EXHIBIT 4.6
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. _____ Number of Shares 9,375
Series D Preferred Sock
Plumtree Software, Inc,
Void after August 31, 2006
1. Issuance. This Warrant is issued to Lighthouse Capital Partners III,
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"):
(a) at a price per share of $1.60 (the "Purchase Price"), 9,375 fully
paid and nonassessable shares of Series D Preferred Stock, of the Company (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 in 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 1933 Act (a "Public Offering"),
and if the Company's Registration Statement relating to such
Public Offering ("Registration Statement") has been declared
effective by the Securities and Exchange Commission, 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 five 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 Stuck 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 five 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 in its 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 August 31, 2006, and shall be void thereafter (the
"Expiration Date"). 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 the date hereof reserve and keep available such number
of its authorized shares of Preferred Stock and Common Stock
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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 affects the Holder differently than the
holders of Series D 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, as a
condition of such Reorganization, lawful provisions shall be made, and duly
executed documents evidencing the same from the Company or its successor shall
be delivered to the Holder, so that 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 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:
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then in each such event the Company will provide or cause to be provided to the
Holder a written notice thereof. Such notice shall be provided at least twenty
(20) business days prior to the date specified in such notice on which any such
action is to be taken.
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 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 or 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 D 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 will consist of (a) 23,400,000 shares of Common Stock, 4,252,898 shares
of which are issued and outstanding, and 5,414,063 shares of which are reserved
for future issuance upon the exercise of options granted pursuant to the
Company's 1997 Equity Incentive Plan, and (b) 13,656,633 shares of Preferred
Stock (i) 1,458,621 of which are designated Series A, of which 1,422,414 are
issued and outstanding and 36,207 are reserved for future issuance to Lighthouse
Capital Partners II, L.P. pursuant to warrants issued in connection with an
equipment lease financing of the Company, (ii) 3,030,303 of which are designated
Series B, all of which are issued and outstanding, (iii) 4,699,155 of which are
Series C, 4,677,520 of which are issued and outstanding and 21,635 of which are
reserved for future issuance to Silicon Valley Bank pursuant to warrants issued
in connection with a bridge loan to the Company, and (iv) 4,468,554 of which are
designated Series D, of which 3,773,585 are issued and outstanding and 66,038 of
which are reserved for future issuance to Silicon Valley Bank pursuant to
warrants issued in connection with a bridge loan to the Company, and 9,375 of
which are reserved for future issuance pursuant to this Warrant. Attached hereto
as Exhibit B is a capitalization table summarizing the capitalization of the
Company.
15. Registration Rights. The Company grants to the Holder registration
rights contained in Section 2 of the Company's Amended and Restated Investor
Rights Agreement dated as of August 4, 1999 (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," and "Shares," and (ii) the Holder shall be a "Holder" and an
"Investor" for all purposes of such Investor Rights Agreement.
16. Right of Participation. The Company grants to the Holder the right of
participation set forth in Section 4 of the Investor Rights Agreement.
17. Amendment. The terms or this Warrant may be amended, modified or
waived only with the written consent of the Holder.
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18. 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 18.
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.
19. 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 purchaseable 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.
20. 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.
21. 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.
22. 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.
5
23. 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.
24. 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 purchase, 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.
25. Value. The Company and the Holder agree that the value of this Warrant
on the date of grant is $100.
Dated: September 1, 1999 PLUMTREE SOFTWARE, INC.
By: /s/ XXXX XXXXX
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Name: Xxxx Xxxxx
-------------------------
Title: President and CEO
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