1.11
	  	Reports Under the 1934 Act	  	 	9	  
	 1.12
	  	Form S-3 Registration	  	 	10	  
	 1.13
	  	Assignment of Registration Rights	  	 	11	  
	 1.14
	  	Limitations on Subsequent Registration Rights	  	 	11	  
	 1.15
	  	“Market Stand-Off” Agreement	  	 	11	  
	 1.16
	  	Termination of Registration Rights	  	 	12	  
		
	 2.      Covenants of the Company
	  	 	12	  
	 2.1
	  	Delivery of Financial Statements	  	 	12	  
	 2.2
	  	Inspection Rights	  	 	13	  
	 2.3
	  	Termination of Information Covenants	  	 	13	  
	 2.4
	  	Right of First Offer	  	 	13	  
	 2.5
	  	Stock Issuances to Employees	  	 	15	  
	 2.6
	  	Proprietary Information and Inventions Agreements	  	 	15	  
	 2.7
	  	Reimbursement of Director Expenses	  	 	15	  
	 2.8
	  	Administration of 2006 Stock Option/Stock Issuance Plan	  	 	16	  
	 2.9
	  	Termination of Certain Covenants	  	 	16	  
		
	 3.      Miscellaneous
	  	 	16	  
	 3.1
	  	Successors and Assigns	  	 	16	  
	 3.2
	  	Governing Law	  	 	16	  
	 3.3
	  	Counterparts	  	 	16	  
	 3.4
	  	Titles and Subtitles	  	 	16	  
	 3.5
	  	Notices	  	 	16	  
	 3.6
	  	Expenses	  	 	17	  
	 3.7
	  	Amendments and Waivers	  	 	17	  
	 3.8
	  	Severability	  	 	17	  
	 3.9
	  	Aggregation of Stock	  	 	17	  
	 3.10
	  	Entire Agreement	  	 	17	  
	 3.11
	  	Termination of Prior Agreement	  	 	18	  
	 3.12
	  	Additional Investors	  	 	18	  

  
 i 

 SECOND AMENDED AND RESTATED 

INVESTORS’ RIGHTS AGREEMENT 
 THIS SECOND AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT is made as of the 20th day of September, 2007, by and among Guidewire Software, Inc., a Delaware corporation (the “Company”),
John Raguin, Marcus Ryu, Ken Branson, John Seybold, Mark Shaw and James Kwak (each, a “Founder” and collectively, the “Founders”) and the investors listed on Exhibit A hereto (each, an
“Investor” and collectively, the “Investors”). 
 RECITALS 

WHEREAS, certain of the Investors (the “Existing Investors”) hold shares of the
Company’s Series A Preferred Stock (the “Series A Preferred Stock”) or Series B Preferred Stock (the “Series B
Preferred Stock”) and/or shares of Common Stock issued upon conversion thereof and possess registration rights, information rights, rights of first offer and other rights pursuant to an Amended and Restated Investors’ Rights
Agreement dated as of October 6, 2004 by and among the Company, the Founders and such Existing Investors, as amended (the “Prior Agreement”); 
 WHEREAS, the Prior Agreement may be amended, and any provision therein waived, with the consent of the Company and the holders of more than 50% of the outstanding Registrable Securities (as such
term is defined in the Prior Agreement) then outstanding which are not held by the Founders; 
 WHEREAS, the Existing
Investors as holders of more than 50% of the outstanding Registrable Securities (as such term is defined in the Prior Agreement) of the Company not held by the Founders desire to terminate the Prior Agreement and to accept the rights, created
pursuant hereto in lieu of the rights granted to them under the Prior Agreement; and 
 WHEREAS, certain Investors are
parties to the Series C Preferred Stock Purchase Agreement of even date herewith by and among the Company and certain of the Investors (the “Series C Agreement”), which provides that as a condition to the
closing of the sale of the Series C Preferred Stock (the “Series C Preferred Stock,” collectively with the Series A Preferred Stock and Series B Preferred Stock, the “Preferred Stock”), this Agreement
must be executed and delivered by such Investors, Existing Investors holding more than 50% of the outstanding Registrable Securities (as such term is defined in the Prior Agreement) of the Company not held by the Founders, the Founders, and the
Company. 

 NOW, THEREFORE, THE PARTIES HEREBY AGREE AS FOLLOWS: 

1. Registration Rights. The Company covenants and agrees as follows: 

1.1 Definitions. For purposes of this Section 1: 

(a) The term “Act” means the Securities Act of 1933, as amended. 

(b) The term “Form S-3” means such form under the Act as in effect on the date hereof or any
registration form under the Act subsequently adopted by the SEC that permits inclusion or incorporation of substantial information by reference to other documents filed by the Company with the SEC. 

(c) The term “Holder” means any person owning or having the right to acquire Registrable
Securities or any assignee thereof in accordance with Section 1.13 hereof. 
 (d) The term “1934
Act” shall mean the Securities Exchange Act of 1934, as amended. 
 (e) The term
“register,” “registered” and “registration” refer to a registration effected by preparing and filing a registration statement or similar document in compliance with the Act, and
the declaration or ordering of effectiveness of such registration statement or document. 
 (f) The term
“Registrable Securities” means: (i) any Common Stock issued or issuable upon conversion of the Preferred Stock of the Company; (ii) for purposes of the rights granted pursuant to Section 1.3 of this Agreement
only, any Common Stock held by a Founder (other than Common Stock held by a Founder issued upon conversion of the Preferred Stock held by such Founder, which Common Stock shall be deemed Registrable Securities as set forth in clause (i) above);
and (iii) any Common Stock of the Company issued as (or issuable upon the conversion or exercise of any warrant, right or other security that is issued as) a dividend or other distribution with respect to, or in exchange for, or in replacement
of, such Preferred Stock or Common Stock, excluding, however, any Registrable Securities sold by a person in a transaction in which such person’s rights under this Section 1 are not assigned. 

(g) The number of shares of “Registrable Securities then outstanding” shall mean the number of
shares of Common Stock that are Registrable Securities and (i) are then issued and outstanding or (ii) are then issuable pursuant to the exercise or conversion of then outstanding and then exercisable options, warrants or convertible
securities. 
 (h) The term “SEC” shall mean the Securities and Exchange Commission.

 1.2 Request for Registration. 

(a) If the Company shall receive at any time subsequent to the earlier of (i) September 30, 2011, or
(ii) six months following the completion of the Company’s firm commitment underwritten initial public offering, a written request from the Holders not less than 50% of the Registrable Securities then outstanding that would result in the
filing of a registration statement under the Act covering the registration of such Registrable Securities having an aggregate offering price to the public of at least $5,000,000, then the Company shall: 

(i) within fifteen (15) days of the receipt thereof, give written notice of such request to all Holders; and

  
 2 

 (ii) use its best efforts to file, and reasonable, diligent efforts to
effect, as soon as practicable, and in any event to file the initial registration statement in connection therewith within 90 days of the receipt of such request, the registration under the Act of all Registrable Securities that the Holders request
to be registered within 20 days of the mailing of notice by the Company referenced in Section 1.2(a)(i) above, subject to the limitations of subsection 1.2(b). 

(b) If the Holders initiating the registration request hereunder (the “Initiating Holders”) intend
to distribute the Registrable Securities covered by their request by means of an underwriting, they shall so advise the Company as a part of their request made pursuant to subsection 1.2(a) and the Company shall include such information in the
written notice referred to in subsection 1.2(a)(i). The underwriter will be selected by a majority in interest of the Initiating Holders and shall be reasonably acceptable to the Company. In such event, the right of any Holder to include such
Holder’s Registrable Securities in such registration shall be conditioned upon such Holder’s participation in such underwriting and the inclusion of such Holder’s Registrable Securities in the underwriting (unless otherwise mutually
agreed by a majority in interest of the Initiating Holders and such Holder) to the extent provided herein. All Holders proposing to distribute their securities through such underwriting shall (together with the Company as provided in subsection
1.4(e)) enter into an underwriting agreement in customary form with the underwriter or underwriters selected for such underwriting. Notwithstanding any other provision of this Section 1.2, if the underwriter advises the Initiating Holders in
writing that marketing factors require a limitation of the number of shares to be underwritten, then the Initiating Holders shall so advise all Holders of Registrable Securities that would otherwise be underwritten pursuant hereto, and the number of
shares of Registrable Securities that may be included in the underwriting shall be allocated among all Holders thereof, including the Initiating Holders, in proportion (as nearly as practicable) to the amount of Registrable Securities of the Company
owned by each Holder; provided, however, that the number of shares of Registrable Securities held by Initiating Holders to be included in such underwriting shall not be reduced unless all securities other than Registrable Securities are first
entirely excluded from the underwriting. 
 (c) Notwithstanding the foregoing, if the Company shall furnish to
Holders requesting a registration statement pursuant to this Section 1.2, a certificate signed by the Chief Executive Officer of the Company stating that in the good faith judgment of the Board of Directors of the Company, it would be seriously
detrimental to the Company and its stockholders for such registration statement to be filed, the Company shall have the right to defer taking action with respect to such filing for a period not to exceed 90 days after receipt of the request of the
Initiating Holders; provided, however, that the Company may not utilize this right more than once in any twelve-month period. 

  
 3 

 (d) In addition, the Company shall not be obligated to effect, or to take
any action to effect, any registration pursuant to this Section 1.2: 
 (i) After the Company has effected
two (2) registrations pursuant to this Section 1.2 and such registrations have been declared or ordered effective; 
 (ii) Within six (6) months after any other registration by the Company under the Act; 
 (iii) During the period starting with the date ninety (90) days prior to the Company’s good faith estimate of the date of filing of, and ending on a date one hundred and eighty (180) days
after the effective date of a registration subject to Section 1.3 hereof; provided that the Company is actively employing in good faith all reasonable efforts to cause such registration statement to become effective and the Company
delivers notice of such intent to the Initiating Holders within thirty (30) days of the registration request; or 
 (iv) If the Initiating Holders propose to dispose of shares of Registrable Securities that may be immediately registered on Form S-3 pursuant to a request made pursuant to Section 1.12 below.

 1.3 Company Registration. If (but without any obligation to do so) the Company proposes to register for
its own account any of its capital stock or other securities under the Act in connection with the public offering of such securities solely for cash (other than a registration relating solely to the sale of securities to participants in a Company
stock plan, a registration on any form that does not include substantially the same information as would be required to be included in a registration statement covering the sale of the Registrable Securities or a registration in which the only
Common Stock being registered is Common Stock issuable upon conversion of debt securities that are also being registered or an SEC Rule 145 transaction), the Company shall, at such time, promptly give each Holder written notice of such registration.
Upon the written request of each Holder given within twenty (20) days after mailing of such notice by the Company in accordance with Section 3.5, the Company shall, subject to the provisions of Section 1.8, use its best efforts to
cause to be registered under the Act all of the Registrable Securities that each such Holder has requested to be registered. 
 1.4 Obligations of the Company. Whenever required under this Section 1 to effect the registration of any Registrable Securities, the Company shall, as expeditiously as reasonably possible:

 (a) Prepare and file with the SEC a registration statement with respect to such Registrable Securities and
use its best efforts to cause such registration statement to become effective, and, upon the request of the Holders of a majority of the Registrable Securities registered thereunder, keep such registration statement effective for a period of up to
one hundred twenty (120) days or until the distribution contemplated in the Registration Statement has been completed; provided, however, that (i) such 120-day period shall be extended for a period of time equal to the period the
Holder refrains from selling any securities included in such registration at the request of an underwriter of Common Stock (or other securities) of the Company; and (ii) in the case of any registration of Registrable Securities on Form S-3 that
are intended to be offered on a continuous or delayed basis, such 120-day period shall be extended, if necessary, to keep the registration statement effective until all such Registrable Securities are

  
 4 

 
sold, provided that Rule 415, or any successor rule under the Act, permits an offering on a continuous or delayed basis, and provided further that applicable rules under the Act governing the
obligation to file a post-effective amendment permit, in lieu of filing a post-effective amendment that (x) includes any prospectus required by Section 10(a)(3) of the Act or (y) reflects facts or events representing a material or
fundamental change in the information set forth in the registration statement, the incorporation by reference of information required to be included in (x) and (y) above to be contained in periodic reports filed pursuant to Section 13
or 15(d) of the 1934 Act in the registration statement. 
 (b) Prepare and file with the SEC such amendments and
supplements to such registration statement and the prospectus used in connection with such registration statement as may be necessary to comply with the provisions of the Act with respect to the disposition of all securities covered by such
registration statement. 
 (c) Furnish to the Holders such numbers of copies of a prospectus, including a
preliminary prospectus, in conformity with the requirements of the Act, and such other documents as they may reasonably request to facilitate the disposition of Registrable Securities owned by them. 

(d) Use its best efforts to register and qualify the securities covered by such registration statement under such other
securities or Blue Sky laws of such jurisdictions as shall be reasonably requested by the Holders; provided that the Company shall not be required in connection therewith or as a condition thereto to qualify to do business or to file a general
consent to service of process in any such states or jurisdictions, except as may be required by the Act. 
 (e)
In the event of any underwritten public offering, enter into and perform its obligations under an underwriting agreement, in usual and customary form, with the managing underwriter of such offering. Each Holder participating in such underwriting
shall also enter into and perform its obligations under such an agreement. 
 (f) Notify each Holder of
Registrable Securities covered by such registration statement at any time when a prospectus relating thereto is required to be delivered under the Act of the happening of any event as a result of which the prospectus included in such registration
statement, as then in effect, includes an untrue statement of a material fact or omits to state a material fact required to be stated therein or necessary to make the statements therein not misleading in the light of the circumstances then existing.

 (g) Cause all such Registrable Securities registered under this Section 1 to be listed on each
securities exchange on which similar securities issued by the Company are then listed. 
 (h) Provide a transfer
agent and registrar for all Registrable Securities registered pursuant to this Section 1 and a CUSP number for all such Registrable Securities, in each case not later than the effective date of such registration. 

  
 5 

 (i) Furnish, at the request of any Holder requesting registration of
Registrable Securities pursuant to this Section 1, on the date that such Registrable Securities are delivered to the underwriters for sale in connection with a registration pursuant to this Section 1, if such securities are being sold
through underwriters, or, if such securities are not being sold through underwriters, on the date that the registration statement with respect to such securities becomes effective, an opinion, dated such date, of the counsel representing the Company
for the purposes of such registration, in form and substance as is customarily given to underwriters in an underwritten public offering, addressed to the underwriters, if any, and to the Holders requesting registration of Registrable Securities.

 1.5 Furnish Information. It shall be a condition precedent to the obligations of the Company to take
any action pursuant to this Section 1 with respect to the Registrable Securities of any selling Holder that such Holder shall furnish to the Company such information regarding itself, the Registrable Securities held by it, and the intended
method of disposition of such securities as shall be required to effect the registration of such Holder’s Registrable Securities. 
 1.6 Expenses of Demand Registration. All expenses (other than underwriting discounts and commissions, Blue Sky fees, stock transfer taxes and fees) incurred in connection with registrations,
filings or qualifications pursuant to Section 1.2, including (without limitation) all registration, filing and qualification fees, printers’ and accounting fees, and fees and disbursements of counsel for the Company and the reasonable fees
and expenses of one counsel for the selling stockholders (not to exceed $15,000) shall be borne by the Company; provided, however, that the Company shall not be required to pay for any expenses of any registration proceeding begun pursuant to
Section 1.2 if the registration request is subsequently withdrawn at the request of the Holders of a majority of the Registrable Securities to be registered (in which case all participating Holders shall bear such expenses), unless the Holders
of a majority of the Registrable Securities agree to forfeit their right to one demand registration pursuant to Section 1.2; provided further, however, that if at the time of such withdrawal, the Holders (i) have learned of a
material adverse change in the condition, business or prospects of the Company that was not known to the Holders at the time of their request and (ii) have withdrawn the request with reasonable promptness following disclosure by the Company of
such material adverse change, then the Holders shall not be required to pay any such expenses and shall retain their rights pursuant to Section 1.2. 
 1.7 Expenses of Company Registration. The Company shall bear and pay all expenses incurred in connection with any registration, filing or qualification of Registrable Securities with respect to the
registrations pursuant to Section 1.3 for each Holder (which right may be assigned as provided in Section 1.13), including (without limitation) all registration, filings and qualification fees, printers’ and accounting fees and fees
and disbursements of counsel for the Company, and the reasonable fees and expenses of one counsel for the selling stockholders (not to exceed $15,000), but excluding underwriting discounts and commissions, Blue Sky fees, stock transfer taxes and
fees and expenses of counsel to the Holders other than as set forth above. 
 1.8 Underwriting
Requirements. If a registration statement for which the Company gives notice pursuant to Section 1.3 is for an underwritten offering, then the Company shall so advise the Holders of Registrable Securities. In such event, the right of any
Holder’s Registrable Securities to be included in a registration pursuant to Section 1.3 shall be 

  
 6 

 
conditioned upon such Holder’s participation in such underwriting and the inclusion of such Holder’s Registrable Securities in the underwriting to the extent provided herein. All
Holders proposing to distribute their Registrable Securities through such underwriting shall enter into an underwriting agreement in customary form with the managing underwriter or underwriter(s) selected for such underwriting. Notwithstanding any
other provision of this Agreement, if the managing underwriter(s) determine(s) in good faith that marketing factors require a limitation of the number of shares to be underwritten, then the managing underwriter(s) may exclude shares (including
Registrable Securities) from the registration and the underwriting, and the number of shares that may be included in the registration and the underwriting shall be allocated first, to the Company, and second, to each of the Holders
requesting inclusion of their Registrable Securities in such registration statement on a pro rata basis based upon the total number of Registrable Securities then held by each such Holder; provided, however, that in no event shall the amount
of securities of the selling Holders included in such registration be reduced below twenty five percent (25%) of the total amount of securities included in such offering, unless such offering is the initial public offering of the Company’s
securities in which case the Holders may be excluded in their entirety; provided further, however, that in no event shall the amount of securities of the selling Holders who are not Founders included in such registration be reduced unless all
shares held by the Founders are first excluded from such registration (other than shares of Common Stock held by a Founder as a result of the conversion of shares of Preferred Stock held by such Founder in his capacity as an Investor herewith). If
any Holder disapproves of the terms of any such underwriting, such Holder may elect to withdraw therefrom by written notice to the Company and the underwriter, delivered at least 15 business days prior to the effective date of the registration
statement. Any Registrable Securities excluded or withdrawn from such underwriting shall be excluded and withdrawn from the registration. For any Holder that is a partnership or corporation, the partners, retired partners and stockholders of such
Holder, or the estates and family members of any such partners, stockholders and retired partners and any trusts for the benefit of any of the foregoing persons shall be deemed to be a single “Holder,” and any pro rata reduction with
respect to such “Holder” shall be based upon the aggregate amount of shares carrying registration rights owned by all entities and individuals included in such “Holder,” as defined in this sentence. 

1.9 Delay of Registration. No Holder shall have any right to obtain or seek an injunction restraining or otherwise
delaying any such registration as the result of any controversy that might arise with respect to the interpretation or implementation of this Section 1. 
 1.10 Indemnification. In the event any Registrable Securities are included in a registration statement under this Section 1: 

(a) To the extent permitted by law, the Company will indemnify and hold harmless each Holder, any underwriter (as defined
in the Act) for such Holder and each person, if any, who controls such Holder or underwriter within the meaning of the Act or the 1934 Act, against any losses, claims, damages or liabilities (joint or several) to which they may become subject under
the Act, the 1934 Act or other federal or state law, insofar as such losses, claims, damages or liabilities (or actions in respect thereof) arise out of or are based upon any of the following statements, omissions or violations (collectively a
“Violation”): (i) any untrue statement or alleged untrue statement of a material fact contained in such 

  
 7 

 
registration statement, including any preliminary prospectus or final prospectus contained therein or any amendments or supplements thereto, (ii) the omission or alleged omission to state
therein a material fact required to be stated therein, or necessary to make the statements therein not misleading, or (iii) any violation or alleged violation by the Company of the Act, the 1934 Act, any state securities law or any rule or
regulation promulgated under the Act, the 1934 Act or any state securities law; and the Company will pay to each such Holder, underwriter or controlling person any legal or other expenses reasonably incurred by them in connection with investigating
or defending any such loss, claim, damage, liability or action; provided, however, that the indemnity agreement contained in this subsection 1.10(a) shall not apply to amounts paid in settlement of any such loss, claim, damage, liability or
action if such settlement is effected without the consent of the Company (which consent shall not be unreasonably withheld), nor shall the Company be liable in any such case for any such loss, claim, damage, liability or action to the extent that it
arises out of or is based upon a Violation that occurs in reliance upon and in conformity with written information furnished expressly for use in connection with such registration by any such Holder, underwriter or controlling person. 

(b) To the extent permitted by law, each selling Holder will indemnify and hold harmless the Company, each of its
directors, each of its officers who has signed the registration statement, each person, if any, who controls the Company within the meaning of the Act, any underwriter, any other Holder selling securities in such registration statement and any
controlling person of any such underwriter or other Holder, against any losses, claims, damages or liabilities (joint or several) to which any of the foregoing persons may become subject, under the Act, the 1934 Act or other federal or state law,
insofar as such losses, claims, damages or liabilities (or actions in respect thereto) arise out of or are based upon any Violation, in each case to the extent (and only to the extent) that such Violation occurs in reliance upon and in conformity
with written information furnished by such Holder expressly for use in connection with such registration; and each such Holder will pay any legal or other expenses reasonably incurred by any person intended to be indemnified pursuant to this
subsection 1.10(b), in connection with investigating or defending any such loss, claim, damage, liability or action; provided, however, that the indemnity agreement contained in this subsection 1.10(b) shall not apply to amounts paid in
settlement of any such loss, claim, damage, liability or action if such settlement is effected without the consent of the Holder, which consent shall not be unreasonably withheld; provided, further, that in no event shall any indemnity under
this subsection 1.10(b) exceed the net proceeds from the offering received by such Holder. 
 (c) Promptly after
receipt by an indemnified party under this Section 1.10 of notice of the commencement of any action (including any governmental action), such indemnified party will, if a claim in respect thereof is to be made against any indemnifying party
under this Section 1.10, deliver to the indemnifying party a written notice of the commencement thereof and the indemnifying party shall have the right to participate in, and, to the extent the indemnifying party so desires, jointly with any
other indemnifying party similarly noticed, to assume the defense thereof with counsel mutually satisfactory to the parties; provided, however, that an indemnified party (together with all other indemnified parties that may be represented
without conflict by one counsel) shall have the right to retain one separate counsel, with the fees and expenses to be paid by the indemnifying party, if representation of such indemnified party by the counsel retained by the indemnifying party
would be inappropriate due to actual or potential differing interests between such indemnified party and any other party 

  
 8 

 
represented by such counsel in such proceeding. The failure to deliver written notice to the indemnifying party within a reasonable time of the commencement of any such action, if prejudicial to
its ability to defend such action, shall relieve such indemnifying party of any liability to the indemnified party under this Section 1.10, but the omission so to deliver written notice to the indemnifying party will not relieve it of any
liability that it may have to any indemnified party otherwise than under this Section 1.10. 
 (d) If the
indemnification provided for in this Section 1.10 is held by a court of competent jurisdiction to be unavailable to an indemnified party with respect to any loss, liability, claim, damage or expense referred to therein, then the indemnifying
party, in lieu of indemnifying such indemnified party hereunder, shall contribute to the amount paid or payable by such indemnified party as a result of such loss, liability, claim, damage or expense in such proportion as is appropriate to reflect
the relative fault of the indemnifying party on the one hand and of the indemnified party on the other in connection with the statements or omissions that resulted in such loss, liability, claim, damage or expense as well as any other relevant
equitable considerations; provided that in no event shall any contribution by a Holder under this Section 1.10(d) exceed the net proceeds from the offering received by such Holder. The relative fault of the indemnifying party and of the
indemnified party shall be determined by reference to, among other things, whether the untrue or alleged untrue statement of a material fact or the omission to state a material fact relates to information supplied by the indemnifying party or by the
indemnified party and the parties’ relative intent, knowledge, access to information and opportunity to correct or prevent such statement or omission. 
 (e) Notwithstanding the foregoing, to the extent that the provisions on indemnification and contribution contained in the underwriting agreement entered into in connection with the underwritten public
offering are in conflict with the foregoing provisions, the provisions in the underwriting agreement shall control. 
 (f) The obligations of the Company and Holders under this Section 1.10 shall survive the completion of any offering of Registrable Securities in a registration statement under this Section 1,
and otherwise. 
 1.11 Reports Under the 1934 Act. With a view to making available to the Holders the
benefits of Rule 144 promulgated under the Act and any other rule or regulation of the SEC that may at any time permit a Holder to sell securities of the Company to the public without registration or pursuant to a registration on Form S-3, the
Company agrees to: 
 (a) make and keep public information available, as those terms are understood and defined
in SEC Rule 144, at all times after the effective date of the first registration statement filed by the Company for the offering of its securities to the general public; 

(b) take such action, including the voluntary registration of its Common Stock under Section 12 of the 1934 Act, as
is necessary to enable the Holders to utilize Form S-3 for the sale of their Registrable Securities; 
 (c) file
with the SEC in a timely manner all reports and other documents required of the Company under the Act and the 1934 Act; and 

  
 9 

 (d) furnish to any Holder, so long as the Holder owns any Registrable
Securities, forthwith upon request (i) a written statement by the Company that it has complied with the reporting requirements of SEC Rule 144 (at any time after ninety (90) days after the effective date of the first registration statement
filed by the Company), the Act and the 1934 Act (at any time after it has become subject to such reporting requirements), or that it qualifies as a registrant whose securities may be resold pursuant to Form S-3 (at any time after it so qualifies),
(ii) a copy of the most recent annual or quarterly report of the Company and such other reports and documents filed under the 1934 Act by the Company, and (iii) such other information as may be reasonably requested in availing any Holder
of any rule or regulation of the SEC that permits the selling of any such securities without registration or pursuant to such form. 
 1.12 Form S-3 Registration. If the Company shall receive from any Holder or Holders a written request or requests that the Company effect a registration on Form S-3 and any related qualification or
compliance with respect to all or a part of the Registrable Securities owned by such Holder or Holders, the Company will: 
 (a) promptly give written notice of the proposed registration, and any related qualification or compliance, to all other Holders; and 

(b) use its best efforts to effect, as soon as practicable, such registration and all such qualifications and compliances
as may be so requested and as would permit or facilitate the sale and distribution of all or such portion of such Holder’s or Holders’ Registrable Securities as are specified in such request, together with all or such portion of the
Registrable Securities of any other Holder or Holders joining in such request as are specified in a written request given within fifteen (15) days after receipt of such written notice from the Company; provided, however, that the Company
shall not be obligated to effect any such registration, qualification or compliance, pursuant to this Section 1.12: (i) if Form S-3 is not available for such offering by the Holders; (ii) if the Holders, together with the holders of
any other securities of the Company entitled to inclusion in such registration, propose to sell Registrable Securities and such other securities (if any) at an aggregate price to the public (net of any underwriters’ discounts or commissions) of
less than $500,000; (iii) the Company has effected two (2) such registrations prior to the date of such request; (iv) if the Company shall furnish to the Holders a certificate signed by the President of the Company stating that in the
good faith judgment of the Board of Directors of the Company, it would be seriously detrimental to the Company and its stockholders for such Form S-3 registration to be effected at such time, in which event the Company shall have the right to defer
the filing of the Form S-3 registration statement for a period not to exceed ninety (90) days after receipt of the request of the Holder or Holders under this Section 1.12; provided, however, that the Company shall not utilize this
right more than once in any twelve month period; (v) if the Company has, within the twelve (12) month period preceding the date of such request, already effected one (1) registration pursuant to this Section 1.12; or (vi) in
any particular jurisdiction in which the Company would be required to qualify to do business or to execute a general consent to service of process in effecting such registration, qualification or compliance. 

  
 10 

 (c) Subject to the foregoing, the Company shall file a registration
statement covering the Registrable Securities and other securities so requested to be registered as soon, as practicable after receipt of the request or requests of the Holders. All expenses incurred in connection with all registrations requested
pursuant to Section 1.12, including (without limitation) all registration, filing, qualification, printers’ and accounting fees and the fees and disbursements of counsel and the reasonable fees and expenses of one counsel for the selling
stockholders for the Company (not to exceed $15,000), but excluding any underwriters’ discounts or commissions, Blue Sky fees, stock transfer taxes and fees, shall be borne by the Company. Registrations effected pursuant to this
Section 1.12 shall not be counted as demands for registration or registrations effected pursuant to Sections 1.2 or 1.3. 
 1.13 Assignment of Registration Rights. The rights to cause the Company to register Registrable Securities pursuant to this Section 1 may be assigned (but only with all related obligations) by
a Holder to a transferee or assignee of such securities provided: (a) the Company is, within a reasonable time after such transfer, furnished with written notice of the name and address of such transferee or assignee and the securities with
respect to which such registration rights are being assigned; (b) such transferee or assignee agrees in writing to be bound by and subject to the terms and conditions of this Agreement, including without limitation the provisions of
Section 1.15 below; (c) the transfer involves a transfer of at least 3,000,000 shares of Registrable Securities (as adjusted for dividends, splits, recapitalizations and the like); provided, however, that transfers or assignments to
partners, retired partners, stockholders, members, parents, children, spouses, trusts or affiliates of a Holder (each a “Qualified Transferee”) shall be without restriction as to the minimum number of shares to be
transferred; and (d) such assignment shall be effective only if immediately following such transfer the further disposition of such securities by the transferee or assignee is restricted under the Act. 

1.14 Limitations on Subsequent Registration Rights. From and after the date of this Agreement, the Company shall
not, without the prior written consent of the Holders of a majority of the outstanding Registrable Securities, enter into any agreement with any holder or prospective holder of any securities of the Company that would allow such holder or
prospective holder (a) to include such securities in any registration filed under Section 1.2 or 1.3 hereof, unless under the terms of such agreement, such holder or prospective holder may include such securities in any such registration
only to the extent that the inclusion of such holder’s securities will not reduce the amount of the Registrable Securities of the Holders that is included or (b) to make a demand registration that could result in such registration
statement being declared effective prior to the date set forth in subsection 1.2(a) or within one hundred twenty (120) days of the effective date of any registration effected pursuant to Section 1.2. 

1.15 “Market Stand-Off” Agreement. Each Investor hereby agrees that, during the period of duration
specified by the Company and an underwriter of common stock or other securities of the Company, following the effective date of an initial registration statement of the Company filed under the Act, it shall not, to the extent requested by the
Company and such underwriter, directly or indirectly sell, offer to sell, contract to sell (including, without limitation, any short sale), grant any option to purchase or otherwise transfer or dispose of (other than to donees who agree to be
similarly bound) any securities of the Company held by it at any time during such period except common stock included in such registration; provided, however, that: 

(a) all executive officers, directors and holders of at least 1% of the outstanding capital stock of the Company enter
into similar agreements; and 

  
 11 

 (b) such market stand-off time period shall not exceed one hundred eighty
(180) days plus such additional period as may reasonably be requested by the Company or such underwriter to accommodate regulatory restrictions on (i) the publication or other distribution of research reports or (ii) analyst
recommendations and opinions, including (without limitation) the restrictions set forth in Rule 2711(f)(4) of the National Association of Securities Dealers and Rule 472(f)(4) of the New York Stock Exchange, as amended, or any similar successor
rules. 
 In order to enforce the foregoing covenant, the Company may impose stop-transfer instructions with respect to the
Registrable Securities of each Investor (and the shares or securities of every other person subject to the foregoing restriction) until the end of such period. 
 Notwithstanding the foregoing, the obligations described in this Section 1.15 shall not apply to a registration relating solely to employee benefit plans on Form S-l or Form S-8 or similar forms that
may be promulgated in the future, or a registration relating solely to an SEC Rule 145 transaction. 
 1.16
Termination of Registration Rights. No Holder shall be entitled to exercise any right provided for in this Section 1 after the earlier of: (a) seven (7) years following the consummation of the sale of securities pursuant to a
registration statement filed by the Company under the Act in connection with the initial firm commitment underwritten offering of its securities to the general public or (b) such time as all Registrable Securities held by such Holder can be
sold in any three (3) month period without registration under SEC Rule 144. 
 2. Covenants of the Company.

 2.1 Delivery of Financial Statements. The Company shall deliver to each Investor, for so long as such
Investor holds (together with its affiliates) at least 1,000,000 shares (as adjusted for subsequent stock dividends, splits, recapitalizations and the like) of Preferred Stock (a “Major Investor”): 

(a) promptly after the end of each fiscal year of the Company, an income statement for such fiscal year, a balance sheet
of the Company as of the end of such year, a statement of stockholder’s equity as of the end of such year and a statement of cash flows for such fiscal year, such year-end financial reports to be in reasonable detail, prepared in accordance
with generally accepted accounting principles (“GAAP”) and audited and certified by independent public accountants selected by the Company (and approved by the Company’s Board of Directors); 

(b) promptly after the end of each month, an unaudited income statement, balance sheet and statement of cash flows for
and as of the end of such month, such unaudited financial statements to be in reasonable detail and to show a comparison against budget; and 

  
 12 

 (c) as soon as practicable, but in any event thirty (30) days prior to
the end of each fiscal year, a budget for the next fiscal year, prepared on a quarterly basis, including balance sheets, income statements and statements of cash flows and any other budgets prepared by the Company and approved by its Board of
Directors. 
 2.2 Inspection Rights. The Company shall permit each Major Investor or its transferees (as
permitted pursuant to Section 1.13 hereof), at such Major Investor’s expense, to visit and inspect the Company’s properties, to examine its books of account and records and to discuss the Company’s affairs, finances and accounts
with its officers, all at such reasonable times as may be requested by such Major Investor; provided, however, that the Company shall not be obligated under this Section 2.2 to provide information that it deems in good faith to be a
trade secret or similar confidential or proprietary information. 
 2.3 Termination of Information
Covenants. The covenants set forth in Sections 2.1 and 2.2 shall terminate as to Major Investors and be of no further force or effect (i) upon the consummation of a firm commitment underwritten public offering of the Company’s
securities, (ii) upon the closing of a Corporate Sale (as defined in the Company’s Amended and Restated Certificate of Incorporation, as amended from time to time (the “Restated Certificate”)) or (iii) when the
Company first becomes subject to the periodic reporting requirements of Sections 12(g) or 15(d) of the 1934 Act, whichever event shall first occur. 
 2.4 Right of First Offer. Subject to the terms and conditions specified in this paragraph 2.4, the Company hereby grants to each Major Investor a right of first offer with respect to future sales
by the Company of its Shares (as hereinafter defined). For purposes of this Section 2.4, a Major Investor includes any general partners and affiliates of a Major Investor. A Major Investor shall be entitled to apportion the right of first offer
hereby granted it among itself and its partners and affiliates in such proportions as it deems appropriate. 
 Each time the
Company proposes to offer any shares of, or securities convertible into or exercisable for any shares of, any class of its capital stock (“Shares”), the Company shall first make an offering of such Shares to each Major
Investor in accordance with the following provisions: 
 (a) The Company shall deliver a notice by certified
mail (“Notice”) to the Major Investors stating (i) its bona fide intention to offer such Shares, (ii) the number of such Shares to be offered, and (iii) the price and terms, if any, upon which it proposes to
offer such Shares. 
 (b) Within fifteen (15) calendar days after giving of the Notice, the Major Investor
may elect to purchase or obtain, at the price and on the terms specified in the Notice, up to that portion of such Shares that equals the proportion that the number of shares of Common Stock issued and held, or issuable upon conversion of all
convertible securities then held, by such Major Investor bears to the total number of shares of Common Stock then outstanding (assuming full conversion of all convertible securities). The Company shall promptly, in writing, inform each Major
Investor that elects to purchase all the shares available to it under this Section 2.4 (each, a “Fully-Exercising Investor”) of any other Major Investor’s failure to do likewise. During the 10-day
period commencing after receipt of such information, 

  
 13 

 
each Fully-Exercising Investor shall be entitled to obtain that portion of the Shares for which Major Investors were entitled to subscribe but which were not subscribed for by the Major Investors
that is equal to the proportion that the number of shares of Common Stock issued and held, or issuable upon conversion of all convertible securities then held, by such Fully-Exercising Investor bears to the total number of shares of Common Stock
then outstanding (assuming full conversion of all convertible securities). 
 (c) If all Shares that Major
Investors are entitled to obtain pursuant to subsection 2.4(b) are not elected to be obtained as provided in subsection 2.4(b) hereof, the Company may, during the 30 day period following the expiration of the period provided in subsection 2.4(b)
hereof, offer the remaining unsubscribed portion of such Shares to any person or persons at a price not less than, and upon terms no more favorable to the offeree than those specified in the Notice. If the Company does not enter into an agreement
for the sale of the Shares within such period, or if such agreement is not consummated within 30 days of the execution thereof, the right provided hereunder shall be deemed to be revived and such Shares shall not be offered unless first reoffered to
the Major Investors in accordance herewith. 
 (d) The right of first offer in this paragraph 2.4 shall not be
applicable (i) to the issuance or sale of shares of Series C Preferred Stock pursuant to the Series C Agreement, (ii) to the issuance or sale of stock (or options therefor) to leasing companies, landlords, lenders or other providers of
goods or services to the Company, (iii) to the issuance of Common Stock (or options therefor) to officers, directors, employees, consultants, advisors or contractors of the Company pursuant to stock option or stock purchase plans or agreements
on terms approved by the Board of Directors; (iv) to or after consummation of a bona fide, firmly underwritten public offering of shares of Common Stock, registered under the Act pursuant to a registration statement, (v) to the issuance of
securities pursuant to the conversion or exercise of convertible or exercisable securities, or (vi) to the issuance of securities in connection with a bona fide business acquisition by the Company approved by its Board of Directors, whether by
merger, consolidation, sale of assets, sale or exchange of stock or otherwise. 
 (e) The right of first offer
set forth in this Section 2.4 may not be assigned or transferred, except that (i) such right is assignable by each Major Investor to any Qualified Transferee and (ii) such right is assignable between and among any of the Major
Investors. 
 (f) The right of first offer set forth in this Section 2.4 shall terminate immediately prior
to (i) the closing of a firm commitment underwritten public offering pursuant to an effective registration statement under the Act covering the offer and sale of Common Stock (other than a registration on Form S-8, Form S-4 or comparable or
successor forms), in which all shares of Preferred Stock are converted into shares of Common Stock pursuant to the terms of the Restated Certificate; or (ii) the closing of a Corporate Sale (as defined in the Restated Certificate); provided,
however, that no such termination under clause (ii) shall be deemed to occur in connection with the sale of shares of capital stock of the Company in a transaction or series of related transactions effected primarily for equity financing
purposes. 

  
 14 

 2.5 Stock Issuances to Employees. Unless the Board of Directors so
authorizes, the Company hereby covenants that all stock, stock equivalents and options issued after the date hereof to employees of the Company shall be subject to repurchase (the “Repurchase Right”) by the Company (or its
assignees) at cost at any time during at least a sixty (60)-day period following the date on which the employee ceases for any reason (with or without cause) to remain in the service of the Company or an affiliate of the Company. The Repurchase
Right will terminate with respect to any shares for which it is not exercised within the sixty (60)-day period provided above and with respect to any shares for which the employee vests in accordance with the following vesting schedule: twenty-five
percent (25%) of the shares to vest at the expiration of one (1) year from the date of the grant if the grantee is then in the service of the Company and the remaining seventy-five percent (75%) of the shares to vest each succeeding
month in a series of thirty-six (36) successive monthly installments upon the completion by the employee of each month of service over the thirty-six (36)-month period measured from the date on which the first twenty-five percent (25%) of
the shares vested. The Company further covenants that all stock and stock equivalents issued after the date hereof to employees of the Company shall be subject to a right of first refusal (the “First Refusal Right”) by the
Company (or its assignees) in the event that the stockholder proposes to transfer or sell such stock or stock equivalents to a third party purchaser. The Repurchase Right and the First Refusal Right on any stock or stock equivalents to be granted to
officers of the Company (including officers at the vice president level and above), to the extent not exercised by the Company, shall be assigned to Major Investors pro rata based on the proportion that the number of shares of Registrable Securities
held by each such Major Investor bears to the number of Registrable Securities then outstanding and held by all Major Investors. This covenant shall lapse upon the earliest to occur of (i) the first date on which shares of common stock are held
of record by more than five hundred (500) persons; (ii) at such time as the Company first becomes subject to the periodic reporting requirements of Section 12(g) or 15(d) of the 1934 Act; (iii) a firm commitment underwritten
public offering, pursuant to an effective registration statement under the Act; (iv) the consolidation or merger of the Company (but only with respect to a consolidation or merger pursuant to which stockholders of the Company (determined prior
to such consolidation or merger) hold less than 50% of the voting equity of the surviving corporation or pursuant to which more than 50% of the voting power of the Company is transferred); or (v) the sale of all or substantially all of the
assets of the Company. 
 2.6 Proprietary Information and Inventions Agreements. The Company shall in the
future require each new officer, employee and consultant of the Company to enter into and execute a Proprietary Information and Inventions Agreement in substantially the form attached to the Purchase Agreement as Exhibit F thereof, or an agreement
containing substantially similar terms. 
 2.7 Reimbursement of Director Expenses. The Company shall
reimburse the reasonable documented expenses incurred by the directors designated by (i) the holders of Series A Preferred Stock and Series B Preferred Stock, voting together as a single class, and (ii) the Mutual Directors (as defined in
that certain Second Amended and Restated Voting Agreement of even date herewith) in connection with such directors’ attendance of meetings of the Company’s Board of Directors, promptly upon receipt of documentation of such expenses.

  
 15 

 2.8 Administration of 2006 Stock Option/Stock Issuance Plan. In
connection with the Company’s 2006 Stock Option/Stock Issuance Plan (the “Plan”) pursuant to which the Company may grant stock options, common stock, stock equivalents and similar equity interests in the
Company to employees, consultants, nonemployee directors and other service providers, the Company hereby covenants that no such grants under the Plan shall be made by the Board of Directors or any subcommittee or members thereof who are appointed to
act as the Plan Administrator (as defined in the Plan) without the approval of at least one director who was designated as a member of the Board by the holders of Series A Preferred Stock and Series B Preferred Stock, voting together as a single
class. 
 2.9 Termination of Certain Covenants. The covenants set forth in Sections 2.5, 2.6, 2.7 and 2.8
shall terminate immediately prior to (i) the closing of a firm commitment underwritten public offering pursuant to an effective registration statement under the Act covering the offer and sale of Common Stock (other than a registration on Form
S-8, Form S-4 or comparable or successor forms), in which all shares of Preferred Stock are converted into shares of Common Stock pursuant to the terms of the Restated Certificate; or (ii) the closing of a Corporate Sale (as defined in the
Restated Certificate); provided, however, that no such termination under clause (ii) shall be deemed to occur in connection with the sale of shares of capital stock of the Company in a transaction or series of related transactions effected
primarily for equity financing purposes. 
 3. Miscellaneous. 

3.1 Successors and Assigns. Except as otherwise provided herein, the terms and conditions of this Agreement shall
inure to the benefit of and be binding upon the respective successors and assigns of the parties (including transferees of any shares of Registrable Securities). Nothing in this Agreement, express or implied, is intended to confer upon any party
other than the parties hereto or their respective successors and assigns any rights, remedies, obligations or liabilities under or by reason of this Agreement, except as expressly provided in this Agreement. 

3.2 Governing Law. This Agreement shall be governed by and construed under the laws of the State of California.

 3.3 Counterparts. This Agreement may be executed in two or more counterparts, each of which shall be
deemed an original, but all of which together shall constitute one and the same instrument. 
 3.4 Titles and
Subtitles. The titles and subtitles used in this Agreement are used for convenience only and are not to be considered in construing or interpreting this Agreement. 

3.5 Notices. Unless otherwise provided, any notice required or permitted under this Agreement shall be given in
writing and shall be deemed effectively given upon personal delivery to the party to be notified or upon deposit with the United States Post Office, by registered or certified mail, postage prepaid and addressed to the party to be notified at the
address indicated for such party on the signature page hereof, or at such other address as such party may designate by ten (10) days’ advance written notice to the other parties. 

  
 16 

 3.6 Expenses. If any action at law or in equity is necessary to
enforce or interpret the terms of this Agreement, the prevailing party shall be entitled to reasonable attorneys’ fees, costs and necessary disbursements in addition to any other relief to which such party may be entitled. 

3.7 Amendments and Waivers. Any term of this Agreement may be amended and the observance of any term of this
Agreement may be waived (either generally or in a particular instance and either retroactively or prospectively), only with the written consent of the Company and the holders of more than fifty percent (50%) of the Registrable Securities then
outstanding; provided, however, that any amendment to this agreement adversely affecting the rights of the Founders under Section 1.3 hereof shall require the written consent of two-thirds (2/3) in interest of the Registrable Securities
held by the Founders; and, provided further, however, that for so long as Battery Ventures VIII, L.P. (“Battery”) holds at least 200,000 shares of Series C Preferred Stock (or 200,000 shares of Common Stock
issued upon conversion of the Series C Preferred Stock) (in each case, subject to appropriate adjustment for stock splits, stock dividends and combinations), any such amendment or waiver of the rights of Battery under Sections 2.1, 2.2 and 2.4 of
this Agreement and this Section 3.7 shall also require the written consent of Battery. In addition to the foregoing, in the event any such amendment or waiver shall uniquely and adversely affect the rights or obligations of any specific
Investor in a different manner than all of the Investors, such amendment or waiver shall require the separate written consent of a majority in interest of such Investors so uniquely and adversely affected (it being understood that, without limiting
the foregoing, different series of Preferred Stock shall not be affected differently because of proportional differences in the amounts of their respective issue prices, liquidation preferences, dividend preferences and redemption prices that arise
out of differences in the original issue price for each such series). Any amendment or waiver effected in accordance with this paragraph shall be binding upon each holder of any Registrable Securities then outstanding, each future holder of all such
Registrable Securities and the Company. 
 3.8 Severability. If any of the provisions of this Agreement
shall be held by a court or other tribunal of competent jurisdiction to be illegal, invalid or unenforceable, such provisions shall be limited or eliminated to the minimum extent, necessary so that this Agreement shall otherwise remain in full force
and effect. 
 3.9 Aggregation of Stock. All shares of Registrable Securities held or acquired by
affiliated entities or persons shall be aggregated together for the purpose of determining the availability of any rights under this Agreement. 
 3.10 Entire Agreement. This Agreement constitutes the full and entire understanding and agreement between the parties with regard to the subjects hereof. 

  
 17 

 3.11 Termination of Prior Agreement. Upon the effectiveness of this
Agreement, the Prior Agreement shall terminate and be of no further force and effect, and shall be superseded and replaced in its entirety by this Agreement. 
 3.12 Additional Investors. Notwithstanding Section 3.7, no consent shall be necessary to add additional Investors as signatories to this Agreement, provided that such Investors have purchased
Series C Preferred Stock pursuant to the subsequent closing provisions of Section 1.3 of the Series C Agreement. 

[Remainder of page intentionally left blank] 

  
 18 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

			
	COMPANY:
	
	GUIDEWIRE SOFTWARE, INC.
		
	By:	 	/s/ John Raguin
		 	John Raguin
		 	President and Chief Executive Officer

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

  

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	FOUNDERS:
	
	/s/ John Raguin
	John Raguin

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

  

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	FOUNDERS:
	
	/s/ Marcus Ryu
	Marcus Ryu

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

  

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	FOUNDERS:
	
	/s/ Kenneth W. Branson
	Ken Branson

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

  

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	INVESTORS:
	
	/s/ James Kwak
	James Kwak

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

  

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	FOUNDERS:
	
	/s/ John Seybold
	John Seybold

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

  

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	FOUNDERS:
	
	/s/ Mark Shaw
	Mark Shaw

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

			
	INVESTORS:
	
	BATTERY VENTURES VIII, L.P.
		
	By:	 	Battery Partners VIII, LLC
		 	General Partner
		
	By:	 	 /s/ Neeraj Agrawal

	Title:	 	Member Manager

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	INVESTORS:
	
	/s/ Craig Ramsey
	Craig Ramsey

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	INVESTORS:
	
	/s/ Chris Noble
	Chris Noble

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

			
	INVESTORS:
	
	U.S. VENTURE PARTNERS VIII, L.P.
	USVP VIII AFFILIATES FUND, L.P.
	USVP ENTREPRENEUR PARTNERS VIII-A, L.P.
	USVP ENTREPRENEUR PARTNERS VIII-B, L.P.
	
	 By Presidio Management Group VIII, L.L.C.
 The General Partner of Each

			
		
	By:	 	/s/ Michael P. Maher

			
	Name:	 	Michael P. Maher
	Title:	 	Attorney-in-Fact
	
	Address:
	2735 Sand Hill Road
	Menlo Park CA 94025
	Facsimile No.: (650) 854-3018
	Attn: Chief Financial Officer
	Email: deals@usvp.com

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

			
	INVESTORS:
	
	BAY PARTNERS X, L.P.
	
	 By Bay Management Company X, LLC,
 General Partner

		
	By:	 	/s/ Atul Kapadia
	Name:	 	Atul Kapadia
	Title:	 	Manager
	
	BAY PARTNERS X ENTREPRENEURS FUND, L.P.
	
	 By Bay Management Company X, LLC,
 General Partner

		
	By:	 	/s/ Atul Kapadia
	Name:	 	Atul Kapadia
	Title:	 	Manager

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	INVESTORS:
	
	/s/ John Raguin
	John Raguin

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	INVESTORS:
	
	/s/ Marcus Ryu
	Marcus Ryu

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	FOUNDERS:
	
	/s/ James Kwak
	James Kwak

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	INVESTORS:
	
	/s/ Kenneth W. Branson
	Ken Branson

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	INVESTORS:
	
	/s/ John Seybold
	John Seybold

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 IN WITNESS WHEREOF, the parties have executed this Second Amended and Restated
Investors’ Rights Agreement as of the date first above written. 
  

	
	INVESTORS:
	
	/s/ Mark Shaw
	Mark Shaw

 SIGNATURE PAGE TO GUIDEWIRE
SOFTWARE, INC. 
 SECOND AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 

 EXHIBIT A 
 Investors 
 Name 
 Battery Ventures VIII, L.P. 
 U.S. Venture Partners VIII, L.P. 

USVP VIII Affiliates Fund, L.P. 
 US VP
Entrepreneur Partners VIII-A, L.P. 
 USVP Entrepreneur Partners VIII-B, L.P. 
 Bay Partners X, L.P. 
 Bay Partners X Entrepreneurs Fund, L.P. 

Craig Ramsey 
 Chris Noble 

John Raguin 
 Marcus Ryu 

James Kwak 
 Ken Branson 

John Seybold 
 Mark Shaw 

Richard P. Branson 
 Brian Epstein 

Jonathan Epstein 
 Noah Feldman 

Michael Flexer 
 Andrew J. Harman Revocable Trust

 Barbara G. Lamparter 
 Richard A.
Lamparter 
 James W. Shaw 
 Jeff
Zajkowski 
 ExNihilo, Inc. 
 Dana
Panichas and Tommy Hansen 
 Raymond Paquin 
 Stuart Read 
 Willy HertanuWarrant to Purchase Stock

 Exhibit 4.4 
 WARRANT TO PURCHASE STOCK 
 THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AND PURSUANT TO THE PROVISIONS OF ARTICLE 5 BELOW, MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR
HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAW OR, IN THE OPINION OF LEGAL COUNSEL IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER OF THESE SECURITIES, SUCH OFFER, SALE OR TRANSFER, PLEDGE OR
HYPOTHECATION IS EXEMPT FROM REGISTRATION. 
 WARRANT TO PURCHASE STOCK 

 

			
	 Company:
	  	Guidewire Software, Inc., a Delaware corporation (the “Company”)
		
	 Number of Shares:    
	  	 (i) upon the first Advance under the Loan Agreement, this Warrant shall become exercisable for 4,967 shares of Series C Preferred
(the “Initial Shares”), and
  
 (ii) in the event the Company
achieves the Milestone and the Revolving Line is increased to $5,000,000, an additional 4,966 shares of Series C Preferred (the “Additional Shares”) shall become exercisable in the event that the first Advance under the Loan Agreement has
been made prior to such time or, if the first Advance has not yet been made, such later time as the first Advance shall be made. (subject to adjustment in the case of each of (i) and (ii) above pursuant to Section 2 hereof)

		
	 Class of Stock:
	  	Series C Preferred Stock of the Company (the “Series C Preferred”)
		
	 Warrant Price:
	  	$5.0339 per share (the “Warrant Price”)
		
	 Issue Date:
	  	March 28, 2008 (the “Issue Date”)
		
	 Expiration Date:
	  	 This Warrant shall expire (the “Expiration Date”) on the earliest to occur of as set forth in Section 1.6(b), Section 5.1
or: (i) with respect to the Initial Shares, March 28, 2015 and (ii) with respect to the Additional Shares, the earlier of (A) March 28, 2015 and (B) if the Company fails to achieve the Milestone

or the Revolving Line is not increased to $5,000,000, July 31, 2008.

		
	 Credit Facility:
	  	This Warrant is issued in connection with the Accounts Receivable Line of Credit referenced in the Loan and Security Agreement among Company and Silicon Valley Bank dated March
28, 2008 (the “Loan Agreement”)

  
 1 

 THIS WARRANT CERTIFIES THAT, for good and valuable consideration, SILICON VALLEY BANK
(“Holder”) is entitled to purchase that number of fully paid and nonassessable shares of Series C Preferred set forth above or that number of shares otherwise purchasable upon exercise of this Warrant pursuant to the provisions
herein (the “Shares”) at the Warrant Price, all as set forth above and as adjusted pursuant to Article 2 of this Warrant and subject to the provisions and upon the terms and conditions set forth in this Warrant. Capitalized terms
used but not otherwise defined herein shall have the meanings given them in the Loan Agreement. 
 ARTICLE 1. EXERCISE. 

1.1 Method of Exercise. Holder may exercise this Warrant by delivering a duly executed Notice of Exercise in substantially the
form attached as Appendix 1 (the “Notice of Exercise”) to the principal office of the Company. Unless Holder is exercising the conversion right set forth in Section 1.2, Holder shall also deliver to the Company a check, wire
transfer (to an account designated by the Company), or other form of payment acceptable to the Company for the aggregate Warrant Price for the Shares being purchased. 
 1.2 Conversion Right. In lieu of exercising this Warrant as specified in Section 1.1, Holder may from time to time convert this Warrant, in whole or in part, into a number of Shares determined
by dividing (a) the aggregate fair market value of the Shares or other securities otherwise issuable upon exercise of the portion of the Warrant being converted minus the aggregate Warrant Price of such Shares by (b) the fair market value
of one Share. The fair market value of the Shares shall be determined pursuant to Section 1.3. 
 1.3 Fair Market
Value. If the Company’s common stock is traded in a public market and the Shares are common stock, the fair market value of each Share shall be the closing price of a Share reported for the business day immediately before Holder delivers
its Notice of Exercise to the Company (or in the instance where the Warrant is exercised immediately prior to the effectiveness of the Company’s initial public offering, the “price to public” per share price specified in the final
prospectus relating to such offering). If the Company’s common stock is traded in a public market and the Shares are preferred stock, the fair market value of a Share shall be the closing price of a share of the Company’s common stock
reported for the business day immediately before Holder delivers its Notice of Exercise to the Company (or, in the instance where the Warrant is exercised immediately prior to the effectiveness of the Company’s initial public offering, the
initial “price to public” per share price specified in the final prospectus relating to such offering), in both cases, multiplied by the number of shares of the Company’s common stock into which a Share is convertible. If the
Company’s common stock is not traded in a public market, the Board of Directors of the Company shall determine fair market value in its reasonable good faith judgment. 

  
 2 

 1.4 Delivery of Certificate and New Warrant. Promptly after Holder exercises or
converts this Warrant and, if applicable, the Company receives payment of the aggregate Warrant Price, the Company shall deliver to Holder certificates for the Shares acquired and, if this Warrant has not been fully exercised or converted and has
not expired, a new Warrant representing the Shares not so acquired. 
 1.5 Replacement of Warrants. On receipt of
evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation of this Warrant and, in the case of loss, theft or destruction, on delivery of an indemnity agreement reasonably satisfactory in form and amount to the
Company or, in the case of mutilation, or surrender and cancellation of this Warrant, the Company shall execute and deliver, in lieu of this Warrant, a new warrant of like tenor. 

1.6 Treatment of Warrant Upon Acquisition of Company. 
 a. “Acquisition”. For the purpose of this Warrant, “Acquisition” means any reorganization, consolidation, or merger or other business combination of the Company where the
holders of the Company’s securities before the transaction beneficially own less than 50% of the outstanding voting securities of the surviving entity after the transaction (based on their respective ownership interests as constituted
immediately prior to such transaction), or any sale, license, or other disposition of all or substantially all of the assets of the Company. 
 b. Treatment of Warrant at Acquisition. 
 (i) Upon the written request of
the Company, Holder agrees that, in the event of an Acquisition in which the sole consideration is cash and/or marketable securities, either (A) Holder shall exercise its conversion or purchase right under this Warrant and such exercise will be
deemed effective immediately prior to the consummation of such Acquisition or (B) if Holder elects not to exercise the Warrant, this Warrant will expire upon the consummation of such Acquisition. The Company shall provide the Holder with
written notice of its request relating to the foregoing (together with such reasonable information as the Holder may request in connection with such contemplated Acquisition giving rise to such notice), which is to be delivered to Holder not less
than ten (10) days prior to the closing of the proposed Acquisition. 
 (ii) Upon the written request of the Company,
Holder agrees that, in the event of an Acquisition that is an “arm’s-length” sale of all or substantially all of the Company’s assets (and only its assets) to a third party that is not an Affiliate (as defined below) of the
Company (a “True Asset Sale”), either (A) Holder shall exercise its conversion or purchase right under this Warrant and such exercise will be 

  
 3 

 
deemed effective immediately prior to the consummation of such Acquisition or (B) if Holder elects not to exercise the Warrant, this Warrant will continue until the Expiration Date if the
Company continues as a going concern following the closing of any such True Asset Sale. The Company shall provide the Holder with written notice of its request relating to the foregoing (together with such reasonable information as the Holder may
request in connection with such contemplated Acquisition giving rise to such notice), which is to be delivered to Holder not less than ten (10) days prior to the closing of the proposed Acquisition. 

(iii) Upon the written consent of the Company, Holder agrees that, in the event of a stock-for-stock Acquisition of the Company by a
publicly traded acquirer if, on the record date for the Acquisition, the fair market value of the Shares (or other securities issuable upon exercise of this Warrant) is equal to or greater than three times (3x) the Warrant Price, the Company
may require the Warrant to be deemed automatically exercised and the Holder shall participate in the Acquisition as a holder of the Shares (or other securities issuable upon exercise of the Warrant) on the same terms as other holders of the same
class of securities of the Company. 
 (iv) Upon the closing of any Acquisition other than those particularly described in
subsections (i), (ii) and (iii) above, the successor entity shall assume the obligations of this Warrant, and this Warrant shall be exercisable for the same securities, cash, and property as would be payable for the Shares issuable upon
exercise of the unexercised portion of this Warrant as if such Shares were outstanding on the record date for the Acquisition and its subsequent closing. The Warrant Price and/or number of Shares shall be adjusted accordingly. 

As used herein “Affiliate” shall mean any person or entity that owns or controls directly or indirectly ten
(10) percent or more of the stock of Company, any person or entity that controls or is controlled by or is under common control with such persons or entities, and each of such person’s or entity’s officers, directors, joint venturers
or partners, as applicable. 
 ARTICLE 2. ADJUSTMENTS TO THE SHARES. 

2.1 Stock Dividends, Splits, Etc. If the Company declares or pays a dividend on the shares of Series C Preferred payable in common
stock, or other securities, then upon exercise of this Warrant, for each Share acquired, Holder shall receive, without cost to Holder, the total number and kind of securities to which Holder would have been entitled had Holder owned the Shares of
record as of the date the dividend occurred. If the Company subdivides the shares of Series C Preferred by reclassification or otherwise into a greater number of shares or takes any other action which increase the amount of securities into which the
shares of Series C Preferred are convertible, the number of Shares purchasable hereunder shall be proportionately 

  
 4 

 
increased and the Warrant Price shall be proportionately decreased. If the outstanding shares of Series C Preferred are combined or consolidated, by reclassification or otherwise, into a lesser
number of shares, the Warrant Price shall be proportionately increased and the number of Shares shall be proportionately decreased. 
 2.2 Reclassification, Exchange, Combinations or Substitution. Upon any reclassification, exchange, substitution, or other event that results in a change of the number and/or class of the securities
issuable upon exercise or conversion of this Warrant, Holder shall be entitled to receive, upon exercise or conversion of this Warrant, the number and kind of securities and property that Holder would have received for the Shares if this Warrant had
been exercised immediately before such reclassification, exchange, substitution, or other event. Such an event shall include any automatic conversion of the outstanding or issuable securities of the Company of the same class or series as the Shares
to common stock pursuant to the terms of the Company’s Restated Certificate of Incorporation (the “Certificate”) upon the closing of a registered public offering of the Company’s common stock. The Company or its successor and
Holder shall promptly execute an amendment to this Warrant setting forth the number and kind of such new securities or other property issuable upon exercise or conversion of this Warrant as a result of such reclassification, exchange, substitution
or other event that results in a change of the number and/or class of securities issuable upon exercise or conversion of this Warrant. The amendment to this Warrant shall provide for adjustments which shall be as nearly equivalent as may be
practicable to the adjustments provided for in this Article 2 including, without limitation, adjustments to the Warrant Price and to the number of securities or property issuable upon exercise of the new Warrant. The provisions of this
Section 2.2 shall similarly apply to successive reclassifications, exchanges, substitutions, or other events. 
 2.3
Adjustments for Diluting Issuances. The Warrant Price and the number of shares of common stock issuable upon conversion of the Shares, shall be subject to adjustment, from time to time in the manner set forth in the Certificate as if the
Shares were issued and outstanding on and as of the date of any such required adjustment. The provisions set forth for the Shares in the Certificate relating to the above in effect as of the Issue Date may not be amended, modified or waived without
the prior written consent of Holder unless such amendment, modification or waiver affects the rights granted to Holder associated with the Shares in the same manner as such amendment, modification or waiver affects the rights associated with all
other shares of the same series and class as the Shares. 
 2.4 No Impairment. The Company shall not, by amendment of its
Certificate or through a reorganization, transfer of assets, consolidation, merger, dissolution, issue, or sale of securities or any other voluntary action, avoid or seek to avoid the observance or performance of any of the terms to be observed or
performed under this Warrant by the Company, but shall at all times in good faith assist in carrying out of all the provisions of this Article 2 and in taking all such action as may 

  
 5 

 
be necessary or appropriate to protect Holder’s rights under this Article 2 against impairment. The foregoing notwithstanding, the Company shall not have been deemed to have impaired
Holder’s rights hereunder if the Company amends its Certificate of Incorporation, or the holders of the Company’s preferred stock waive rights thereunder or elsewhere, in a manner that does not affect the Shares differently from the effect
that such amendments or waivers have generally on the rights, preferences, privileges or restrictions of the other shares of the same series of stock. 
 2.5 Fractional Shares. No fractional Shares shall be issuable upon exercise or conversion of the Warrant and the number of Shares to be issued shall be rounded down to the nearest whole Share. If a
fractional share interest arises upon any exercise or conversion of the Warrant, the Company shall eliminate such fractional share interest by paying Holder the amount computed by multiplying the fractional interest by the fair market value of a
full Share. 
 2.6 Certificate as to Adjustments. Upon each adjustment of the Warrant Price, the Company shall promptly
notify Holder in writing, and, at the Company’s expense, promptly compute such adjustment, and furnish Holder such adjustment and the facts upon which such adjustment is based. The Company shall, upon written request, furnish Holder a
certificate setting forth the Warrant Price in effect upon the date thereof and the series of adjustments leading to such Warrant Price. 

ARTICLE 3. REPRESENTATIONS AND COVENANTS OF THE COMPANY. 
 3.1 Representations and Warranties. The Company represents and warrants to Holder as follows: 
 (a) As of the Issue Date, the initial Warrant Price referenced on the first page of this Warrant is not greater than the price per share of the Series C Preferred at which such shares were last issued in
an arms-length transaction in which at least $500,000 of the Series C Preferred were sold. 
 (b) All Shares which may be issued
upon the exercise of the purchase right represented by this Warrant (including Shares issued to account for any adjustments made pursuant to Section 1.7 hereof), and all securities, if any, issuable upon conversion of the Shares, shall, upon
issuance, be duly authorized, validly issued, fully paid and nonassessable, and free of any liens and encumbrances except for restrictions on transfer provided for herein, under the Rights Agreement (as defined below) or under applicable federal and
state securities laws. 
 (c) The capitalization table attached hereto as Exhibit A completely and accurately reflects
the Company’s capitalization as of the Issue Date. 

  
 6 

 3.2 Notice of Certain Events. If the Company proposes at any time (a) to declare
any dividend or distribution upon any of the Shares, whether in cash, property, stock, or other securities and whether or not a regular cash dividend; (b) effect any reclassification or recapitalization of any of its Series C Preferred Stock;
(c) to consummate an Acquisition, or to liquidate, dissolve or wind up; or (d) offer holders of registration rights the opportunity to participate in an underwritten public offering of the Company’s securities for cash, then, in
connection with each such event, the Company shall give Holder: (1) at least 10 days prior written notice of the date on which a record will be taken for such dividend or distribution rights (and specifying the date on which the holders of
common stock will be entitled thereto) or for determining rights to vote, if any, in respect of the matters referred to in (a) above; (2) in the case of the matters referred to in (b) and (c) above at least 10 days prior written
notice of the date when the same will take place (and specifying the date on which the holders of common stock will be entitled to exchange their common stock for securities or other property deliverable upon the occurrence of such event); and (3)
in the case of the matter referred to in (d) above, the same notice as is given to the holders of such registration rights. The Company also agrees to provide information reasonably requested by Holder (at Holder’s cost) to enable Holder
to comply with Holder’s accounting or legal reporting requirements; provided that the Company shall not be obligated to provide information that is protected by attorney-client privilege. 

3.3 Registration Under The Act. The Company shall join the Holder as a party to the Company’s Investor Rights Agreement in
effect on the date hereof for the purposes of granting Holder certain S-3 and incidental, or “Piggyback.” registration rights with respect to the shares of common stock issuable upon the conversion of the Shares, and Holder agrees to be
bound by and subject to the terms and conditions of that certain Second Amended and Restated Investors’ Rights Agreement, as amended from time to time (the “Rights Agreement”), including the restrictions set forth in Section 1.15
thereof. 
 3.4 No Stockholder Rights. This Warrant does not entitle the holder hereof to any voting rights or other
rights as a stockholder of the Company prior to the exercise or conversion hereof. 
 ARTICLE 4. REPRESENTATIONS, WARRANTIES AND COVENANTS OF
HOLDER. 
 Holder represents, warrants, and covenants to the Company as follows: 

4.1 Purchase for Own Account. This Warrant and the securities to be acquired upon exercise of this Warrant (or upon conversion
thereof) by Holder (collectively, the “Securities”) will be acquired for investment for Holder’s account, not as a nominee or agent, and not with a view to the public resale or distribution within the meaning of the Act. Holder also
represents that Holder has not been formed for the specific purpose of acquiring the Securities. 

  
 7 

 4.2 Disclosure of Information. Holder has received or has had full access to all the
information it considers necessary or appropriate to make an informed investment decision with respect to the acquisition of this Warrant and the Securities. Holder further has had an opportunity to ask questions and receive answers from the Company
regarding the terms and conditions of the offering of this Warrant and the Securities and to obtain additional information (to the extent the Company possessed such information or could acquire it without unreasonable effort or expense) necessary to
verify any information furnished to Holder or to which Holder has access. 
 4.3 Investment Experience. Holder
understands that the purchase of this Warrant and the Securities involves substantial risk. Holder has experience as an investor in securities of companies in the development stage and acknowledges that Holder can bear the economic risk of such
Holder’s investment in this Warrant and the Securities and has such knowledge and experience in financial or business matters that Holder is capable of evaluating the merits and risks of its investment in this Warrant and the Securities and/or
has a preexisting personal or business relationship with the Company and certain of its officers, directors or controlling persons of a nature and duration that enables Holder to be aware of the character, business acumen and financial circumstances
of such persons. 
 4.4 Accredited Investor Status. Holder is an “accredited investor” within the meaning of
Regulation D promulgated under the Act. 
 4.5 The Act. Holder understands that this Warrant and the Shares issuable upon
exercise or conversion hereof have not been registered under the Act in reliance upon a specific exemption therefrom, which exemption depends upon, among other things, the bona fide nature of Holder’s investment intent as expressed herein.
Holder understands that this Warrant and the Shares issued upon any exercise or conversion hereof and any securities issued in connection therewith must be held indefinitely unless subsequently registered under the Act and qualified under applicable
state securities laws, or unless exemption from such registration and qualification are otherwise available. 
 4.6
Authorization. Holder represents that it has full power and authority to enter into this Warrant. This Warrant constitutes Holder’s valid and legally binding obligation, enforceable in accordance with its terms, except as may be limited
by (a) applicable bankruptcy, insolvency, reorganization or similar laws relating to or affecting the enforcement of creditors’ rights and (b) laws relating to the availability of specific performance, injunctive relief or other
equitable remedies. 
 ARTICLE 5. MISCELLANEOUS. 
 5.1 Term: This Warrant is exercisable in whole or in part at any time and from time to time on or before the earlier of (a) the Expiration Date or (b) as set froth in Article 1.6(b)
hereof. In addition, if the first Advance has not been made under the Loan Agreement at such time as the Revolving Line is no longer available to the Company, this Warrant shall expire. 

  
 8 

 5.2 Legends. This Warrant and the Shares (and the securities issuable, directly or
indirectly, upon conversion of the Shares, if any) shall be imprinted with a legend in substantially the following form: 
 THIS
WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AND PURSUANT TO THE PROVISIONS OF ARTICLE 5 BELOW, MAY NOT BE
OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAW OR, IN THE OPINION OF LEGAL COUNSEL IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER OF THESE SECURITIES,
SUCH OFFER, SALE OR TRANSFER, PLEDGE OR HYPOTHECATION IS EXEMPT FROM REGISTRATION. 
 THE SECURITIES REPRESENTED BY THIS
CERTIFICATE ARE SUBJECT TO A LOCK-UP PERIOD OF UP TO 180 DAYS (PLUS SUCH ADDITIONAL PERIOD AS MAY REASONABLY BE REQUESTED BY THE COMPANY OR SUCH UNDERWRITER TO ACCOMMODATE REGULATORY RESTRICTIONS ON (I) THE PUBLICATION OR OTHER DISTRIBUTION OF
RESEARCH REPORTS OR (II) ANALYST RECOMMENDATIONS AND OPINIONS, INCLUDING (WITHOUT LIMITATION) THE RESTRICTIONS SET FORTH IN RULE 2711(F)(4) OF THE NATIONAL ASSOCIATION OF SECURITIES DEALERS AND RULE 472(F)(4) OF THE NEW YORK STOCK EXCHANGE, AS
AMENDED, OR ANY SIMILAR SUCCESSOR RULES) AFTER THE EFFECTIVE DATE OF THE COMPANY’S REGISTRATION STATEMENT FILED UNDER THE ACT, AS AMENDED, AS SET FORTH IN AN AGREEMENT BETWEEN THE COMPANY AND THE ORIGINAL HOLDER OF THESE SECURITIES, A COPY OF
WHICH MAY BE OBTAINED AT THE COMPANY’S PRINCIPAL OFFICE. SUCH LOCK-UP PERIOD IS BINDING ON TRANSFEREES OF THESE SHARES. 

  
 9 

 5.3 Compliance with Securities Laws on Transfer. This Warrant and the Shares issuable
upon exercise of this Warrant (and the securities issuable, directly or indirectly, upon conversion of the Shares, if any) may not be transferred or assigned in whole or in part without compliance with applicable federal and state securities laws by
the transferor and the transferee (including, without limitation, the delivery of investment representation letters and legal opinions reasonably satisfactory to the Company, as reasonably requested by the Company) and any other contractual
restrictions between the Company and the Holder contained herein. The Company shall not require Holder to provide an opinion of counsel if the transfer is to Holder’s parent company, SVB Financial Group (formerly Silicon Valley Bancshares), or
any other affiliate of Holder. Additionally, the Company shall also not require an opinion of counsel if there is no material question as to the availability of current information as referenced in Rule 144(c), Holder represents that it has complied
with Rule 144(d) and (e) in reasonable detail, the selling broker represents that it has complied with Rule 144(f), and the Company is provided with a copy of Holder’s notice of proposed sale. 

5.4 Transfer Procedure. Upon receipt by Holder of the executed Warrant, Holder will transfer all of this Warrant to Holder’s
parent company, SVB Financial Group, by execution of an Assignment substantially in the form of Appendix 2. Subject to the provisions of Section 5.3, and upon providing Company with written notice, SVB Financial Group and any subsequent Holder
may transfer all or part of this Warrant or the Shares issuable upon exercise of this Warrant (or the Shares issuable directly or indirectly, upon conversion of the Shares, if any) to any transferee, provided, that, in connection with any such
transfer: (a) SVB Financial Group or any subsequent Holder provides the Company with notice of the portion of the Warrant being transferred, which notice shall include the name, address and taxpayer identification number of the transferee(s);
(b) transferee agrees to be bound by the terms and conditions of this Warrant and confirms the accuracy of the representations set forth in Article 4 hereof with respect to such transferee; and (c) Holder surrenders this Warrant to the
Company for reissuance to the transferee(s) (and Holder if applicable). The Company may refuse to transfer this Warrant or the Shares to any person who directly competes with the Company, unless, in either case, the stock of the Company is publicly
traded. 
 5.5 Notices. All notices and other communications from the Company to Holder, or vice versa, shall be deemed
delivered and effective when given personally or mailed by first-class registered or certified mail, postage prepaid (or on the first business day after transmission by facsimile), at such address as may have been furnished to the Company or Holder,
as the case may be, in writing by the Company or such holder from time to time. Effective upon receipt of the fully executed Warrant and the initial transfer described in Section 5.4 above, all notices to Holder shall be addressed as follows
until the Company receives notice of a change of address in connection with a transfer or otherwise: 

  
 10 

 SVB Financial Group 
 Attn: Treasury Department 
 3003 Tasman Drive, HA 200 

Santa Clara, California 95054 
 Telephone: (408) 654-7400 
 Facsimile: (408) 496-2405 

Notice to the Company shall be addressed as follows until Holder receives notice of a change in address: 

Guidewire Software, Inc. 
 Attn: Mike Shahbazian 
 2211 Bridgepointe Parkway, Suite 300 

San Mateo, California 04404 
 Facsimile: (650) 357-9101 
 E-mail: mshahbazian@guidewire.com 

5.6 Waiver. This Warrant and any other documents delivered pursuant to this Warrant constitute the full and entire understanding
and agreement between the parties with regard to the subjects hereof and thereof. This Warrant and any term hereof may be changed, waived, discharged or terminated only by the written consent of the Company and Holders; or if this Warrant has been
assigned in part, by the holders of the rights to purchase a majority of the Shares originally issuable pursuant to this Warrant. 
 5.7 Attorneys’ Fees. In the event of any dispute between the parties concerning the terms and provisions of this Warrant, the party prevailing in such dispute shall be entitled to collect from
the other party all costs incurred in such dispute, including reasonable attorneys’ fees. 
 5.8 Automatic Conversion
upon Expiration. In the event that, upon the Expiration Date, the fair market value of one Share (or other security issuable upon the exercise hereof) as determined in accordance with Section 1.3 above is greater than the Exercise Price in
effect on such date, then this Warrant shall automatically be deemed on and as of such date to be converted pursuant to Section 1.2 above as to all Shares (or such other securities) for which it shall not previously have been exercised or
converted, and the Company shall promptly deliver a certificate representing the Shares (or such other securities) issued upon such conversion to Holder. 
 5.9 Counterparts. This Warrant may be executed in counterparts, all of which together shall constitute one and the same agreement. 

  
 11 

 5.10 Governing Law. This Warrant shall be governed by and construed in accordance
with the laws of the State of California, without giving effect to its principles regarding conflicts of law. 
 [signature page
follows] 

  
 12 

 IN WITNESS
WHEREOF, the Company has caused this Warrant to be duly executed and delivered as of the Issue Date specified above. 
  

			
	“COMPANY”
	GUIDEWIRE SOFTWARE, INC.
		
	By:	 	/s/ Michael Shahbazian
	Name:	 	Michael Shahbazian
	Title:	 	CFO
	
	“HOLDER”
	SILICON VALLEY BANK
		
	By:	 	/s/ Tim Walsh
	Name:	 	Tim Walsh
	Title:	 	Senior Relationship Manager

 [Signature page to SVB Warrant under Revolver] 

 APPENDIX 1 
 NOTICE OF EXERCISE 
 1. Holder elects to purchase
                     shares of the Series C Preferred Stock of Guidewire, Inc. (the Company”) pursuant to the terms of the attached
Warrant, and tenders payment of the purchase price of the shares in full. 
 [or] 

1. Holder elects to convert the attached Warrant into Shares/cash [strike one] in the manner specified in the Warrant. 

[Strike paragraph that does not apply.] 
 2. Please issue a certificate or certificates representing the shares in the name specified below: 
  

	
	
	  
	 Holder’s Name

	
	 
	     

	 (Address)

 3. By its execution below and for the benefit of the Company, Holder hereby restates each of the
representations and warranties in Article 4 and each of its obligations pursuant to Sections 5.2, 5.3 and 5.4 of the Warrant as the date hereof. 
  

			
	HOLDER:
		
	By:	 	 
	Name:	 	 
	Title:	 	 
		
	(Date):	 	 

 APPENDIX 2 
 ASSIGNMENT FORM 
 (To assign the foregoing Warrant, execute this form and
supply the 
 required information. Do not use this form to purchase shares.) 

FOR VALUE RECEIVED, the foregoing Warrant and all rights evidenced thereby are hereby assigned to 

 

			
		 	SVB Financial Group
		
	whose address is:        	 	3003 Tasman Drive (HA-200)
		 	 Santa Clara, CA 95054

Tax ID:         91-1962278

Dated:                ,
20     
  

					
			
	Transferring Holder’s Signature:	  	 	  	
			
	Transferring Holder’s Address:	  	 	  	
		  	 	  	

 Signed in the presence of: 
  

 
 NOTE: The signature to this Assignment
Form set forth above must correspond with the name of the Holder as it appears on the face of the Warrant, without alteration or enlargement or any change whatever. Officers of corporations and those acting in a fiduciary or other representative
capacity should file proper evidence of authority to assign the foregoing Warrant. 
 In connection with the transfer of the Warrant to the
undersigned, the undersigned hereby agrees to be bound by and comply with all of the provisions and obligations applicable to the Holder contained in the Warrant and to execute any further documentation necessary to carry out the intent of the
foregoing agreement to be bound. 
 Transferee Holder’s Signature:
                                         
            
 Transferee Holder’s Name: (printed): SVB FINANCIAL GROUP

 Transferee Holder’s Address: 3003 Tasman Drive (HA-200) 
         Santa Clara, CA 95054

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00194-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00194-of-00352.parquet"}]]