Warrant to Purchase Series A Preferred Stock between Plumtree Software, Inc. and Lighthouse Capital Partners II, L.P.

Summary

This agreement is a warrant issued by Plumtree Software, Inc. to Lighthouse Capital Partners II, L.P., allowing the holder to purchase a specified number of shares of Series A Preferred Stock or, under certain conditions, shares from a future preferred stock round. The warrant sets the purchase price, outlines payment methods, and provides for adjustments and partial exercises. It expires on March 31, 2004, and includes provisions for automatic exercise and share reservation by the company.

EX-4.3 2 0002.txt WARRANT TO PURCHASE SERIES A PREFERRED STOCK EXHIBIT 4.3 THIS WARRANT HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE "1933 ACT"), OR ANY APPLICABLE STATE SECURITIES LAWS, AND MAY NOT BE SOLD OR TRANSFERRED UNLESS SUCH SALE OR TRANSFER IS IN ACCORDANCE WITH THE REGISTRATION REQUIREMENTS OF SUCH ACT AND APPLICABLE LAWS OR SOME OTHER EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT AND APPLICABLE LAWS IS AVAILABLE WITH RESPECT THERETO. PREFERRED STOCK PURCHASE WARRANT Warrant No. _________ PLUMTREE SOFTWARE INC Void after March 31, 2004 1. Issuance. This Warrant is issued to LIGHTHOUSE CAPITAL PARTNERS II, L.P. by PLUMTREE SOFTWARE, INC., a California corporation (hereinafter with its successors called the "Company"). 2. Purchase Price; Number of Shares. The registered holder of this Warrant (the "Holder"), commencing on the date hereof, is entitled upon surrender of this Warrant with the subscription form annexed hereto duly executed, at the principal office of the Company, to purchase from the Company the following securities (collectively, the "Shares") at a price per share (the "Next Round Purchase Price") equal to the price per share of the Company's next round of preferred stock raising at least $2,500,000 upon substantially the terms set forth in Exhibit C (the "Next Round"), that number of fully paid and nonassessable shares of preferred stock offered in the Next Round (the "Next Round Preferred Stock") equal to $14,000 divided by the Next Round Purchase Price; provided however, that if (a) the Next Round does not close on or before May 31, 1997, or (b) there is a Reorganization (defined below) on or before May 31, 1997, then Holder shall be entitled to purchase, at a price per share equal to $0.58 (the "Series A Purchase Price"), 24,137 fully paid and nonassessable shares of Series A Preferred Stock, no par value, of the Company (the "Series A Preferred Stock"). (The Next Round Purchase Price and the Series A Purchase Price are sometimes referred to herein collectively, as the "Purchase Price" and the Next Round Preferred Stock and the Series A Preferred Stock are sometimes referred to herein collectively, as the "Preferred Stock"). Until such time as this Warrant is exercised in full or expires, the Purchase Price and the securities issuable upon exercise of this Warrant are subject to adjustment as hereinafter provided. The person or persons on whose name or names any certificate representing shares of Preferred Stock is issued hereunder shall be deemed to have become the holder of record of the shares represented thereby as at the close of business on the date this Warrant is exercised with respect to such shares, whether or not the transfer books of the Company shall be closed. 3. Payment of Purchase Price. The Purchase Price may be paid (i) in cash or by check, (ii) by the surrender by the Holder to the Company of any promissory notes or other obligations issued by the Company, with all such notes and obligations so surrendered being credited against the Purchase Price in an amount equal to the principal amount thereof plus accrued interest to the date of surrender, or (iii) by any combination of the foregoing. 4. Net Issue Election. The Holder may elect to receive, without the payment by the Holder of any additional consideration, shares of Preferred Stock equal to the value of this Warrant or any portion hereof by the surrender of this Warrant or such portion to the Company, with the net issue election notice annexed hereto duly executed, at the principal office of the Company. Thereupon, the Company shall issue to the Holder such number of fully paid and nonassessable shares of Preferred Stock as is computed using the following formula: X = Y(A-B) ------ A where: X = the number of shares of Preferred Stock to be issued to the Holder pursuant to this Section 4. Y = the number of shares of Preferred Stock covered by this Warrant in respect of which the net issue election is made pursuant to this Section 4. A = the Fair Market Value (defined below) of one share of Preferred Stock, as determined at the time the net issue election is made pursuant to this Section 4. B = the Purchase Price in effect under this Warrant at the time the net issue election is made pursuant to this Section 4. "Fair Market Value" of a share of Preferred Stock (or Common Stock if the Preferred Stock has been automatically converted into Common Stock) as of a particular date (the "Determination Date") shall mean: (i) If the net issue election is made in connection with and contingent upon the closing of the sale of the Company's Common Stock to the public in a public offering pursuant to a Registration Statement under the Act (a "Public Offering"), and if the Company's Registration Statement relating to such Public Offering ("Registration Statement") has been declared effective by the SEC, then the initial "Price to Public" specified in the final prospectus with respect to such offering multiplied by the number of shares of Common Stock into which each share of Preferred Stock is then convertible. (ii) If the net issue election is not made in connection with and contingent upon a Public Offering, then as follows: (A) If traded on a securities exchange or the Nasdaq National Market, the fair market value of the Common Stock shall be deemed to be the average of the closing or last reported sale prices of the Common Stock on such exchange or market over the 30-day period ending five business days prior to the Determination Date, and the fair market value of the Preferred Stock shall be deemed to be such fair market value of the Common Stock multiplied by the number of shares of Common Stock into which each share of Preferred Stock is then convertible; (B) If otherwise traded in an over-the-counter market, the fair market value of the Common Stock shall be deemed to be the average of the closing ask prices of the Common Stock over the 30-day period ending five business days prior to the Determination Date, and the fair market value of the Preferred Stock shall be deemed to be such fair market value of the Common Stock multiplied by the number of shares of Common Stock into which each share of Preferred Stock is then convertible; and (C) If there is no public market for the Common Stock, then fair market value shall be determined in good faith by the Company's Board of Directors. 5. Partial Exercise. This Warrant may be exercised in part, and the Holder shall be entitled to receive a new warrant, which shall be dated as of the date of this Warrant, covering the number of shares in respect of which this Warrant shall not have been exercised. 6. Fractional Shares. In no event shall any fractional share of Preferred Stock be issued upon any exercise of this Warrant. If, upon exercise of this Warrant as an entirety, the Holder would, except as provided in this Section 6, be entitled to receive a fractional share of Preferred Stock, then the Company shall make a cash payment therefore based upon the Purchase Price then in effect. 7. Expiration Date; Automatic Exercise. This Warrant shall expire at the close of business on March 31, 2004, and shall be void thereafter. Notwithstanding the foregoing, this Warrant shall automatically be deemed to be exercised in full pursuant to the provisions of Section 4 hereof, without any further action on behalf of the Holder, immediately prior to the time this Warrant would otherwise expire pursuant to the preceding sentence. 8. Reserved Shares; Valid Issuance. The Company covenants that it will at all times from and after June 5, 1997 reserve and keep available such number of its authorized shares of Preferred Stock and Common Stock, no par value, of the Company (the "Common Stock"), free from all preemptive or similar rights therein, as will be sufficient to permit, respectively, the exercise of this Warrant in full and the conversion into shares of Common Stock of all shares of Preferred Stock receivable upon such exercise. The Company further covenants that such shares as may be issued pursuant to such exercise and/or conversion will, upon issuance, be duly and validly issued, fully paid and nonassessable and free from all taxes, liens and charges with respect to the issuance thereof. 9. Stock Splits and Dividends. If after the date hereof the Company shall subdivide the Preferred Stock, by split-up or otherwise, or combine the Preferred Stock, or issue additional shares of Preferred Stock in payment of a stock dividend on the Preferred Stock, the number of shares of Preferred Stock issuable on the exercise of this Warrant shall forthwith be proportionately increased in the case of a subdivision or stock dividend, or proportionately decreased in the case of a combination, and the Purchase Price shall forthwith be proportionately decreased in the case of a subdivision or stock dividend, or proportionately increased in the case of a combination. 10. Adjustments for Diluting Issuances. The other antidilution rights applicable to the Preferred Stock and the Common Stock of the Company are set forth in the Amended and Restated Articles of Incorporation, as amended from time to time (the "Articles"), a true and complete copy in its current form which is attached hereto as Exhibit A. Such rights shall not be restated, amended or modified in any manner which effects the Holder differently than the holders of Series A Preferred without such Holder's prior written consent. The Company shall promptly provide the Holder hereof with any restatement, amendment or modification to the Articles promptly after the same has been made. 11. Mergers and Reclassifications. If after the date hereof the Company shall enter into any Reorganization (as hereinafter defined), then the Holder shall thereafter have the right to purchase, at a total price not to exceed that payable upon the exercise of this Warrant in full, the kind and amount of shares of stock and other securities and property receivable upon such Reorganization by a holder of the number of shares of Preferred Stock which might have been purchased by the Holder immediately prior to such Reorganization, and in any such case appropriate provisions shall be made with respect to the rights and interest of the Holder to the end that the provisions hereof (including without limitation, provisions for the adjustment of the Purchase Price and the number of shares issuable hereunder and the provisions relating to the net issue election) shall thereafter be applicable in relation to any shares of stock or other securities and property thereafter deliverable upon exercise hereof. For the purposes of this Section 11, the term "Reorganization" shall include without limitation any reclassification, capital reorganization or change of the Preferred Stock (other than as a result of a subdivision, combination or stock dividend provided for in Section 9 hereof or a change in par value or from par value to no par value or no par value to par value), or any consolidation of the Company with, or merger of the Company into, another corporation or other business organization (other than a merger in which the Company is the surviving corporation and which does not result in any reclassification or change of the outstanding Preferred Stock), or any sale or conveyance to another corporation or other business organization of all or substantially all of the assets of the Company. 12. Certificate of Adjustment. Whenever the Purchase Price is adjusted, as herein provided, the Company shall promptly deliver to the Holder a certificate of the Company's chief financial officer setting forth the Purchase Price after such adjustment and setting forth a brief statement of the facts requiring such adjustment. 13. Notices of Record Date, Etc. In the event of: (a) any taking by the Company of a record of the holders of any class of securities for the purpose of determining the holders thereof who are entitled to receive any dividend or other distribution, or any right to subscribe for, purchase, sell or otherwise acquire or dispose of any shares of stock of any class or any other securities or property, or to receive any other right; (b) any reclassification of the capital stock of the Company, capital reorganization of the Company, consolidation or merger involving the Company, or sale or conveyance of all or substantially all of its assets; or (c) any voluntary or involuntary dissolution, liquidation or winding- up of the Company; then in each such event the Company will provide or cause to be provided to the Holder the notice as provided to the holders of the Preferred Stock or Common Stock, whichever is applicable, as set forth in the Company's Articles, by-laws, or the California Corporations Code. 14. Representations, Warranties and Covenants. This Warrant is issued and delivered by the Company and accepted by each Holder on the basis of the following representations, warranties and covenants made by the Company: A. The Company has all necessary authority to issue, execute and deliver this Warrant and to perform its obligations hereunder. This Warrant has been duly authorized issued, executed and delivered by the Company and is the valid and binding obligation of the Company, enforceable in accordance with its terms. B. The shares of Series B Preferred Stock issuable upon the exercise of this Warrant have been duly authorized and reserved for issuance by the Company and, when issued in accordance with the terms hereof, will be validly issued, fully paid and nonassessable. C. The issuance, execution and delivery of this Warrant do not, and the issuance of the shares of Preferred Stock upon the exercise of this Warrant in accordance with the terms hereof will not, (i) violate or contravene the Company's Articles or by-laws, or any law, statute, regulation, rule, judgment or order applicable to the Company, (ii) violate, contravene or result in a breach or default under any material contract, agreement or instrument to which the Company is a party or by which the Company or any of its assets are bound or (iii) require the consent or approval of or the filing of any notice or registration with any person or entity except for the filing of notice pursuant to federal and state securities laws which, if required, the Company covenants and agrees to file within the prescribed period. D. So long as this Warrant has not terminated, Holder shall be entitled to receive such financial and other information as the Holder would be entitled to receive under the Series A and Series B Preferred Stock Purchase Agreement if Holder were a holder of that number of shares issuable upon full exercise of this Warrant. E. As of the date hereof, the authorized capital stock of the Company consists of (i) 15,971,421 shares of Common Stock, of which 3,200,000 shares are issued and outstanding and 2,800,000 shares of which are reserved for future issuance to key employees pursuant to the Company's equity incentive plan and as founder's stock to key employees and 14,141 shares are reserved for issuance upon the exercise of this Warrant and the conversion of the Preferred Stock issued upon such exercise, (ii) 948,276 shares of Series A Preferred Stock, all of which are issued and outstanding shares, and (iii) 3,080,303 shares of Series B Preferred Stock, none of which are issued and outstanding shares and 3,050,303 shares of which are reserved for future issuance pursuant to the Series A and Series B Stock Purchase Agreement and 14,141 shares are reserved for issuance upon the exercise of this Warrant. Attached hereto as Exhibit B is a capitalization table summarizing the capitalization of the Company, including, without limitation, the current Conversion Price of the Series A Preferred Stock and Series B Preferred Stock. 15. Registration Rights. The Company grants to the Holder registration rights contained in Section 2 of the Company's Investor Rights Agreement dated as of February 13, 1997 (the "Investor Rights Agreement"), so that (i) the shares of Common Stock issuable upon conversion of the shares of Preferred Stock issuable upon exercise of this Warrant shall be "Registrable Securities". 16. Amendment. The terms of this Warrant may be amended, modified or waived only with the written consent of the Holder. 17. Representations and Covenants of the Holder. This Preferred Stock Purchase Warrant has been entered into by the Company in reliance upon the following representations and covenants of the Holder, which by its execution hereof the Holder hereby confirms: A. Investment Purpose. The right to acquire Preferred Stock or the Preferred Stock issuable upon exercise of the Holder's rights contained herein will be acquired for investment and not with a view to the sale or distribution of any part thereof, and the Holder has no present intention of selling or engaging in any public distribution of the same except pursuant to a registration or exemption. B. Accredited Investor. Holder is an "accredited investor" within the meaning of the Securities and Exchange Rule 501 of Regulation D, as presently in effect. C. Private Issue. The Holder understands (i) that the Preferred Stock issuable upon exercise of the Holder's rights contained herein is not registered under the 1933 Act or qualified under applicable state securities laws on the ground that the issuance contemplated by this Warrant will be exempt from the registration and qualifications requirements thereof, and (ii) that the Company's reliance on such exemption is predicated on the representations set forth in this Section 17. D. Financial Risk. The Holder has such knowledge and experience in financial and business matters as to be capable of evaluating the merits and risks of its investment and has the ability to bear the economic risks of its investment. 18. Notices, Transfers, Etc. A. Any notice or written communication required or permitted to be given to the Holder may be given by certified mail or delivered to the Holder at the address most recently provided by the Holder to the Company. B. Subject to compliance with applicable federal and state securities laws, this Warrant may be transferred by the Holder with respect to any or all of the shares purchasable hereunder. Upon surrender of this Warrant to the Company, together with the assignment notice annexed hereto duly executed, for transfer of this Warrant as an entirety by the Holder, the Company shall issue a new warrant of the same denomination to the assignee. Upon surrender of this Warrant to the Company, together with the assignment hereof properly endorsed, by the Holder for transfer with respect to a portion of the shares of Preferred Stock purchasable hereunder, the Company shall issue a new warrant to the assignee, in such denomination as shall be requested by the Holder hereof, and shall issue to such Holder a new warrant covering the number of shares in respect of which this Warrant shall not have been transferred. C. In case this Warrant shall be mutilated, lost, stolen or destroyed, the Company shall issue a new warrant of like tenor and denomination and deliver the same (i) in exchange and substitution for and upon surrender and cancellation of any mutilated Warrant, or (ii) in lieu of any Warrant lost, stolen or destroyed, upon receipt of an affidavit of the Holder or other evidence reasonably satisfactory to the Company of the loss, theft or destruction of such Warrant. 19. No Impairment. The Company will not, by amendment of its Articles or through any reclassification, capital reorganization, consolidation, merger, sale or conveyance of assets, dissolution, liquidation, issue or sale of securities or any other voluntary action, avoid or seek to avoid the observance of performance of any of the terms of this Warrant, but will at all times in good faith assist in the carrying out of all such terms and in the taking of all such action as may be necessary or appropriate in order to protect the rights of the Holder. 20. Governing Law. The provisions and terms of this Warrant shall be governed by and construed in accordance with the internal laws of the State of California. 21. Successors and Assigns. This Warrant shall be binding upon the Company's successors and assigns and shall inure to the benefit of the Holder's successors, legal representatives and permitted assigns. 22. Business Days. If the last or appointed day for the taking of any action required or the expiration of any rights granted herein shall be a Saturday or Sunday or a legal holiday in California, then such action may be taken or right may be exercised on the next succeeding day which is not a Saturday or Sunday or such a legal holiday. 23. Qualifying Public Offering. If the Company shall effect a firm commitment underwritten public offering of shares of Common Stock which results in the conversion of the Preferred Stock into Common Stock pursuant to the Company's Articles in effect immediately prior to such offering, then, effective upon such conversion, this Warrant shall change from the right to purchase shares of Preferred Stock to the right to purchase shares of Common Stock, and the Holder shall thereupon have the right to purchased, at a total price equal to that payable upon the exercise of this Warrant in full, the number of shares of Common Stock which would have been receivable by the Holder upon the exercise of this Warrant for shares of Preferred Stock immediately prior to such conversion of such shares of Preferred Stock into shares of Common Stock, and in such event appropriate provisions shall be made with respect to the rights and interest of the Holder to the end that the provisions hereof (including, without limitation, the provisions for the adjustment of the Purchase Price and of the number of shares purchasable upon exercise of this Warrant and the provisions relating to the net issue election) shall thereafter be applicable to any shares of Common Stock deliverable upon the exercise hereof. 24. Value. The Company and the Holder agree that the value of this Warrant on the date of grant is $100. Dated: April 8, 1997 PLUMTREE SOFTWARE, INC. ----------------------- By: /s/ KIRILL SHEYNKMAN --------------------------------- [CORPORATE SEAL] Name: Kirill Sheynkman ------------------------------- Title: President and CEO ------------------------------ Attest: _____________________________ Subscription To: ____________________________ Date: ___________________________ The undersigned hereby subscribes for _______________________________ shares of Preferred Stock covered by this Warrant. The certificate(s) for such shares shall be issued in the name of the undersigned or as otherwise indicated below: ____________________________________ Signature ____________________________________ Name for Registration ____________________________________ Mailing Address Net Issue Election Notice To: _________________________ Date:__________________________ The undersigned hereby elects under Section 4 to surrender the right to purchase ____________________ shares of Preferred Stock pursuant to this Warrant. The certificate(s) for such shares issuable upon such net issue election shall he issued in the name of the undersigned or as otherwise indicated below: ____________________________________ Signature ____________________________________ Name for Registration ____________________________________ Mailing Address Assignment For value received _____________________________________________ hereby sells, assigns and transfers unto ______________________________________________ ________________________________________________________________________________ [Please print or typewrite name and address of Assignee] ________________________________________________________________________________ the within Warrant, and does hereby irrevocably constitute and appoint _________________________________ its attorney to transfer the within Warrant on the books of the within named Company with full power of substitution on the premises. Dated: ___________________________ In the Presence of __________________________________