Warrants to Purchase Shares of Preferred Stock



 Exhibit 10.29 
 THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE BEEN ACQUIRED FOR INVESTMENT AND NOT WITH A VIEW TO, OR IN CONNECTION WITH, THE SALE AND DISTRIBUTION THEREOF, AND HAVE NOT BEEN REGISTERED UNDER THE
SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”) OR ANY STATE SECURITIES LAWS. SUCH SECURITIES MAY NOT BE SOLD OR TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR AN OPINION OF COUNSEL IN A FORM REASONABLY ACCEPTABLE TO THE
COMPANY THAT SUCH REGISTRATION IS NOT REQUIRED DUE TO AN EXEMPTION THEREFROM UNDER SAID ACT AND ANY APPLICABLE STATE SECURITIES LAWS. 
 Date
of Issuance: May 30, 2008 
 WARRANT TO PURCHASE 
 SHARES OF PREFERRED STOCK OF 
 ENVIVIO, INC. 

Warrant No.      
 (Void after June 30, 2015) 
 This certifies that VENTURE LENDING & LEASING IV, LLC,
a Delaware limited liability company, or assigns (the “Holder”), for value received, is entitled to purchase from Envivio, Inc., a Delaware corporation (the “Company”), the Applicable Number (as hereinafter defined) of shares of
Preferred Stock (as hereinafter defined) at a per share price equal to the Stock Purchase Price (as hereinafter defined). The Holder may also exercise this Warrant on a cashless or “net issuance” basis as described in Section 1(b)
below. 
 This Warrant is being issued in connection with Supplement No. 2 to the Loan and Security Agreement dated as of
July 31, 2007 (as amended, restated and supplemented from time to time, the “Loan Agreement”) between the Company and Venture Lending & Leasing IV, Inc., an affiliate of Holder (“Lender”). Capitalized
terms used herein and not otherwise defined in this Warrant shall have the meaning(s) ascribed to them in the Loan Agreement unless the context would otherwise require. 
 The “Preferred Stock” shall be the Company’s Series F Preferred Stock; provided, however, that, within fourteen (14) days of receiving a notice from the Company
that the Company has consummated its Next Round (as hereinafter defined) (the “Election Notice”), the Holder may elect to have this Warrant be exercisable for the equity securities issued by the Company in the Next Round (the
“Next Round Securities”) by sending written notice of such to the Company, and in the event the Holder makes such election, the “Preferred Stock” shall thereafter be the Next Round Securities. The “Next
Round” means the next bona fide round of equity financing after the date hereof; provided that the Next Round excludes any additional closings of the Company’s Series F Preferred Stock. The Company shall provide an Election
Notice to the Holder as soon as reasonably practicable following consummation of the final closing of the Next Round and such Election Notice shall describe the material terms of the Next Round, including the terms of the Next Round Securities and
the consideration paid therefore and upon request by the Holder, and prior to the date for the election shall provide documentation regarding the foregoing. 
 The “Stock Purchase Price” shall be equal to $2.06 per share; provided, however, that if the Holder timely elects to have this Warrant become exercisable for Next Round
Securities as described in the foregoing paragraph, the “Stock Purchase Price” per share shall be the lowest price per share paid by an investor for the Company’s equity securities issued in the Next Round, including for this
purpose the value of all consideration given by an investor for such equity securities. 
 The “Applicable
Number” of shares purchasable hereunder shall be the number obtained by dividing (A) $225,000 by (B) the Stock Purchase Price. If in any case such number includes a fraction, the fraction shall be








 
adjusted to the closest lower integral number. If this Warrant has been partially exercised when the Holder makes the election to have this Warrant exercisable for Next Round Securities,
appropriate adjustment shall be made to the Applicable Number such that the same percentage of the Warrant’s face value is exercisable following such election as was exercisable prior to such election. 

As soon as reasonably practicable after the occurrence or non-occurrence of the latest event or condition necessary to fully determine
the Preferred Stock, the Stock Purchase Price and the Applicable Number, the Company shall execute and deliver a supplement to this Warrant in substantially the form of Exhibit “A” attached hereto, completed with such quantity and
price terms and other information as have been determined as a result of the occurrence or non-occurrence of such events or conditions. The provisions of such supplement, once completed and executed, shall control the interpretation and exercise of
this Warrant; provided, however, that the failure of the Company to deliver such supplement shall not affect the rights of the Holder of this Warrant to receive the Applicable Number of shares of Preferred Stock at the Stock Purchase Price as
set forth herein. 
 This Warrant may be exercised at any time or from time to time up to and including 5:00 p.m. (Pacific time)
on June 30, 2015 (the “Expiration Date”), upon surrender to the Company at its principal office at 400 Oyster Point Boulevard, Suite 325, South San Francisco, California 94080 (or at such other location as the Company may advise
Holder in writing) of this Warrant properly endorsed with the Form of Subscription attached hereto duly filled in and signed and upon payment in cash or by check of the aggregate Stock Purchase Price for the number of shares for which this Warrant
is being exercised determined in accordance with the provisions hereof. The Stock Purchase Price and the number of shares purchasable hereunder are subject to adjustment as provided in Section 4 of this Warrant. 

This Warrant is subject to the following terms and conditions: 

 

	 	1.	Exercise; Issuance of Certificates; Payment for Shares. 

 (a)            Unless an election is made pursuant to clause (b) of this Section 1, this Warrant shall be exercisable at the option of
the Holder, at any time or from time to time, on or before the Expiration Date for all or any portion of the shares of Preferred Stock (but not for a fraction of a share) which may be purchased hereunder for the Stock Purchase Price multiplied by
the number of shares to be purchased. In the event, however, that pursuant to the Company’s Certificate of Incorporation, as amended, an event causing automatic conversion of the Company’s Preferred Stock shall have occurred prior to the
exercise of this Warrant, in whole or in part, then this Warrant shall be exercisable for the number of shares of Common Stock of the Company into which the Preferred Stock not purchased upon any prior exercise of this Warrant would have been so
converted (and, where the context requires, reference to “Preferred Stock” shall be deemed to be or include such Common Stock, as may be appropriate). Except when there is an exercise of this Warrant pursuant to clause (b) of this
Section 1, payment shall be made by cash, wire transfer, check payable to the order of the Company or cancellation of indebtedness upon exercise. The Company agrees that the shares of Preferred Stock purchased under this Warrant shall be and
are deemed to be issued to the Holder hereof as the record owner of such shares as of the close of business on the date on which the form of subscription shall have been delivered and payment made for such shares. Subject to the provisions of
Section 2, certificates for the shares of Preferred Stock so purchased, together with any other securities or property to which the Holder hereof is entitled upon such exercise, shall be delivered to the Holder hereof by the Company at the
Company’s expense within a reasonable time after the rights represented by this Warrant have been so exercised. Except as provided in clause (b) of this Section 1, in case of a purchase of less than all the shares which may be
purchased under this Warrant, the Company shall cancel this Warrant and execute and deliver a new Warrant or Warrants of like tenor for the balance of the shares purchasable under this Warrant surrendered upon such purchase to the Holder hereof
within a reasonable time. Each stock certificate so delivered shall be in such denominations of Preferred Stock as may be requested by the Holder hereof and shall be registered in the name of such Holder or such other name as shall be designated by
such Holder, subject to the limitations contained in Section 2. 

(b)            The Holder, in lieu of exercising this Warrant by the cash
payment of the Stock Purchase Price pursuant to clause (a) of this Section 1, may elect, at any time on or before the Expiration Date, to surrender this Warrant and receive that number of shares of Preferred Stock equal to the quotient of:
(i) the difference between (A) the Per Share Price (as hereinafter defined) of the Preferred Stock, less (B) the Stock Purchase Price then in effect, multiplied by the number of shares of Preferred Stock the Holder would otherwise
have been entitled to 

  
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purchase hereunder pursuant to clause (a) of this Section 1 (or such lesser number of shares as the Holder may designate in the case of a partial exercise of this Warrant); over
(ii) the Per Share Price. Election to exercise under this section (b) may be made by delivering a signed form of subscription to the Company via facsimile, to be followed by delivery of this Warrant. 

(c)            For purposes of clause (b) of this Section 1,
“Per Share Price” means the product of: (i) the greater of (A) the closing price of the securities issuable upon conversion of the Preferred Stock, as quoted by NASDAQ or listed on any exchange, whichever is applicable, as
published in the Western Edition of The Wall Street Journal for the trading day immediately prior to the date of the Holder’s election hereunder or, (B) if applicable at the time of or in connection with the exercise under clause
(b) of this Section 1, the gross sales price of one share of the Company’s Common Stock pursuant to a registered public offering or that amount which stockholders of the Company will receive for each share of Common Stock pursuant to
a merger, reorganization or sale of assets; and (ii) that number of shares of Common Stock into which each share of Preferred Stock is convertible. If the securities issuable upon conversion of the Preferred Stock are not quoted by NASDAQ or
listed on an exchange and none of the above clauses apply, the Per Share Price of the Preferred Stock (or the equivalent number of shares of Common Stock into which such Preferred Stock is convertible) shall be the price per share which the Company
would obtain from a willing buyer for shares sold by the Company from authorized but unissued shares as such price shall be agreed upon by the Holder and the Company or, if agreement cannot be reached within ten (10) business days of the
Holder’s election hereunder, as such price shall be determined by a panel of three (3) appraisers, one (1) to be chosen by the Company, one (1) to be chosen by the Holder and the third to be chosen by the first two
(2) appraisers. If the appraisers cannot reach agreement within 30 days of the Holder’s election hereunder, then each appraiser shall deliver its appraisal and the appraisal which is neither the highest nor the lowest shall constitute the
Per Share Price. In the event either party fails to choose an appraiser within 30 days of the Holder’s election hereunder, then the appraisal of the sole appraiser shall constitute the Per Share Price. Each party shall bear the cost of the
appraiser selected by such party and the cost of the third appraiser shall be borne one-half by each party. In the event either party fails to choose an appraiser, the cost of the sole appraiser shall be borne one-half by each party. 

 

	 	2.	Limitation on Transfer. 


(a)            This Warrant and the Preferred Stock shall not be
transferable except upon the conditions specified in this Section 2, which conditions are intended to insure compliance with the provisions of the Securities Act. Each holder of this Warrant or the Preferred Stock issuable hereunder will cause
any proposed transferee of the Warrant or Preferred Stock to agree to take and hold such securities subject to the provisions and upon the conditions specified in this Section 2. This Warrant may not be sold, pledged, assigned, hypothecated,
gifted, transferred or disposed of in any manner either voluntarily or involuntarily by operation of law, other than by will or by the laws of descent or distribution without the prior written consent of the Company. Subject to the foregoing, the
terms of this Warrant shall be binding upon the executors, administrators, heirs, successors and assigns of the Holder. 

(b)            Each certificate representing (i) this Warrant,
(ii) the Preferred Stock, (iii) shares of the Company’s Common Stock issued upon conversion of the Preferred Stock and (iv) any other securities issued in respect to the Preferred Stock or Common Stock issued upon conversion of
the Preferred Stock upon any stock split, stock dividend, recapitalization, merger, consolidation or similar event, shall (unless otherwise permitted by the provisions of this Section 2 or unless such securities have been registered under the
Securities Act or sold under Rule 144) be stamped or otherwise imprinted with a legend substantially in the following form (in addition to any legend required under applicable state securities laws): 

THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE BEEN ACQUIRED FOR INVESTMENT AND NOT WITH A VIEW TO, OR IN CONNECTION WITH, THE SALE AND DISTRIBUTION
THEREOF, AND HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OR ANY STATE SECURITIES LAWS. SUCH SECURITIES MAY NOT BE SOLD OR TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR AN OPINION OF COUNSEL IN A FORM REASONABLY ACCEPTABLE TO THE COMPANY
THAT SUCH REGISTRATION IS NOT REQUIRED DUE TO AN EXEMPTION THEREFROM UNDER SAID ACT AND ANY APPLICABLE STATE SECURITIES LAWS. 

  
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 (c)            The Holder of
each certificate representing Preferred Stock issued upon conversion of the Preferred Stock agrees to comply in all respects with the provisions of this Section 2. Prior to any proposed transfer of any Preferred Stock unless there is in effect
a registration statement under the Securities Act covering the proposed transfer, the Holder thereof shall give written notice to the Company of such Holder’s intention to effect such transfer. Each such notice shall describe the manner and
circumstances of the proposed transfer in sufficient detail, and shall be accompanied (except in transactions in compliance with Rule 144) by either (i) a written opinion of legal counsel who shall be reasonably satisfactory to the Company
addressed to the Company and reasonably satisfactory in form and substance to the Company’s counsel, to the effect that the proposed transfer of the Preferred Stock may be effected without registration under the Securities Act, or (ii) a
“no action” letter from the Commission to the effect that the transfer of such securities without registration will not result in a recommendation by the staff of the Commission that action be taken with respect thereto, whereupon the
Holder of such Preferred Stock shall be entitled to transfer such Preferred Stock in accordance with the terms of the notice delivered by the Holder to the Company. 
 3.            Shares to be Fully Paid; Reservation of Shares. The Company covenants and agrees that all shares of Preferred Stock which
may be issued upon the exercise of the rights represented by this Warrant will, upon issuance, be duly authorized, validly issued, fully paid and nonassessable and free from all preemptive rights of any stockholder and free of all taxes, liens and
charges with respect to the issue thereof. The Company further covenants and agrees that during the period within which the rights represented by this Warrant may be exercised, the Company will at all times have authorized and reserved, for the
purpose of issue or transfer upon exercise of the subscription rights evidenced by this Warrant, a sufficient number of shares of authorized but unissued Preferred Stock, or other securities and property, when and as required to provide for the
exercise of the rights represented by this Warrant. The Company will take all such action as may be necessary to assure that such shares of Preferred Stock may be issued as provided herein without violation of any applicable law or regulation, or of
any requirements of any domestic securities exchange upon which the Preferred Stock may be listed. The Company will not take any action which would result in any adjustment of the Stock Purchase Price (as defined in Section 4 hereof)
(i) if the total number of shares of Preferred Stock issuable after such action upon exercise of all outstanding warrants, together with all shares of Preferred Stock then outstanding and all shares of Preferred Stock then issuable upon
exercise of all options and upon the conversion of all convertible securities then outstanding, would exceed the total number of shares of Preferred Stock then authorized by the Company’s Certificate of Incorporation, (ii) if the total
number of shares of Common Stock issuable after such action upon the conversion of all such shares of Preferred Stock together with all shares of Common Stock then outstanding and then issuable upon exercise of all options and upon the conversion of
all convertible securities then outstanding would exceed the total number of shares of Common Stock then authorized by the Company’s Certificate of Incorporation or (iii) if the par value per share of the Preferred Stock would exceed the
Stock Purchase Price. 
 4.            Adjustment of Stock
Purchase Price and Number of Shares. The Stock Purchase Price and the number of shares purchasable upon the exercise of this Warrant shall be subject to adjustment from time to time upon the occurrence of certain events described in this
Section 4. Upon each adjustment of the Stock Purchase Price, the Holder of this Warrant shall thereafter be entitled to purchase, at the Stock Purchase Price resulting from such adjustment, the number of shares obtained by multiplying the Stock
Purchase Price in effect immediately prior to such adjustment by the number of shares purchasable pursuant hereto immediately prior to such adjustment, and dividing the product thereof by the Stock Purchase Price resulting from such adjustment.

 4.1            Subdivision or Combination of Stock. In
case the Company shall at any time subdivide its outstanding shares of Preferred Stock into a greater number of shares, the Stock Purchase Price in effect immediately prior to such subdivision shall be proportionately reduced, and conversely, in
case the outstanding shares of Preferred Stock of the Company shall be combined into a smaller number of shares, the Stock Purchase Price in effect immediately prior to such combination shall be proportionately increased. 

4.2            Dividends in Preferred Stock, Other Stock, Property,
Reclassification. If at any time or from time to time the holders of Preferred Stock (or any shares of stock or other securities at the time receivable upon the exercise of this Warrant) shall have received or become entitled to receive, without
payment therefor, 

  
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 (a)            Preferred Stock,
or any shares of stock or other securities whether or not such securities are at any time directly or indirectly convertible into or exchangeable for Preferred Stock, or any rights or options to subscribe for, purchase or otherwise acquire any of
the foregoing by way of dividend or other distribution, or 

(b)            any cash paid or payable otherwise than as a cash dividend,
or 
 (c)            Preferred Stock or other or additional stock
or other securities or property (including cash) by way of spin off, split-up, reclassification, combination of shares or similar corporate rearrangement, (other than shares of Preferred Stock issued as a stock split, adjustments in respect of which
shall be covered by the terms of Section 4.1 above), 
 Then and in each such case, the Holder hereof shall, upon the exercise of this
Warrant, be entitled to receive, in addition to the number of shares of Preferred Stock receivable thereupon, and without payment of any additional consideration therefore, the amount of stock and other securities and property (including cash in the
cases referred to in clauses (b) and (c) above) which such Holder would hold on the date of such exercise had he been the holder of record of such Preferred Stock as of the date on which holders of Preferred Stock received or became
entitled to receive such shares and/or all other additional stock and other securities and property. 

4.3            Reorganization, Reclassification, Consolidation, Merger or
Sale. If any capital reorganization of the capital stock of the Company, or any consolidation or merger of the Company with another corporation, or the sale of all or substantially all of its assets to another corporation shall be effected in
such a way that holders of Preferred Stock shall be entitled to receive stock, securities or assets with respect to or in exchange for Preferred Stock, then, as a condition of such reorganization, reclassification, consolidation, merger or sale,
lawful and adequate provisions shall be made whereby the holder hereof shall thereafter have the right to purchase and receive (in lieu of the shares of the Preferred Stock of the Company immediately theretofore purchasable and receivable upon the
exercise of the rights represented hereby) such shares of stock, securities or assets as may be issued or payable with respect to or in exchange for a number of outstanding shares of such Preferred Stock equal to the number of shares of such stock
immediately theretofore purchasable and receivable upon the exercise of the rights represented hereby. In any such case, appropriate provision shall be made with respect to the rights and interests of the holder of this Warrant to the end that the
provisions hereof (including, without limitation, provisions for adjustments of the Stock Purchase Price and of the number of shares purchasable and receivable upon the exercise of this Warrant) shall thereafter be applicable, as nearly as may be
possible, in relation to any shares of stock, securities or assets thereafter deliverable upon the exercise hereof. The Company will not effect any such consolidation, merger or sale unless, prior to the consummation thereof, the successor
corporation (if other than the Company) resulting from such consolidation or the corporation purchasing such assets shall assume by written instrument, executed and mailed or delivered to the registered Holder hereof at the last address of such
Holder appearing on the books of the Company, the obligation to deliver to such Holder such shares of stock, securities or assets as, in accordance with the foregoing provisions, such Holder may be entitled to purchase. 

4.4            Sale or Issuance Below Purchase Price. The other
antidilution rights applicable to the shares of series Preferred Stock purchasable hereunder are set forth in the Company’s Certificate of Incorporation, as amended through the date hereof (the “Charter”). The Company shall promptly
provide the Holder hereof with any restatement, amendment, modification or waiver of the Charter promptly after the same has been made. 
 4.5            Notice of Adjustment. Upon any adjustment of the Stock Purchase Price, and/or any increase or decrease in the number of
shares purchasable upon the exercise of this Warrant the Company shall give written notice thereof, by first class mail, postage prepaid, addressed to the registered holder of this Warrant at the address of such holder as shown on the books of the
Company. The notice, which may be substantially in the form of Exhibit “A” attached hereto, shall be signed by the Company’s chief financial officer and shall state the Stock Purchase Price resulting from such adjustment and the
increase or decrease, if any, in the number of shares purchasable at such price upon the exercise of this Warrant, setting forth in reasonable detail the method of calculation and the facts upon which such calculation is based. 

  
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 4.6            Other
Notices. If at any time: 
 (a)            the Company shall
declare any cash dividend upon its Preferred Stock; 

(b)            the Company shall declare any dividend upon its Preferred
Stock payable in stock or make any special dividend or other distribution to the holders of its Preferred Stock; 

(c)            there shall be any capital reorganization or reclassification
of the capital stock of the Company, or consolidation or merger of the Company with, or sale of all or substantially all of its assets to, another entity; 
 (d)            there shall be a voluntary or involuntary dissolution, liquidation or winding-up of the Company; or 

(e)            the Company shall take or propose to take any other action,
notice of which is actually provided to holders of the Preferred Stock; 
 then, in any one or more of said cases, the Company shall give, by
first class mail, postage prepaid, addressed to the Holder of this Warrant at the address of such Holder as shown on the books of the Company, (i) at least 10 day’s prior written notice of the date on which the books of the Company shall
close or a record shall be taken for such dividend, distribution or subscription rights or for determining rights to vote in respect of any such reorganization, reclassification, consolidation, merger, sale, dissolution, liquidation or winding-up,
or other action and (ii) in the case of any such reorganization, reclassification, consolidation, merger, sale, dissolution, liquidation or winding-up, or other action, at least 20 day’s written notice of the date when the same shall take
place. Any notice given in accordance with the foregoing clause (i) shall also specify, in the case of any such dividend, distribution or subscription rights, the date on which the holders of Preferred Stock shall be entitled thereto. Any
notice given in accordance with the foregoing clause (ii) shall also specify the date on which the holders of Preferred Stock shall be entitled to exchange their Preferred Stock for securities or other property deliverable upon such
reorganization, reclassification, consolidation, merger, sale, dissolution, liquidation or winding-up, or other action as the case may be. 
 4.7            Certain Events. If any change in the outstanding Preferred Stock of the Company or any other event occurs as to which the
other provisions of this Section 4 are not strictly applicable or if strictly applicable would not fairly effect the adjustments to this Warrant in accordance with the essential intent and principles of such provisions, then the Board of
Directors of the Company shall make in good faith an adjustment in the number and class of shares issuable under this Warrant, the Stock Purchase Price and/or the application of such provisions, in accordance with such essential intent and
principles, so as to protect such purchase rights as aforesaid. The adjustment shall be such as will give the Holder of this Warrant upon exercise for the same aggregate Stock Purchase Price the total number, class and kind of shares as the Holder
would have owned had this Warrant been exercised prior to the event and had the Holder continued to hold such shares until after the event requiring adjustment. 
 5.            Issue Tax. The issuance of certificates for shares of Preferred Stock upon the exercise of this Warrant shall be made
without charge to the Holder of this Warrant for any issue tax in respect thereof; provided, however, that the Company shall not be required to pay any tax which may be payable in respect of any transfer involved in the issuance and delivery of any
certificate in a name other than that of the then Holder of this Warrant being exercised. 

6.            Closing of Books. The Company will at no time close its
transfer books against the transfer of this Warrant or of any shares of Preferred Stock issued or issuable upon the exercise of this Warrant in any manner which interferes with the timely exercise of this Warrant. 

7.            No Voting or Dividend Rights; Limitation of Liability.
Nothing contained in this Warrant shall be construed as conferring upon the Holder hereof the right to vote or to consent as a stockholder in respect of meetings of stockholders for the election of directors of the Company or any other matters or
any rights whatsoever as a stockholder of the Company. No dividends or interest shall be payable or accrued in respect of this Warrant or the interest represented hereby or the shares purchasable hereunder until, and only to the extent that, this
Warrant shall 

  
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have been exercised. No provisions hereof, in the absence of affirmative action by the Holder to purchase shares of Preferred Stock, and no mere enumeration herein of the rights or privileges of
the Holder hereof, shall give rise to any liability of such Holder for the Stock Purchase Price or as a stockholder of the Company, whether such liability is asserted by the Company or by its creditors. 

8.            Registration Rights. The Holder hereof shall be
entitled, with respect to the shares of Preferred Stock issued upon exercise hereof or the shares of Common Stock or other securities issued upon conversion of such Preferred Stock as the case may be, to all of the registration rights set forth in
the Amended and Restated Investors Rights Agreement dated as of January 19,2007 (the “Rights Agreement”), as amended to date, to the same extent and on the same terms and conditions as possessed by the investors thereunder with the
following exceptions and clarifications: (i) the Holder will have no demand registration rights; (ii) the Holder will be subject to the same provisions regarding indemnification as contained in the Rights Agreement; and (iii) the
registration rights are freely assignable by the Holder of this Warrant in connection with a permitted transfer of this Warrant or the shares issuable upon exercise hereof. The Company shall take such action as may be reasonably necessary to assure
that the granting of such registration rights to the Holder does not violate the provisions of the Rights Agreement or any of the Company’s charter documents or rights of prior grantees of registration rights. 

9.            Rights and Obligations Survive Exercise of Warrant. The
rights and obligations of the Company, of the Holder of this Warrant and of the holder of shares of Preferred Stock issued upon exercise of this Warrant, contained in Sections 6 and 8 shall survive the exercise of this Warrant. 

 

10.          Modification and Waiver. This Warrant and any provision hereof may
be changed, waived, discharged or terminated only by an instrument in writing signed by the party against which enforcement of the same is sought. 
  

11.          Notices. Any notice, request or other document required or
permitted to be given or delivered to the Holder hereof or the Company shall be deemed to have been given (i) upon receipt if delivered personally or by courier (ii) upon confirmation of receipt if by telecopy or (iii) three business
days after deposit in the US mail, with postage prepaid and certified or registered, to each such Holder at its address as shown on the books of the Company or to the Company at the address indicated therefor in the first paragraph of this Warrant.

  

12.          Binding Effect on Successors. This Warrant shall be binding upon
any corporation succeeding the Company by merger, consolidation or acquisition of all or substantially all of the Company’s assets. All of the obligations of the Company relating to the Preferred Stock issuable upon the exercise of this Warrant
shall survive the exercise and termination of this Warrant. All of the covenants and agreements of the Company shall inure to the benefit of the successors and assign of the holder hereof. The Company will, at the time of the exercise of this
Warrant, in whole or in part, upon request of the Holder hereof but at the Company’s expense, acknowledge in writing its continuing obligation to the Holder hereof in respect of any rights (including, without limitation, any right to
registration of the shares of Common Stock) to which the holder hereof shall continue to be entitled after such exercise in accordance with this Warrant; provided, that the failure of the holder hereof to make any such request shall not affect the
continuing obligation of the Company to the Holder hereof in respect of such rights. 

13.          Descriptive Headings and Governing Law. The descriptive headings of
the several sections and paragraphs of this Warrant are inserted for convenience only and do not constitute a part of this Warrant. This Warrant shall be construed and enforced in accordance with, and the rights of the parties shall be governed by,
the laws of the State of California. 
  

14.          Lost Warrants or Stock Certificates. The Company represents and
warrants to the Holder hereof that upon receipt of evidence reasonably satisfactory to the Company of the loss, theft, destruction, or mutilation of any Warrant or stock certificate and, in the case of any such loss, theft or destruction, upon
receipt of an indemnity reasonably satisfactory to the Company, or in the case of any such mutilation upon surrender and cancellation of such Warrant or stock certificate, the Company at its expense will make and deliver a new Warrant or stock
certificate, of like tenor, in lieu of the lost, stolen, destroyed or mutilated Warrant or stock certificate. 

  
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 15.          Fractional Shares. No
fractional shares shall be issued upon exercise of this Warrant. The Company shall, in lieu of issuing any fractional share, pay the holder entitled to such fraction a sum in cash equal to such fraction multiplied by the then effective Stock
Purchase Price. 
 16.          Representations of Holder. With respect
to this Warrant, Holder represents and warrants to the Company as follows: 

16.1        Experience. It is experienced in evaluating and investing in companies
engaged in businesses similar to that of the Company; it understands that investment in this Warrant involves substantial risks; it has made detailed inquiries concerning the Company, its business and services, its officers and its personnel; the
officers of the Company have made available to Holder any and all written information it has requested; the officers of the Company have answered to Holder’s satisfaction all inquiries made by it; in making this investment it has relied upon
information made available to it by the Company; and it has such knowledge and experience in financial and business matters that it is capable of evaluating the merits and risks of investment in the Company and it is able to bear the economic risk
of that investment. 
 16.2        Investment. It is acquiring this Warrant for
investment for its own account and not with a view to, or for resale in connection with, any distribution thereof. It understands that this Warrant, the shares of Preferred Stock issuable upon exercise thereof and the shares of Common Stock issuable
upon conversion of the Preferred Stock, have not been registered under the Securities Act, nor qualified under applicable state securities laws. Holder is an “accredited investor” within the meaning of Securities and Exchange Commission
(“SEC”) Rule 501 of Regulation D, as presently in effect, and will execute any investment representation statement requested by the Company. 
 16.3        Rule 144. It acknowledges that this Warrant, the Preferred Stock and the Common Stock must be held indefinitely unless they are subsequently
registered under the Securities Act or an exemption from such registration is available. It has been advised or is aware of the provisions of Rule 144 promulgated under the Securities Act. 

16.4        Access to Data. It has had an opportunity to discuss the Company’s
business, management and financial affairs with the Company’s management and has had the opportunity to inspect the Company’s facilities. 
 17.          Additional Representations and Covenants of the Company. The Company hereby represents, warrants and agrees as follows: 

17.1        Corporate Power. The Company has all requisite corporate power and corporate
authority to issue this Warrant and to carry out and perform its obligations hereunder. 

17.2        Authorization. All corporate action on the part of the Company, its directors
and stockholders necessary for the authorization, execution, delivery and performance by the Company of this has been taken. This Warrant is a valid and binding obligation of the Company, enforceable in accordance with its terms. 

17.3        Offering. Subject in part to the truth and accuracy of Holder’s
representations set forth in Section 16 hereof, the offer, issuance and sale of this Warrant is, and the issuance of Preferred Stock upon exercise of this Warrant and the issuance of Common Stock upon conversion of the Preferred Stock will be
exempt from the registration requirements of the Securities Act, and are exempt from the qualification requirements of any applicable state securities laws; and neither the Company nor anyone acting on its behalf will take any action hereafter that
would cause the loss of such exemptions. 
 17.4        Stock Issuance. Upon
exercise of this Warrant, the Company will use its best efforts to cause stock certificates representing the shares of Preferred Stock purchased pursuant to the exercise to be issued in the names of Holder, its nominees or assignees, as appropriate
at the time of such exercise. Upon conversion of the shares of Preferred Stock into shares of Common Stock, the Company will issue the Common Stock in the names of Holder, its nominees or assignees, as appropriate. 

  
 8 








 17.5            Certificates
and By-Laws.  The Company has provided Holder with true and complete copies of the Company’s Certificate of Incorporation, By-Laws, and each Certificate of Designation or other charter document setting, forth any rights,
preferences and privileges of Company’s capital stock, each as amended and in effect on the date of issuance of this Warrant. 
 17.6            Conversion of Preferred Stock.  As of the date hereof, each share of the Preferred Stock is convertible into
one share of the Common Stock. 
 17.7            Financial and
Other Reports.  From time to time up to the earlier of the Expiration Date or the complete exercise of this Warrant, the Company shall furnish to Holder (i) within 90 days after the close of each fiscal year of the Company an
audited balance sheet and statement of changes in financial position at and as of the end of such fiscal year, together with an audited statement of income for such fiscal year; (ii) within 45 days after the close of each fiscal quarter of the
Company, an unaudited balance sheet and statement of cash flows at and as of the end of such quarter, together with an unaudited statement of income for such quarter; and (iii) promptly after sending, making available, or filing, copies of all
reports, proxy statements, and financial statements that the Company sends or makes available to its stockholders and all registration statements and reports that the Company files with the SEC or any other governmental or regulatory authority.

  
 IN WITNESS WHEREOF, Company has caused this Warrant to be duly executed
by its officer, thereunto duly authorized as of the date of issuance set forth on the first page hereof. 
 ENVIVIO, INC 

 
  

			
	 By:
	 	 /s/ Albert Liong

		
	 Title:
	 	 CFO



  
 9 








 FORM OF SUBSCRIPTION 
 (To be signed only upon exercise of Warrant) 
  

	To:	ENVIVIO, INC. 

  

	 ̈	The undersigned, the holder of the within Warrant, hereby irrevocably elects to exercise the purchase right represented by such Warrant for, and to purchase thereunder,
(1) See Below                     
(                )shares (the “Shares”) of Stock of
                     and herewith makes payment of
                     Dollars ($            ) therefor, and requests
that the certificates for such shares be issued in the name of, and delivered to,         , whose address is
                    . 

  

 

	 ̈	The undersigned hereby elects to convert      percent (    %) of the value of the Warrant pursuant to the
provisions of Section 1(b) of the Warrant. 

 The undersigned acknowledges that it has reviewed the representations and
warranties contained in Section 17 of this Warrant and by its signature below hereby makes such representations and warranties to the Company. 
  

 

							
		 	Dated	  	  
	  	
				
		 	Holder:	  	  
	  	
				
		 	By:	  	  
	  	
				
		 	Its:	  	  
	  	
			
		 	(Address)	  	
			
		 	                           
                                         
        	  	
			
		 	                           
                                         
        	  	

  

	(1)	Insert here the number of shares called for on the face of the Warrant (or, in the case of a partial exercise, the portion thereof as to which the Warrant is being
exercised), in either case without making any adjustment for additional Preferred Stock or any other stock or other securities or property or cash which, pursuant to the adjustment provisions of the Warrant, may be issuable upon exercise.









 ASSIGNMENT 
 FOR VALUE RECEIVED, the undersigned, the holder of the within Warrant, hereby sells, assigns and transfers all of the rights of the undersigned under the within Warrant, with respect to the number of
shares of Preferred Stock covered thereby set forth herein below, unto: 
  
  

					
	Name of Assignee	  	Address	  	No. of Shares
	  

		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	

  

					
		 	Dated	  	  

			
		 	Holder:	  	  

			
		 	By:	  	  

			
		 	Its:	  	  









 EXHIBIT “A” 

[On letterhead of the Company] 
 Reference is hereby made to that certain Warrant dated May     , 2008 issued by ENVIVIO, INC, a Delaware corporation (the “Company”), to VENTURE LENDING &
LEASING IV, INC., a Maryland corporation (the “Holder”). 
 [IF APPLICABLE] The Warrant provides that the actual
number of shares of the Company’s capital stock issuable upon exercise of the Warrant and the initial exercise price per share are to be determined by reference to one or more events or conditions subsequent to the issuance of the Warrant. Such
events or conditions have now occurred or lapsed, and the Company wishes to confirm the actual number of shares issuable and the initial exercise price. The provisions of this Supplement to Warrant are incorporated into the Warrant by this
reference, and shall control the interpretation and exercise of the Warrant. 
 [IF APPLICABLE] Notice is hereby given pursuant
to Section 4.5 of the Warrant that the following adjustment(s) have been made to the Warrant: [describe adjustments, setting forth details regarding method of calculation and facts upon which calculation is based]. 

This certifies that the Holder is entitled to purchase from the Company
                            
(                    ) fully paid and nonassessable shares of the Company’s
             Stock at a price of              Dollars
($            ) per share (the “Stock Purchase Price”). The Stock Purchase Price and the number of shares purchasable under the Warrant remain subject to adjustment as
provided in Section 4 of the Warrant. 
 Executed this      day of
            , 200    . 
  

					
	ENVIVIO, INC	 	
			
	By:	 	  
	 	
			
	Name:	 	  
	 	
			
	Title:	 	  
	 	









 THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE BEEN ACQUIRED FOR INVESTMENT AND NOT WITH A VIEW TO, OR
IN CONNECTION WITH, THE SALE AND DISTRIBUTION THEREOF, AND HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”) OR ANY STATE SECURITIES LAWS. SUCH SECURITIES MAY NOT BE SOLD OR TRANSFERRED IN THE
ABSENCE OF SUCH REGISTRATION OR AN OPINION OF COUNSEL IN A FORM REASONABLY ACCEPTABLE TO THE COMPANY THAT SUCH REGISTRATION IS NOT REQUIRED DUE TO AN EXEMPTION THEREFROM UNDER SAID ACT AND ANY APPLICABLE STATE SECURITIES LAWS. 

 
 Date of Issuance: May 30, 2008 

 
 WARRANT TO PURCHASE 

SHARES OF PREFERRED STOCK OF 
 ENVIVIO, INC. 
 Warrant No.      

(Void after June 30, 2015) 

This certifies that VENTURE LENDING & LEASING V, LLC, a Delaware limited liability company, or assigns (the “Holder”), for value
received, is entitled to purchase from Envivio, Inc., a Delaware corporation (the “Company”), the Applicable Number (as hereinafter defined) of shares of Preferred Stock (as hereinafter defined) at a per share price equal to the Stock
Purchase Price (as hereinafter defined). The Holder may also exercise this Warrant on a cashless or “net issuance” basis as described in Section 1(b) below. 
 This Warrant is being issued in connection with Supplement No. 2 to the Loan and Security Agreement dated as of July 31, 2007 (as amended, restated and supplemented from time to time, the
“Loan Agreement”) between the Company and Venture Lending & Leasing V, Inc., an affiliate of Holder (“Lender”). Capitalized terms used herein and not otherwise defined in this Warrant shall have the
meaning(s) ascribed to them in the Loan Agreement unless the context would otherwise require. 
 The “Preferred
Stock” shall be the Company’s Series F Preferred Stock; provided, however, that, within fourteen (14) days of receiving a notice from the Company that the Company has consummated its Next Round (as hereinafter
defined) (the “Election Notice”), the Holder may elect to have this Warrant be exercisable for the equity securities issued by the Company in the Next Round (the “Next Round Securities”) by sending written notice of
such to the Company, and in the event the Holder makes such election, the “Preferred Stock” shall thereafter be the Next Round Securities. The “Next Round” means the next bona fide round of equity financing after
the date hereof; provided that the Next Round excludes any additional closings of the Company’s Series F Preferred Stock. The Company shall provide an Election Notice to the Holder as soon as reasonably practicable following consummation
of the final closing of the Next Round and such Election Notice shall describe the material terms of the Next Round, including the terms of the Next Round Securities and the consideration paid therefore and upon request by the Holder, and prior to
the date for the election shall provide documentation regarding the foregoing. 
 The “Stock Purchase Price”
shall be equal to $2.06 per share; provided, however, that if the Holder timely elects to have this Warrant become exercisable for Next Round Securities as described in the foregoing paragraph, the “Stock Purchase
Price” per share shall be the lowest price per share paid by an investor for the Company’s equity securities issued in the Next Round, including for this purpose the value of all consideration given by an investor for such equity
securities. 
 The “Applicable Number” of shares purchasable hereunder shall be the number obtained by dividing
(A) $225,000 by (B) the Stock Purchase Price. If in any case such number includes a fraction, the fraction shall be 







 
adjusted to the closest lower integral number. If this Warrant has been partially exercised when the Holder makes the election to have this Warrant exercisable for Next Round Securities,
appropriate adjustment shall be made to the Applicable Number such that the same percentage of the Warrant’s face value is exercisable following such election as was exercisable prior to such election. 

As soon as reasonably practicable after the occurrence or non-occurrence of the latest event or condition necessary to fully determine
the Preferred Stock, the Stock Purchase Price and the Applicable Number, the Company shall execute and deliver a supplement to this Warrant in substantially the form of Exhibit “A” attached hereto, completed with such quantity and
price terms and other information as have been determined as a result of the occurrence or non-occurrence of such events or conditions. The provisions of such supplement, once completed and executed, shall control the interpretation and exercise of
this Warrant; provided, however, that the failure of the Company to deliver such supplement shall not affect the rights of the Holder of this Warrant to receive the Applicable Number of shares of Preferred Stock at the Stock Purchase Price as
set forth herein. 
 This Warrant may be exercised at any time or from time to time up to and including 5:00 p.m. (Pacific time)
on June 30, 2015 (the “Expiration Date”), upon surrender to the Company at its principal office at 400 Oyster Point Boulevard, Suite 325, South San Francisco, California 94080 (or at such other location as the Company may advise
Holder in writing) of this Warrant properly endorsed with the Form of Subscription attached hereto duly filled in and signed and upon payment in cash or by check of the aggregate Stock Purchase Price for the number of shares for which this Warrant
is being exercised determined in accordance with the provisions hereof. The Stock Purchase Price and the number of shares purchasable hereunder are subject to adjustment as provided in Section 4 of this Warrant. 

This Warrant is subject to the following terms and conditions: 

 

	 	1.	Exercise; Issuance of Certificates; Payment for Shares. 

 (a)            Unless an election is made pursuant to clause (b) of this Section 1, this Warrant shall be exercisable at the option of
the Holder, at any time or from time to time, on or before the Expiration Date for all or any portion of the shares of Preferred Stock (but not for a fraction of a share) which may be purchased hereunder for the Stock Purchase Price multiplied by
the number of shares to be purchased. In the event, however, that pursuant to the Company’s Certificate of Incorporation, as amended, an event causing automatic conversion of the Company’s Preferred Stock shall have occurred prior to the
exercise of this Warrant, in whole or in part, then this Warrant shall be exercisable for the number of shares of Common Stock of the Company into which the Preferred Stock not purchased upon any prior exercise of this Warrant would have been so
converted (and, where the context requires, reference to “Preferred Stock” shall be deemed to be or include such Common Stock, as may be appropriate). Except when there is an exercise of this Warrant pursuant to clause (b) of this
Section 1, payment shall be made by cash, wire transfer, check payable to the order of the Company or cancellation of indebtedness upon exercise. The Company agrees that the shares of Preferred Stock purchased under this Warrant shall be and
are deemed to be issued to the Holder hereof as the record owner of such shares as of the close of business on the date on which the form of subscription shall have been delivered and payment made for such shares. Subject to the provisions of
Section 2, certificates for the shares of Preferred Stock so purchased, together with any other securities or property to which the Holder hereof is entitled upon such exercise, shall be delivered to the Holder hereof by the Company at the
Company’s expense within a reasonable time after the rights represented by this Warrant have been so exercised. Except as provided in clause (b) of this Section 1, in case of a purchase of less than all the shares which may be
purchased under this Warrant, the Company shall cancel this Warrant and execute and deliver a new Warrant or Warrants of like tenor for the balance of the shares purchasable under this Warrant surrendered upon such purchase to the Holder hereof
within a reasonable time. Each stock certificate so delivered shall be in such denominations of Preferred Stock as may be requested by the Holder hereof and shall be registered in the name of such Holder or such other name as shall be designated by
such Holder, subject to the limitations contained in Section 2. 

(b)            The Holder, in lieu of exercising this Warrant by the cash
payment of the Stock Purchase Price pursuant to clause (a) of this Section 1, may elect, at any time on or before the Expiration Date, to surrender this Warrant and receive that number of shares of Preferred Stock equal to the quotient of:
(i) the difference between (A) the Per Share Price (as hereinafter defined) of the Preferred Stock, less (B) the Stock Purchase Price then in effect, multiplied by the number of shares of Preferred Stock the Holder would otherwise
have been entitled to 

  
 2 








 
purchase hereunder pursuant to clause (a) of this Section 1 (or such lesser number of shares as the Holder may designate in the case of a partial exercise of this Warrant); over
(ii) the Per Share Price. Election to exercise under this section (b) may be made by delivering a signed form of subscription to the Company via facsimile, to be followed by delivery of this Warrant. 

(c)            For purposes of clause (b) of this Section 1,
“Per Share Price” means the product of: (i) the greater of (A) the closing price of the securities issuable upon conversion of the Preferred Stock, as quoted by NASDAQ or listed on any exchange, whichever is applicable, as
published in the Western Edition of The Wall Street Journal for the trading day immediately prior to the date of the Holder’s election hereunder or, (B) if applicable at the time of or in connection with the exercise under clause
(b) of this Section 1, the gross sales price of one share of the Company’s Common Stock pursuant to a registered public offering or that amount which stockholders of the Company will receive for each share of Common Stock pursuant to
a merger, reorganization or sale of assets; and (ii) that number of shares of Common Stock into which each share of Preferred Stock is convertible. If the securities issuable upon conversion of the Preferred Stock are not quoted by NASDAQ or
listed on an exchange and none of the above clauses apply, the Per Share Price of the Preferred Stock (or the equivalent number of shares of Common Stock into which such Preferred Stock is convertible) shall be the price per share which the Company
would obtain from a willing buyer for shares sold by the Company from authorized but unissued shares as such price shall be agreed upon by the Holder and the Company or, if agreement cannot be reached within ten (10) business days of the
Holder’s election hereunder, as such price shall be determined by a panel of three (3) appraisers, one (1) to be chosen by the Company, one (1) to be chosen by the Holder and the third to be chosen by the first two
(2) appraisers. If the appraisers cannot reach agreement within 30 days of the Holder’s election hereunder, then each appraiser shall deliver its appraisal and the appraisal which is neither the highest nor the lowest shall constitute the
Per Share Price. In the event either party fails to choose an appraiser within 30 days of the Holder’s election hereunder, then the appraisal of the sole appraiser shall constitute the Per Share Price. Each party shall bear the cost of the
appraiser selected by such party and the cost of the third appraiser shall be borne one-half by each party. In the event either party fails to choose an appraiser, the cost of the sole appraiser shall be borne one-half by each party. 

 

	 	2.	Limitation on Transfer. 


(a)            This Warrant and the Preferred Stock shall not be
transferable except upon the conditions specified in this Section 2, which conditions are intended to insure compliance with the provisions of the Securities Act. Each holder of this Warrant or the Preferred Stock issuable hereunder will cause
any proposed transferee of the Warrant or Preferred Stock to agree to take and hold such securities subject to the provisions and upon the conditions specified in this Section 2. This Warrant may not be sold, pledged, assigned, hypothecated,
gifted, transferred or disposed of in any manner either voluntarily or involuntarily by operation of law, other than by will or by the laws of descent or distribution without the prior written consent of the Company. Subject to the foregoing, the
terms of this Warrant shall be binding upon the executors, administrators, heirs, successors and assigns of the Holder. 

(b)             Each certificate representing (i) this Warrant,
(ii) the Preferred Stock, (iii) shares of the Company’s Common Stock issued upon conversion of the Preferred Stock and (iv) any other securities issued in respect to the Preferred Stock or Common Stock issued upon conversion of
the Preferred Stock upon any stock split, stock dividend, recapitalization, merger, consolidation or similar event, shall (unless otherwise permitted by the provisions of this Section 2 or unless such securities have been registered under the
Securities Act or sold under Rule 144) be stamped or otherwise imprinted with a legend substantially in the following form (in addition to any legend required under applicable state securities laws): 

THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE BEEN ACQUIRED FOR INVESTMENT AND NOT WITH A VIEW TO, OR IN CONNECTION WITH, THE SALE AND DISTRIBUTION
THEREOF, AND HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OR ANY STATE SECURITIES LAWS. SUCH SECURITIES MAY NOT BE SOLD OR TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR AN OPINION OF COUNSEL IN A FORM REASONABLY ACCEPTABLE TO THE COMPANY
THAT SUCH REGISTRATION IS NOT REQUIRED DUE TO AN EXEMPTION THEREFROM UNDER SAID ACT AND ANY APPLICABLE STATE SECURITIES LAWS. 

  
 3 









(c)            The Holder of each certificate representing
Preferred Stock issued upon conversion of the Preferred Stock agrees to comply in all respects with the provisions of this Section 2. Prior to any proposed transfer of any Preferred Stock unless there is in effect a registration statement under
the Securities Act covering the proposed transfer, the Holder thereof shall give written notice to the Company of such Holder’s intention to effect such transfer. Each such notice shall describe the manner and circumstances of the proposed
transfer in sufficient detail, and shall be accompanied (except in transactions in compliance with Rule 144) by either (i) a written opinion of legal counsel who shall be reasonably satisfactory to the Company addressed to the Company and
reasonably satisfactory in form and substance to the Company’s counsel, to the effect that the proposed transfer of the Preferred Stock may be effected without registration under the Securities Act, or (ii) a “no action” letter
from the Commission to the effect that the transfer of such securities without registration will not result in a recommendation by the staff of the Commission that action be taken with respect thereto, whereupon the Holder of such Preferred Stock
shall be entitled to transfer such Preferred Stock in accordance with the terms of the notice delivered by the Holder to the Company. 
 3.            Shares to be Fully Paid; Reservation of Shares.  The Company covenants and agrees that all shares of Preferred
Stock which may be issued upon the exercise of the rights represented by this Warrant will, upon issuance, be duly authorized, validly issued, fully paid and nonassessable and free from all preemptive rights of any stockholder and free of all taxes,
liens and charges with respect to the issue thereof. The Company further covenants and agrees that during the period within which the rights represented by this Warrant may be exercised, the Company will at all times have authorized and reserved,
for the purpose of issue or transfer upon exercise of the subscription rights evidenced by this Warrant, a sufficient number of shares of authorized but unissued Preferred Stock, or other securities and property, when and as required to provide for
the exercise of the rights represented by this Warrant. The Company will take all such action as may be necessary to assure that such shares of Preferred Stock may be issued as provided herein without violation of any applicable law or regulation,
or of any requirements of any domestic securities exchange upon which the Preferred Stock may be listed. The Company will not take any action which would result in any adjustment of the Stock Purchase Price (as defined in Section 4 hereof)
(i) if the total number of shares of Preferred Stock issuable after such action upon exercise of all outstanding warrants, together with all shares of Preferred Stock then outstanding and all shares of Preferred Stock then issuable upon
exercise of all options and upon the conversion of all convertible securities then outstanding, would exceed the total number of shares of Preferred Stock then authorized by the Company’s Certificate of Incorporation, (ii) if the total
number of shares of Common Stock issuable after such action upon the conversion of all such shares of Preferred Stock together with all shares of Common Stock then outstanding and then issuable upon exercise of all options and upon the conversion of
all convertible securities then outstanding would exceed the total number of shares of Common Stock then authorized by the Company’s Certificate of Incorporation or (iii) if the par value per share of the Preferred Stock would exceed the
Stock Purchase Price. 
 4.            Adjustment of Stock
Purchase Price and Number of Shares.  The Stock Purchase Price and the number of shares purchasable upon the exercise of this Warrant shall be subject to adjustment from time to time upon the occurrence of certain events described in
this Section 4. Upon each adjustment of the Stock Purchase Price, the Holder of this Warrant shall thereafter be entitled to purchase, at the Stock Purchase Price resulting from such adjustment, the number of shares obtained by multiplying the
Stock Purchase Price in effect immediately prior to such adjustment by the number of shares purchasable pursuant hereto immediately prior to such adjustment, and dividing the product thereof by the Stock Purchase Price resulting from such
adjustment. 
 4.1            Subdivision or Combination of
Stock.  In case the Company shall at any time subdivide its outstanding shares of Preferred Stock into a greater number of shares, the Stock Purchase Price in effect immediately prior to such subdivision shall be proportionately
reduced, and conversely, in case the outstanding shares of Preferred Stock of the Company shall be combined into a smaller number of shares, the Stock Purchase Price in effect immediately prior to such combination shall be proportionately increased.

 4.2            Dividends in Preferred Stock, Other Stock,
Property, Reclassification.  If at any time or from time to time the holders of Preferred Stock (or any shares of stock or other securities at the time receivable upon the exercise of this Warrant) shall have received or become
entitled to receive, without payment therefor, 

  
 4 








 (a)            Preferred Stock,
or any shares of stock or other securities whether or not such securities are at any time directly or indirectly convertible into or exchangeable for Preferred Stock, or any rights or options to subscribe for, purchase or otherwise acquire any of
the foregoing by way of dividend or other distribution, or 

(b)            any cash paid or payable otherwise than as a cash dividend,
or 
 (c)            Preferred Stock or other or additional stock
or other securities or property (including cash) by way of spin off, split-up, reclassification, combination of shares or similar corporate rearrangement, (other than shares of Preferred Stock issued as a stock split, adjustments in respect of which
shall be covered by the terms of Section 4.1 above), 
 Then and in each such case, the Holder hereof shall, upon the exercise of this
Warrant, be entitled to receive, in addition to the number of shares of Preferred Stock receivable thereupon, and without payment of any additional consideration therefore, the amount of stock and other securities and property (including cash in the
cases referred to in clauses (b) and (c) above) which such Holder would hold on the date of such exercise had he been the holder of record of such Preferred Stock as of the date on which holders of Preferred Stock received or became
entitled to receive such shares and/or all other additional stock and other securities and property. 

4.3            Reorganization, Reclassification, Consolidation, Merger or
Sale.  If any capital reorganization of the capital stock of the Company, or any consolidation or merger of the Company with another corporation, or the sale of all or substantially all of its assets to another corporation shall be
effected in such a way that holders of Preferred Stock shall be entitled to receive stock, securities or assets with respect to or in exchange for Preferred Stock, then, as a condition of such reorganization, reclassification, consolidation, merger
or sale, lawful and adequate provisions shall be made whereby the holder hereof shall thereafter have the right to purchase and receive (in lieu of the shares of the Preferred Stock of the Company immediately theretofore purchasable and receivable
upon the exercise of the rights represented hereby) such shares of stock, securities or assets as may be issued or payable with respect to or in exchange for a number of outstanding shares of such Preferred Stock equal to the number of shares of
such stock immediately theretofore purchasable and receivable upon the exercise of the rights represented hereby. In any such case, appropriate provision shall be made with respect to the rights and interests of the holder of this Warrant to the end
that the provisions hereof (including, without limitation, provisions for adjustments of the Stock Purchase Price and of the number of shares purchasable and receivable upon the exercise of this Warrant) shall thereafter be applicable, as nearly as
may be possible, in relation to any shares of stock, securities or assets thereafter deliverable upon the exercise hereof. The Company will not effect any such consolidation, merger or sale unless, prior to the consummation thereof, the successor
corporation (if other than the Company) resulting from such consolidation or the corporation purchasing such assets shall assume by written instrument, executed and mailed or delivered to the registered Holder hereof at the last address of such
Holder appearing on the books of the Company, the obligation to deliver to such Holder such shares of stock, securities or assets as, in accordance with the foregoing provisions, such Holder may be entitled to purchase. 

4.4            Sale or Issuance Below Purchase Price.  The
other antidilution rights applicable to the shares of series Preferred Stock purchasable hereunder are set forth in the Company’s Certificate of Incorporation, as amended through the date hereof (the “Charter”). The Company shall
promptly provide the Holder hereof with any restatement, amendment, modification or waiver of the Charter promptly after the same has been made. 
 4.5            Notice of Adjustment.  Upon any adjustment of the Stock Purchase Price, and/or any increase or decrease in the
number of shares purchasable upon the exercise of this Warrant the Company shall give written notice thereof, by first class mail, postage prepaid, addressed to the registered holder of this Warrant at the address of such holder as shown on the
books of the Company. The notice, which may be substantially in the form of Exhibit “A” attached hereto, shall be signed by the Company’s chief financial officer and shall state the Stock Purchase Price resulting from such adjustment
and the increase or decrease, if any, in the number of shares purchasable at such price upon the exercise of this Warrant, setting forth in reasonable detail the method of calculation and the facts upon which such calculation is based. 

  
 5 








 4.6            Other
Notices.  If at any time: 
 (a)            the
Company shall declare any cash dividend upon its Preferred Stock; 

(b)            the Company shall declare any dividend upon its Preferred
Stock payable in stock or make any special dividend or other distribution to the holders of its Preferred Stock; 

(c)            there shall be any capital reorganization or reclassification
of the capital stock of the Company, or consolidation or merger of the Company with, or sale of all or substantially all of its assets to, another entity; 
 (d)            there shall be a voluntary or involuntary dissolution, liquidation or winding-up of the Company; or 

(e)            the Company shall take or propose to take any other action,
notice of which is actually provided to holders of the Preferred Stock; 
 then, in any one or more of said cases, the Company shall give, by
first class mail, postage prepaid, addressed to the Holder of this Warrant at the address of such Holder as shown on the books of the Company, (i) at least 10 day’s prior written notice of the date on which the books of the Company shall
close or a record shall be taken for such dividend, distribution or subscription rights or for determining rights to vote in respect of any such reorganization, reclassification, consolidation, merger, sale, dissolution, liquidation or winding-up,
or other action and (ii) in the case of any such reorganization, reclassification, consolidation, merger, sale, dissolution, liquidation or winding-up, or other action, at least 20 day’s written notice of the date when the same shall take
place. Any notice given in accordance with the foregoing clause (i) shall also specify, in the case of any such dividend, distribution or subscription rights, the date on which the holders of Preferred Stock shall be entitled thereto. Any
notice given in accordance with the foregoing clause (ii) shall also specify the date on which the holders of Preferred Stock shall be entitled to exchange their Preferred Stock for securities or other property deliverable upon such
reorganization, reclassification, consolidation, merger, sale, dissolution, liquidation or winding-up, or other action as the case may be. 
 4.7            Certain Events.  If any change in the outstanding Preferred Stock of the Company or any other event occurs as to
which the other provisions of this Section 4 are not strictly applicable or if strictly applicable would not fairly effect the adjustments to this Warrant in accordance with the essential intent and principles of such provisions, then the Board
of Directors of the Company shall make in good faith an adjustment in the number and class of shares issuable under this Warrant, the Stock Purchase Price and/or the application of such provisions, in accordance with such essential intent and
principles, so as to protect such purchase rights as aforesaid. The adjustment shall be such as will give the Holder of this Warrant upon exercise for the same aggregate Stock Purchase Price the total number, class and kind of shares as the Holder
would have owned had this Warrant been exercised prior to the event and had the Holder continued to hold such shares until after the event requiring adjustment. 
 5.            Issue Tax.  The issuance of certificates for shares of Preferred Stock upon the exercise of this Warrant shall be
made without charge to the Holder of this Warrant for any issue tax in respect thereof; provided, however, that the Company shall not be required to pay any tax which may be payable in respect of any transfer involved in the issuance and delivery of
any certificate in a name other than that of the then Holder of this Warrant being exercised. 

6.            Closing of Books.  The Company will at no time
close its transfer books against the transfer of this Warrant or of any shares of Preferred Stock issued or issuable upon the exercise of this Warrant in any manner which interferes with the timely exercise of this Warrant. 

7.            No Voting or Dividend Rights; Limitation of
Liability.  Nothing contained in this Warrant shall be construed as conferring upon the Holder hereof the right to vote or to consent as a stockholder in respect of meetings of stockholders for the election of directors of the Company
or any other matters or any rights whatsoever as a stockholder of the Company. No dividends or interest shall be payable or accrued in respect of this Warrant or the interest represented hereby or the shares purchasable hereunder until, and only to
the extent that, this Warrant shall 

  
 6 








 
have been exercised. No provisions hereof, in the absence of affirmative action by the Holder to purchase shares of Preferred Stock, and no mere enumeration herein of the rights or privileges of
the Holder hereof, shall give rise to any liability of such Holder for the Stock Purchase Price or as a stockholder of the Company, whether such liability is asserted by the Company or by its creditors. 

8.            Registration Rights.  The Holder hereof shall
be entitled, with respect to the shares of Preferred Stock issued upon exercise hereof or the shares of Common Stock or other securities issued upon conversion of such Preferred Stock as the case may be, to all of the registration rights set forth
in the Amended and Restated Investors Rights Agreement dated as of January 19,2007 (the “Rights Agreement”), as amended to date, to the same extent and on the same terms and conditions as possessed by the investors thereunder with the
following exceptions and clarifications: (i) the Holder will have no demand registration rights; (ii) the Holder will be subject to the same provisions regarding indemnification as contained in the Rights Agreement; and (iii) the
registration rights are freely assignable by the Holder of this Warrant in connection with a permitted transfer of this Warrant or the shares issuable upon exercise hereof. The Company shall take such action as may be reasonably necessary to assure
that the granting of such registration rights to the Holder does not violate the provisions of the Rights Agreement or any of the Company’s charter documents or rights of prior grantees of registration rights. 

9.            Rights and Obligations Survive Exercise of
Warrant.  The rights and obligations of the Company, of the Holder of this Warrant and of the holder of shares of Preferred Stock issued upon exercise of this Warrant, contained in Sections 6 and 8 shall survive the exercise of this
Warrant. 
 10.          Modification and Waiver.  This
Warrant and any provision hereof may be changed, waived, discharged or terminated only by an instrument in writing signed by the party against which enforcement of the same is sought. 

11.          Notices.  Any notice, request or other document required
or permitted to be given or delivered to the Holder hereof or the Company shall be deemed to have been given (i) upon receipt if delivered personally or by courier (ii) upon confirmation of receipt if by telecopy or (iii) three
business days after deposit in the US mail, with postage prepaid and certified or registered, to each such Holder at its address as shown on the books of the Company or to the Company at the address indicated therefor in the first paragraph of this
Warrant. 
 12.          Binding Effect on Successors.  This
Warrant shall be binding upon any corporation succeeding the Company by merger, consolidation or acquisition of all or substantially all of the Company’s assets. All of the obligations of the Company relating to the Preferred Stock issuable
upon the exercise of this Warrant shall survive the exercise and termination of this Warrant. All of the covenants and agreements of the Company shall inure to the benefit of the successors and assign of the holder hereof. The Company will, at the
time of the exercise of this Warrant, in whole or in part, upon request of the Holder hereof but at the Company’s expense, acknowledge in writing its continuing obligation to the Holder hereof in respect of any rights (including, without
limitation, any right to registration of the shares of Common Stock) to which the holder hereof shall continue to be entitled after such exercise in accordance with this Warrant; provided, that the failure of the holder hereof to make any such
request shall not affect the continuing obligation of the Company to the Holder hereof in respect of such rights. 

13.          Descriptive Headings and Governing Law.  The descriptive
headings of the several sections and paragraphs of this Warrant are inserted for convenience only and do not constitute a part of this Warrant. This Warrant shall be construed and enforced in accordance with, and the rights of the parties shall be
governed by, the laws of the State of California. 
 14.          Lost
Warrants or Stock Certificates.  The Company represents and warrants to the Holder hereof that upon receipt of evidence reasonably satisfactory to the Company of the loss, theft, destruction, or mutilation of any Warrant or stock
certificate and, in the case of any such loss, theft or destruction, upon receipt of an indemnity reasonably satisfactory to the Company, or in the case of any such mutilation upon surrender and cancellation of such Warrant or stock certificate, the
Company at its expense will make and deliver a new Warrant or stock certificate, of like tenor, in lieu of the lost, stolen, destroyed or mutilated Warrant or stock certificate. 

  
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 15.          Fractional Shares. No
fractional shares shall be issued upon exercise of this Warrant. The Company shall, in lieu of issuing any fractional share, pay the holder entitled to such fraction a sum in cash equal to such fraction multiplied by the then effective Stock
Purchase Price. 
 16.          Representations of Holder. With respect
to this Warrant, Holder represents and warrants to the Company as follows: 

16.1        Experience. It is experienced in evaluating and investing in companies
engaged in businesses similar to that of the Company; it understands that investment in this Warrant involves substantial risks; it has made detailed inquiries concerning the Company, its business and services, its officers and its personnel; the
officers of the Company have made available to Holder any and all written information it has requested; the officers of the Company have answered to Holder’s satisfaction all inquiries made by it; in making this investment it has relied upon
information made available to it by the Company; and it has such knowledge and experience in financial and business matters that it is capable of evaluating the merits and risks of investment in the Company and it is able to bear the economic risk
of that investment. 
 16.2        Investment. It is acquiring this Warrant for
investment for its own account and not with a view to, or for resale in connection with, any distribution thereof. It understands that this Warrant, the shares of Preferred Stock issuable upon exercise thereof and the shares of Common Stock issuable
upon conversion of the Preferred Stock, have not been registered under the Securities Act, nor qualified under applicable state securities laws. Holder is an “accredited investor” within the meaning of Securities and Exchange Commission
(“SEC”) Rule 501 of Regulation D, as presently in effect, and will execute any investment representation statement requested by the Company. 
 16.3        Rule 144. It acknowledges that this Warrant, the Preferred Stock and the Common Stock must be held indefinitely unless they are subsequently
registered under the Securities Act or an exemption from such registration is available. It has been advised or is aware of the provisions of Rule 144 promulgated under the Securities Act. 

16.4        Access to Data. It has had an opportunity to discuss the Company’s
business, management and financial affairs with the Company’s management and has had the opportunity to inspect the Company’s facilities. 
 17.          Additional Representations and Covenants of the Company. The Company hereby represents, warrants and agrees as follows: 

17.1        Corporate Power. The Company has all requisite corporate power and corporate
authority to issue this Warrant and to carry out and perform its obligations hereunder. 

17.2        Authorization. All corporate action on the part of the Company, its directors
and stockholders necessary for the authorization, execution, delivery and performance by the Company of this has been taken. This Warrant is a valid and binding obligation of the Company, enforceable in accordance with its terms. 

17.3        Offering. Subject in part to the truth and accuracy of Holder’s
representations set forth in Section 16 hereof, the offer, issuance and sale of this Warrant is, and the issuance of Preferred Stock upon exercise of this Warrant and the issuance of Common Stock upon conversion of the Preferred Stock will be
exempt from the registration requirements of the Securities Act, and are exempt from the qualification requirements of any applicable state securities laws; and neither the Company nor anyone acting on its behalf will take any action hereafter that
would cause the loss of such exemptions. 
 17.4        Stock Issuance. Upon
exercise of this Warrant, the Company will use its best efforts to cause stock certificates representing the shares of Preferred Stock purchased pursuant to the exercise to be issued in the names of Holder, its nominees or assignees, as appropriate
at the time of such exercise. Upon conversion of the shares of Preferred Stock into shares of Common Stock, the Company will issue the Common Stock in the names of Holder, its nominees or assignees, as appropriate. 

  
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 17.5        Certificates and By-Laws. The
Company has provided Holder with true and complete copies of the Company’s Certificate of Incorporation, By-Laws, and each Certificate of Designation or other charter document setting, forth any rights, preferences and privileges of
Company’s capital stock, each as amended and in effect on the date of issuance of this Warrant. 

17.6        Conversion of Preferred Stock. As of the date hereof, each share of the
Preferred Stock is convertible into one share of the Common Stock. 

17.7        Financial and Other Reports. From time to time up to the earlier of the
Expiration Date or the complete exercise of this Warrant, the Company shall furnish to Holder (i) within 90 days after the close of each fiscal year of the Company an audited balance sheet and statement of changes in financial position at and
as of the end of such fiscal year, together with an audited statement of income for such fiscal year; (ii) within 45 days after the close of each fiscal quarter of the Company, an unaudited balance sheet and statement of cash flows at and as of
the end of such quarter, together with an unaudited statement of income for such quarter; and (iii) promptly after sending, making available, or filing, copies of all reports, proxy statements, and financial statements that the Company sends or
makes available to its stockholders and all registration statements and reports that the Company files with the SEC or any other governmental or regulatory authority. 
 IN WITNESS WHEREOF, Company has caused this Warrant to be duly executed by its officer, thereunto duly authorized as of the date of issuance set forth on the first page hereof. 

ENVIVIO, INC 
  

			
	 By:
	 	 /s/ Albert Liong

		
	 Title:
	 	 CFO



  
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 FORM OF SUBSCRIPTION 
 (To be signed only upon exercise of Warrant) 
 To:      ENVIVIO,
INC. 
  

	 ̈	The undersigned, the holder of the within Warrant, hereby irrevocably elects to exercise the purchase right represented by such Warrant for, and to purchase thereunder,
(1) See Below                     
(                )shares (the “Shares”) of Stock of
                     and herewith makes payment of
                     Dollars ($            ) therefor, and requests
that the certificates for such shares be issued in the name of, and delivered to,                     , whose address is
                    . 

  

	 ̈	The undersigned hereby elects to convert      percent (    %) of the value of the Warrant pursuant to the
provisions of Section 1(b) of the Warrant. 

 The undersigned acknowledges that it has reviewed the representations and
warranties contained in Section 17 of this Warrant and by its signature below hereby makes such representations and warranties to the Company. 
  

							
		 	Dated	  	  
	  	
				
		 	Holder:	  	  
	  	
				
		 	By:	  	  
	  	
				
		 	Its:	  	  
	  	
			
		 	(Address)	  	
			
		 	                           
                                         
        	  	
			
		 	                           
                                         
        	  	

  

	(1)	Insert here the number of shares called for on the face of the Warrant (or, in the case of a partial exercise, the portion thereof as to which the Warrant is being
exercised), in either case without making any adjustment for additional Preferred Stock or any other stock or other securities or property or cash which, pursuant to the adjustment provisions of the Warrant, may be issuable upon exercise.









 ASSIGNMENT 
 FOR VALUE RECEIVED, the undersigned, the holder of the within Warrant, hereby sells, assigns and transfers all of the rights of the undersigned under the within Warrant, with respect to the number of
shares of Preferred Stock covered thereby set forth herein below, unto: 
  

					
	Name of Assignee	  	Address	  	No. of Shares
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	
		  		  	

  

					
		 	Dated	  	  

			
		 	Holder:	  	  

			
		 	By:	  	  

			
		 	Its:	  	  









 EXHIBIT “A” 

[On letterhead of the Company] 
 Reference is hereby made to that certain Warrant dated May __, 2008 issued by ENVIVIO, INC, a Delaware corporation (the “Company”), to VENTURE LENDING & LEASING V, INC., a Maryland
corporation (the “Holder”). 
 [IF APPLICABLE] The Warrant provides that the actual number of shares of the
Company’s capital stock issuable upon exercise of the Warrant and the initial exercise price per share are to be determined by reference to one or more events or conditions subsequent to the issuance of the Warrant. Such events or conditions
have now occurred or lapsed, and the Company wishes to confirm the actual number of shares issuable and the initial exercise price. The provisions of this Supplement to Warrant are incorporated into the Warrant by this reference, and shall control
the interpretation and exercise of the Warrant. 
 [IF APPLICABLE] Notice is hereby given pursuant to Section 4.5 of the
Warrant that the following adjustment(s) have been made to the Warrant: [describe adjustments, setting forth details regarding method of calculation and facts upon which calculation is based]. 

This certifies that the Holder is entitled to purchase from the Company
                    
(                    ) fully paid and nonassessable shares of the Company’s
                     Stock at a price of
                     Dollars ($            ) per share (the
“Stock Purchase Price”). The Stock Purchase Price and the number of shares purchasable under the Warrant remain subject to adjustment as provided in Section 4 of the Warrant. 

Executed this      day of             ,
200    . 
  

					
	ENVIVIO, INC	 	
			
	By:	 	  
	 	
			
	Name:	 	  
	 	
			
	Title: