Document:

<PAGE>

                                                                     EXHIBIT 4.4

THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER
THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE SOLD, PLEDGED, OR
OTHERWISE TRANSFERRED WITHOUT AN EFFECTIVE REGISTRATION THEREOF UNDER SUCH ACT
OR PURSUANT TO RULE 144 OR AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE
CORPORATION AND ITS COUNSEL, THAT SUCH REGISTRATION IS NOT REQUIRED.

                           WARRANT TO PURCHASE STOCK

Corporation: PLUMTREE SOFTWARE, INC., a California corporation ("Company")

Number of Shares: 18,750

Class of Stock: (i) the Company's Series C Preferred Stock to be authorized and
sold in its next venture financing if such venture financing closes within 90
days after the Issue Date (the "Next Venture Financing") or (ii) if such venture
financing does not close within 90 days after the Issue Date, additional shares
of the Company's Series B Preferred Stock to be authorized in such event (the
"Shares" in either case, as applicable)

Initial Exercise Price: (i) the per share sale price of the Series C Preferred
Stock in the Next Venture Financing, if the Shares are Series C Preferred Stock
or (ii) $0.99 per share, if the Shares are Series B Preferred Stock

Issue Date: April 20, 1998

Expiration Date: the earlier of (i) the fifth anniversary of the Issue Date and
(ii) the closing of the initial registered public offering of the Company's
common stock

     THIS WARRANT CERTIFIES THAT, for the agreed upon value of $1.00 and for
other good and valuable consideration, SILICON VALLEY BANK ("Holder") is
entitled to purchase the number of fully paid and nonassessable Shares of the
Company at the Initial Exercise Price per Share as set forth above and as
adjusted pursuant to Article 2 of this Warrant (the "Warrant Price"), subject to
the provisions and upon the terms and conditions set forth in this Warrant.
<PAGE>

ARTICLE 1. EXERCISE.
           --------

  1.1 Method of Exercise. Holder may exercise this Warrant by delivering a duly
      ------------------
executed Notice of Exercise in substantially the form attached as Appendix 1 to
the principal office of the Company. Unless Holder is exercising the conversion
right set forth in Section 1.2, Holder shall also deliver to the Company a check
for the aggregate Warrant Price for the Shares being purchased.

  1.2 Conversion Right. In lieu of exercising this Warrant as specified in
      ----------------
Section 1.1, Holder may convert this Warrant, in whole but not in part, into a
number of Shares determined by dividing (a) the aggregate fair market value of
the Shares or other securities otherwise issuable upon exercise of this Warrant
minus the aggregate Warrant Price of such Shares by (b) the fair market value of
one Share. The fair market value of the Shares shall be determined pursuant to
Section 1.4.

  1.3 [Intentionally Omitted]

  1.4 Fair Market Value. If the Shares are traded in a public market, the fair
      -----------------
market value of the Shares shall be the average of the closing prices of the
Shares (or the closing price of the Company's stock into which the Shares are
convertible) reported for the five business days immediately before Holder
delivers its Notice of Exercise to the Company, or if there have been no sales
on any such business day, the average of the highest bid and lowest asked price
at the end of such business day. If the Shares are not traded in a public
market, the Board of Directors of the Company shall determine fair market value.
The foregoing notwithstanding, if Holder advises the Board of Directors in
writing that Holder disagrees with such determination, then the Company and
Holder shall promptly agree upon a reputable investment banking firm to
undertake such valuation. If the valuation of such investment banking firm is
greater than that determined by the Board of Directors, then all fees and
expenses of such investment banking firm shall be paid by the Company. In all
other circumstances, such fees and expenses shall be paid by Holder.

  1.5 [Intentionally Omitted]

  1.6 Replacement of Warrants. On receipt of evidence reasonably satisfactory to
      -----------------------
the Company of the loss, theft, destruction or mutilation of this Warrant and,
in the case of loss, theft or destruction, on delivery of an indemnity agreement
reasonably satisfactory in form and amount to the Company or, in the case of
mutilation, on surrender and cancellation of this Warrant, the Company at its
expense shall execute and deliver, in lieu of this Warrant, a new warrant of
like tenor.

                                      -2-
<PAGE>

  1.7  Repurchase on Sale, Merger, or Consolidation of the Company.
       -----------------------------------------------------------

      1.7.1.  "Acquisition". For the purpose of this Warrant, "Acquisition"
               -----------
means any sale, license, or other disposition of all or substantially all of the
assets of the Company, or any reorganization, consolidation, or merger of the
Company where the holders of the Company's securities before the transaction
beneficially own less than 50% of the outstanding voting securities of the
surviving entity after the transaction.

      1.7.2.  Assumption of Warrant. Upon the closing of any Acquisition the
              ---------------------
successor entity shall assume the obligations of this Warrant, and this Warrant
shall be exercisable for the same securities, cash, and property as would be
payable for the Shares issuable upon exercise of the unexercised portion of this
Warrant as if such Shares were outstanding on the record date for the
Acquisition and subsequent closing, and the Warrant Price shall be adjusted
accordingly; provided that if pursuant to such Acquisition the entire
             --------
outstanding class of the Shares issuable upon exercise of the unexercised
portion of this Warrant are cancelled and the total consideration payable to the
holders of such class of Shares consists entirely of cash, then, upon payment to
the holder of this Warrant of an amount equal to the amount such holder would
receive if such holder held the Shares issuable upon exercise of the unexercised
portion of this Warrant and such Shares were outstanding on the record date for
the Acquisition less the aggregate Warrant Price of such Shares, this Warrant
                ----
shall be cancelled.

ARTICLE 2.  ADJUSTMENTS TO THE SHARES.
            -------------------------

  2.1 Stock Dividends, Splits, Etc. If the Company declares or pays a dividend
      ----------------------------
on its common stock (or the Shares if the Shares are securities other than
common stock) payable in common stock, or other securities, subdivides the
outstanding common stock into a greater amount of common stock, or, if the
Shares are securities other than common stock, subdivides the Shares in a
transaction that increases the amount of common stock into which the Shares are
convertible, then upon exercise of this Warrant, for each Share acquired, Holder
shall receive, without cost to Holder, the total number and kind of securities
to which Holder would have been entitled had Holder owned the Shares of record
as of the date the dividend or subdivision occurred.

  2.2 Reclassification, Exchange or Substitution. Except in the case of an
      ------------------------------------------
Acquisition to which the provisions of Section 1.7 are applicable, upon any
reclassification, exchange, substitution, or other event that results in a
change of the number and/or class of the securities issuable upon exercise or
conversion of this Warrant, Holder shall be entitled to receive, upon exercise
or conversion of this Warrant, the number and kind of securities and property
that Holder would have received for the Shares if this Warrant had been
exercised immediately before such reclassification, exchange, substitution, or
other event. The Company or its successor shall promptly issue to Holder a new
Warrant for such new securities or other property. The new Warrant shall provide
for adjustments which shall be as

                                      -3-
<PAGE>

nearly equivalent as may be practicable to the adjustments provided for in this
Article 2 including, without limitation, adjustments to the Warrant Price and to
the number of securities or property issuable upon exercise of the new Warrant.
The provisions of this Section 2.2 shall similarly apply to successive
reclassifications, exchanges, substitutions, or other events.

  2.3  Adjustments for Combinations, Etc. If the outstanding Shares are combined
       ---------------------------------
or consolidated, by reclassification or otherwise, into a lesser number of
shares, the Warrant Price shall be proportionately increased and the number of
Shares as to which this warrant is exercisable shall be proportionately
decreased.

  2.4  Adjustments for Diluting Issuances. The Shares shall have the some
       ----------------------------------
dilution and other protections afforded to the outstanding securities of the
same class under the provisions of the Company's Amended and Restated Articles
of Incorporation (the "Provisions"), and for the purpose of the protections
provided under the Provisions, the Shares shall be deemed to be issued and
outstanding on and after the Issue Date.

  2.5  No Impairment. The Company shall not, by amendment of its Articles of
       -------------
Incorporation or through a reorganization, transfer of assets, consolidation,
merger, dissolution, issue, or sale of securities or any other voluntary action,
avoid or seek to avoid the observance or performance of any of the terms to be
observed or performed under this Warrant by the Company, but shall at all times
in good faith assist in carrying out of all the provisions of this Article 2 and
in taking all such action as may be necessary or appropriate to protect Holder's
rights under this Article 2 against impairment.

  2.6  Fractional Shares. No fractional Shares shall be issuable upon exercise
       -----------------
or conversion of the Warrant and the number of Shares to be issued shall be
rounded down to the nearest whole Share. If a fractional share interest arises
upon any exercise or conversion of the Warrant, the Company shall eliminate such
fractional share interest by paying Holder an amount computed by multiplying the
fractional interest by the fair market value of a full Share.

  2.7  Certificate as to Adjustments. Upon each adjustment of the Warrant Price,
       -----------------------------
the Company at its expense shall promptly compute such adjustment, and furnish
Holder with a certificate of its Chief Financial Officer setting forth such
adjustment and the facts upon which such adjustment is based. The Company shall,
upon written request, furnish Holder a certificate setting forth the Warrant
Price in effect upon the date thereof and the series of adjustments leading to
such Warrant Price.

ARTICLE 3. REPRESENTATIONS AND COVENANTS OF THE COMPANY.
           --------------------------------------------

  3.1 Representations and Warranties. The Company hereby represents and warrants
      ------------------------------
to the Holder that all Shares which may be issued upon the exercise of the
purchase right represented by this Warrant, and all securities, if any, issuable
upon conversion of the Shares,

                                      -4-
<PAGE>

shall, upon issuance, be duly authorized, validly issued, fully paid and
nonassessable, and free of any liens and encumbrances except for restrictions on
transfer provided for herein or under applicable federal and state securities
laws.

  3.2 Notice of Certain Events. If the Company proposes at any time (a) to
      ------------------------
declare any dividend or distribution upon its common stock, whether in cash,
property, stock, or other securities and whether or not a regular cash dividend;
(b) to effect any reclassification or recapitalization of common stock; or (c)
to merge or consolidate with or into any other corporation, or sell, lease,
license, or convey all or substantially all of its assets, or to liquidate,
dissolve or wind up; then, in connection with each such event, the Company shall
give Holder (1) at least 20 days prior written notice of the date on which a
record will be taken for such dividend or distribution (and specifying the date
on which the holders of common stock will be entitled thereto) or for
determining rights to vote, if any, in respect of the matters referred to in (b)
and (c) above; and (2) in the case of the matters referred to in (b) and (c)
above at least 20 days prior written notice of the date when the same will take
place (and specifying the date on which the holders of common stock will be
entitled to exchange their common stock for securities or other property
deliverable upon the occurrence of such event).

  3.3 Information. So long as the Holder holds this Warrant and/or any of the
      -----------
Shares, the Company shall deliver to the Holder (a) promptly, copies of all
notices or other written communications to which the Holder would be entitled if
it held the Shares as to which this Warrant was then exercisable and (b) such
other financial statements required under and in accordance with any loan
documents between Holder and the Company, or if there are no such requirements
or if the subject loan(s) are no longer are outstanding, then within 45 days
after the end of each of the first three quarters of each fiscal year, the
Company's quarterly, unaudited financial statements.

  3.4 Registration Rights. The Common Stock issuable upon conversion of the
      --------------------
Shares, shall be entitled to "piggyback" registration rights in accordance with
the terms of the Investor Rights Agreement, dated as of ______________, between
the Company and its investors (the "Investor Rights Agreement" -- a true copy of
which has been furnished by the Company to the Holder) and by accepting this
Warrant, Holder agrees to be subject to corresponding obligations of the holders
of "piggyback" registration rights, including the market standoff obligations
(of up to 180 days) contained in the Investor Rights Agreement. Upon the
exercise of this Warrant, the Company will use reasonable best efforts to allow
Holder to become a party to the Investor Rights Agreement solely for purposes of
enabling Holding to obtain the "piggyback" registration rights described in the
preceding paragraph.

                                      -5-
<PAGE>

ARTICLE 4. MISCELLANEOUS.
           -------------

  4.1 Term: Notice of Expiration. This Warrant is exercisable, in whole or in
      --------------------------
part, at any time and from time to time on or before the Expiration Date set
forth above. The Company shall give Holder notice of Holder's right to exercise
this Warrant in the form attached as Appendix 2 not more than 90 days and not
less than 15 days before the Expiration Date and, in the case of an Acquisition
to which the provise of Section 1.7.2 shall be applicable, 15 days notice of
such Acquisition. If the notice is not so given, the Expiration Date shall
automatically be extended until 30 days after the date the Company delivers the
notice to Holder.

  4.2 Legends. This Warrant and the Shares (and the securities issuable,
      -------
directly or indirectly, upon conversion of the Shares, if any) shall be
imprinted with a legend in substantially the following form:

      THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS
    AMENDED, OR ANY STATE SECURITIES LAWS, AND MAY NOT BE SOLD, PLEDGED OR
    OTHERWISE TRANSFERRED EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION THEREOF
    UNDER SUCH ACT OR PURSUANT TO RULE 144 OR AN OPINION OF COUNSEL REASONABLY
    SATISFACTORY TO THE CORPORATION AND ITS COUNSEL THAT SUCH REGISTRATION IS
    NOT REQUIRED.

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

  4.4 Transfer Procedure. Subject to the provisions of Section 4.3 Holder may
      ------------------
transfer all or part of this Warrant or the Shares issuable upon exercise of
this Warrant (or the securities issuable, directly or indirectly, upon
conversion of the Shares, if any) at any time to Silicon Valley Bancshares or
The Silicon Valley Bank Foundation, or, to any other transferee acceptable to
the Company (which acceptance shall not be unreasonably withheld or delayed) by
giving the Company notice of the portion of the Warrant being transferred
setting forth the

                                      -6-
<PAGE>

name, address and taxpayer identification number of the transferee and
surrendering this Warrant to the Company for reissuance to the transferee(s)
(and Holder if applicable). Unless the Company is filing financial information
with the SEC pursuant to the Securities Exchange Act of 1934, the Company shall
have the right to refuse to transfer any portion of this Warrant to any person
who directly competes with the Company.

  4.5 Notices. All notices and other communications from the Company to the
      -------
Holder, or vice versa, shall be deemed delivered and effective when given
personally or mailed by first-class registered or certified mail, postage
prepaid, or by overnight courier, at such address as may have been furnished to
the Company or the Holder, as the case may be, in writing by the Company or such
holder from time to time.

  4.6 Waiver. This Warrant and any term hereof may be changed, waived,
      ------
discharged or terminated only by an instrument in writing signed by the party
against which enforcement of such change, waiver, discharge or termination is
sought.

  4.7 Attorneys Fees. In the event of any dispute between the parties concerning
      --------------
the terms and provisions of this Warrant, the party prevailing in such dispute
shall be entitled to collect from the other party all costs incurred in such
dispute, including reasonable attorneys' fees.

                                      -7-
<PAGE>

  4.8. Governing Law. This Warrant shall be governed by and construed in
       -------------
accordance with the laws of the State of California, without giving effect to
its principles regarding conflicts of law.

                              "COMPANY"

                              PLUMTREE SOFTWARE, INC., a
                              California corporation

                              By: /s/ PIERRE LAMOND
                              -------------------------

                              Name:  Pierre Lamond
                              -------------------------
                              (Print)

                              Title: Chairman of the Board, President or
                                     Vice President

                              By: /s/ GLENN KELMAN
                              -------------------------

                              Name:  Glenn Kelman
                              -------------------------
                              (Print)

                              Title:  Chief Financial Officer, Secretary,
                                      Assistant Treasurer or Assistant
                                      Secretary

                                      -8-<PAGE>

                                                                     EXHIBIT 4.5

THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER
THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE SOLD, PLEDGED, OR
OTHERWISE TRANSFERRED WITHOUT AN EFFECTIVE REGISTRATION THEREOF UNDER SUCH ACT
OR PURSUANT TO RULE 144 OR AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE
CORPORATION AND ITS COUNSEL, THAT SUCH REGISTRATION IS NOT REQUIRED.

                           WARRANT TO PURCHASE STOCK

Corporation: PLUMTREE SOFTWARE, INC., a California corporation (the "Company")

Number of Shares: (i) 105,000 divided by Fair Market Value (as defined below) if
the Obligations of the Company under and as defined in that certain Loan and
Security Agreement, dated as of the Issue Date (as defined below) (the "Loan
Agreement"), between the Company and Holder (as defined below) are repaid in
full within 90 days following the Issue Date or (ii) 120,000 divided by Fair
Market Value if the Obligations are repaid in full after 90 days following the
Issue Date.

Class of Stock: the Company's Series D Preferred Stock to be authorized and sold
in its next venture financing (the "Shares").

Initial Exercise Price: Fair Market Value (as used herein, the term "Fair Market
Value" means (i) the per share sale price of the Company's Series C Preferred
Stock or (ii) the per share sale price of the Company's Series D Preferred Stock
if the closing for the issue and sale thereof occurs within 90 days of the Issue
Date).

Issue Date: April 2, 1999

Expiration Date: The fifth anniversary of the Issue Date.

     THIS WARRANT CERTIFIES THAT, for the agreed upon value of $1.00 and for
other good and valuable consideration, SILICON VALLEY BANK ("Holder") is
entitled to purchase the number of fully paid and nonassessable Shares of the
Company at the Initial Exercise Price per Share as set forth above and as
adjusted pursuant to Article 2 of this Warrant (the "Warrant Price"), subject
to the provisions and upon the terms and conditions set forth in this Warrant.

                                      -1-
<PAGE>

ARTICLE 1. EXERCISE.
           --------

     1.1  Method of Exercise.  Holder may exercise his Warrant by delivering a
          ------------------
duly executed Notice of Exercise in substantially the form attached as Appendix
1 to the principal office of the Company. Unless Holder is exercising the
conversion right set forth in Section 1.2, Holder shall also deliver to the
Company a check for the aggregate Warrant Price for the Shares being purchased.

     1.2  Conversion Right.  In lieu of exercising this Warrant as specified in
          ----------------
Section 1.1, Holder may convert this Warrant, in whole but not in part, into a
number of Shares determined by dividing (a) the aggregate fair market value of
the Shares or other securities otherwise issuable upon exercise of this Warrant
minus the aggregate Warrant Price of such Shares by (b) the fair market value of
one Share.  The fair market value of the Shares shall be determined pursuant to
Section 1.4.

     1.3  (Intentionally Omitted)

     1.4  Fair Market Value.  If the Shares are traded in a public market, the
          -----------------
fair market value of the Shares shall be the average of the closing prices of
the Shares (or the closing price of the Company's stock into which the Shares
are convertible) reported for the five business days immediately before Holder
delivers its Notice of Exercise to the Company, or if there have been no sales
on any such business day, the average of the highest bid and lowest asked price
at the end of such business day. If the Shares are not traded in a public
market, the Board of Directors of the Company shall determine fair market value.
The foregoing notwithstanding, if Holder advises the Board of Directors in
writing that Holder disagrees with such determination, then the Company and
Holder shall promptly agree upon a reputable investment banking firm to
undertake such valuation.  If the valuation of such investment banking firm is
greater than that determined by the Board of Directors, then all fees and
expenses of such investment banking firm shall be paid by the Company. In all
other circumstances, such fees and expenses shall be paid by Holder.

     1.5  (Intentionally Omitted)

     1.6  Replacement of Warrants.  On receipt of evidence reasonably
          -----------------------
satisfactory to the Company of the loss, theft, destruction or mutilation of
this Warrant and, in the case of loss, theft or destruction, on delivery of an
indemnity agreement reasonably satisfactory in form and amount to the Company
or, in the case of mutilation, on surrender and cancellation of this Warrant,
the Company at its expense shall execute and deliver, in lieu of this Warrant, a
new warrant of like tenor.

     1.7  Repurchase on Sale, Merger, or Consolidation of the Company
          -----------------------------------------------------------

          1.7.1.    "Acquisition".  For the purpose of this Warrant,
                    -------------
     "Acquisition" means any sale, license, or other disposition of all or
     substantially all of the assets of the Company,

                                      -2-
<PAGE>

     or any reorganization, consolidation, or merger of the Company where the
     holders of the Company's securities before the transaction beneficially own
     less than 50% of the outstanding voting securities of the surviving entity
     after the transaction.

          1.7.2.    Assumption of Warrant. Upon the closing of any Acquisition,
                    ---------------------
     the successor entity shall assume the obligations of this Warrant, and this
     Warrant shall be exercisable for the same securities, cash, and property as
     would be payable for the Shares issuable upon exercise of the unexercised
     portion of this Warrant as if such Shares were outstanding on the record
     date for the Acquisition and subsequent closing, and the Warrant Price
     shall be adjusted accordingly; provided that if pursuant to such
                                    --------
     Acquisition the entire outstanding class of the Shares issuable upon
     exercise of the unexercised portion of this Warrant are canceled and the
     total consideration payable to the holders of such class of Shares consists
     entirely of cash, then, upon payment to the holder of this Warrant of an
     amount equal to the amount such holder would receive if such holder held
     the Shares issuable upon exercise of the unexercised portion of this
     Warrant and such Shares were outstanding on the record date for the
     Acquisition less the aggregate Warrant Price of such Shares, this Warrant
                 ----
     shall be canceled.

ARTICLE 2. ADJUSTMENTS TO THE SHARES.
           -------------------------

     2.1  Stock Dividends, Splits, Etc.  If the Company declares or pays a
          ----------------------------
dividend on its common stock (or the Shares if the Shares are securities other
than common stock) payable in common stock, or other securities, subdivides the
outstanding common stock into a greater amount of common stock, or, if the
Shares are securities other than common stock subdivides the Shares in a
transaction that increases the amount of common stock into which the Shares are
convertible, then upon exercise of this Warrant, for each Share acquired, Holder
shall receive, without cost to Holder, the total number and kind of securities
to which Holder would have been entitled had Holder owned the Shares of record
as of the date the dividend or subdivision occurred.

     2.2  Reclassification, Exchange or Substitution.  Except in the case of an
          ------------------------------------------
Acquisition to which the provisions of Section 1.7 are applicable, upon any
reclassification, exchange, substitution, or other event that results in a
change of the number and/or class of the securities issuable upon exercise or
conversion of this Warrant, Holder shall be entitled to receive, upon exercise
or conversion of this Warrant, the number and kind of securities and property
that Holder would have received for the Shares if this Warrant had been
exercised immediately before such reclassification, exchange, substitution, or
other event. The Company or its successor shall promptly issue to Holder a new
Warrant for such new securities or other property. The new Warrant shall provide
for adjustments which shall be as nearly equivalent as may be practicable to the
adjustments provided for in this Article 2 including, without limitation,
adjustments to the Warrant Price and to the number of securities or property
issuable upon exercise of the new Warrant. The provisions of this Section 2.2
shall similarly apply to successive reclassifications, exchanges, substitutions,
or other events.

                                      -3-
<PAGE>

     2.3  Adjustments for Combinations, Etc.  If the outstanding Shares are
          ---------------------------------
combined or consolidated, by reclassification or otherwise, into a lesser number
of shares, the Warrant Price shall be proportionately increased and the number
of Shares as to which this warrant is exercisable shall be proportionately
decreased.

     2.4  Adjustments for Diluting Issuances.  The Shares shall have the same
          ----------------------------------
dilution and other protections afforded to the outstanding securities of the
same class under the provisions of the Company's Amended and Restated Articles
of Incorporation (the "Provisions"), and for the purpose of the protections
provided under the Provisions, the Shares shall be deemed to be issued and
outstanding on and after the Issue Date.

     2.5  No Impairment.  The Company shall not, by amendment of its Articles of
          -------------
Incorporation or through a reorganization, transfer of assets, consolidation,
merger, dissolution, issue, or sale of securities or any other voluntary action,
avoid or seek to avoid the observance or performance of any of the terms to be
observed or performed under this Warrant by the Company, but shall at all times
in good faith assist in carrying out of all the provisions of this Article 2 and
in taking all such action as may be necessary or appropriate to protect Holder's
rights under this Article 2 against impairment.

     2.6  Fractional Shares.  No fractional Shares shall be issuable upon
          -----------------
exercise or conversion of the Warrant and the number of Shares to be issued
shall be rounded down to the nearest whole Share. If a fractional share interest
arises upon any exercise or conversion of the Warrant, the Company shall
eliminate such fractional share interest by paying Holder an amount computed by
multiplying the fractional interest by the fair market value of a full Share.

     2.7  Certificate as to Adjustments.  Upon each adjustment of the Warrant
          -----------------------------
Price, the Company at its expense shall promptly compute such adjustment and
furnish Holder with a certificate of its Chief Financial Officer setting forth
such adjustment and the facts upon which such adjustment is based. The Company
shall, upon written request, furnish Holder a certificate setting forth the
Warrant Price in effect upon the date thereof and the series of adjustments
leading to such Warrant Price.

ARTICLE 3.  REPRESENTATIONS AND COVENANTS OF THE COMPANY.
            --------------------------------------------

     3.1  Representations and Warranties.  The Company hereby represents and
          ------------------------------
warrants to the Holder that all Shares which may be issued upon the exercise of
the purchase right represented by this Warrant, and all securities, if any,
issuable upon conversion of the Shares, shall, upon issuance, be duly
authorized, validly issued, fully paid and nonassessable, and free of any liens
and encumbrances except for restrictions on transfer provided for herein or
under applicable federal and state securities laws.

     3.2  Notice of Certain Events.  If the Company proposes at any time (a) to
          ------------------------
declare any dividend or distribution upon its common stock, whether in cash,
property, stock, or other securities and whether or not a regular cash dividend;
(b) to effect any reclassification or

                                      -4-
<PAGE>

recapitalization of common stock; or (c) to merge or consolidate with or into
any other corporation, or sell, lease, license, or convey all or substantially
all of its assets, or to liquidate, dissolve or wind up; then, in connection
with each such event, the Company shall give Holder (1) at least 20 days prior
written notice of the date on which a record will be taken for such dividend or
distribution (and specifying the date on which the holders of common stock will
be entitled thereto) or for determining rights to vote, if any, in respect of
the matters referred to in (b) and (c) above; and (2) in the case of the matters
referred to in (b) and (c) above at least 20 days prior written notice of the
date when the same will take place (and specifying the date on which the holders
of common stock will be entitled to exchange their common stock for securities
or other property deliverable upon the occurrence of such event).

     3.3  Information.  So long as the Holder holds this Warrant and/or any of
          -----------
the Shares, the Company shall deliver to the Holder (a) promptly, copies of all
notices or other written communications to which the Holder would be entitled if
it held the Shares as to which this Warrant was then exercisable and (b) such
other financial statements required under and in accordance with any loan
documents between Holder and the Company, or if there are no such requirements
or if the subject loan(s) are no longer are outstanding, then within 45 days
after the end of each of the first three quarters of each fiscal year, the
Company's quarterly, unaudited financial statements.

     3.4  Registration Rights.  The Common Stock issuable upon conversion of the
          -------------------
Shares, shall be entitled to "piggyback" registration rights in accordance with
the terms of the Investor Rights Agreement, dated as of _________ , between the
Company and its investors (the "Investor Rights Agreement" -- a true copy of
which has been furnished by the Company to the Holder) and by accepting this
Warrant, Holder agrees to be subject to corresponding obligations of the holders
of "piggyback" registration rights, including the market standoff obligations
(of up to 180 days) contained in the Investor Rights Agreement. Upon the
exercise of this Warrant, the Company will use reasonable best efforts to allow
Holder to become a party to the Investor Rights Agreement solely for purposes of
enabling Holding to obtain the "piggyback" registration rights described in the
preceding paragraph.

ARTICLE 4.  MISCELLANEOUS.
            -------------

     4.1  Term; Notice of Expiration.  This Warrant is exercisable, in whole or
          --------------------------
in part, at any time and from time to time on or before the Expiration Date set
forth above. The Company shall give Holder notice of Holder's right to exercise
this Warrant in the form attached as Appendix 2 not more than 90 days and not
less than 15 days before the Expiration Date and, in the case of an Acquisition
to which the proviso of Section 1.7.2 shall be applicable, 15 days notice of
such Acquisition. If the notice is not so given, the Expiration Date shall
automatically be extended until 30 days after the date the Company delivers the
notice to Holder.

                                      -5-
<PAGE>

     4.2  Legends. This Warrant and the Shares (and the securities issuable,
          -------
directly or indirectly, upon conversion of the Shares, if any) shall be
imprinted with a legend in substantially the following form:

          THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF
     1933, AS AMENDED, OR ANY STATE SECURITIES LAWS, AND MAY NOT BE SOLD,
     PLEDGED OR OTHERWISE TRANSFERRED EXCEPT PURSUANT TO AN EFFECTIVE
     REGISTRATION THEREOF UNDER SUCH ACT OR PURSUANT TO RULE 144 OR AN OPINION
     OF COUNSEL REASONABLY SATISFACTORY TO THE CORPORATION AND ITS COUNSEL THAT
     SUCH REGISTRATION IS NOT REQUIRED.

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

     4.4  Transfer Procedure.  Subject to the provisions of Section 4.3 Holder
          ------------------
may transfer all or part of this Warrant or the Shares issuable upon exercise of
this Warrant (or the securities issuable, directly or indirectly, upon
conversion of the Shares, if any) at any time to Silicon Valley Bancshares or
The Silicon Valley Bank Foundation, or, to any other transferee acceptable to
the Company (which acceptance shall not be unreasonably withheld or delayed) by
giving the Company notice of the portion of the Warrant being transferred
setting forth the name, address and taxpayer identification number of the
transferee and surrendering this Warrant to the Company for reissuance to the
transferee(s) (and Holder if applicable). Unless the Company is filing financial
information with the SEC pursuant to the Securities Exchange Act of 1934, the
Company shall have the right to refuse to transfer any portion of this Warrant
to any person who directly competes with the Company.

     4.5  Notices.  All notices and other communications from the Company to the
          -------
Holder, or vice versa, shall be deemed delivered and effective when given
personally or mailed by first-class registered or certified mail, postage
prepaid, or by overnight courier, at such address as may have been furnished to
the Company or the Holder, as the case may be, in writing by the Company or such
holder from time to time.

                                      -6-
<PAGE>

     4.6  Waiver.  This Warrant and any term hereof may be changed, waived,
          ------
discharged or terminated only by an instrument in writing signed by the party
against which enforcement of such change, waiver, discharge or termination is
sought.

     4.7  Attorneys Fees.  In the event of any dispute between the parties
          --------------
concerning the terms and provisions of this Warrant, the party prevailing in
such dispute shall be entitled to collect from the other party all costs
incurred in such dispute, including reasonable attorneys' fees.

     4.8  Governing Law.  This Warrant shall be governed by and construed in
          -------------
accordance with the laws of the State of California, without giving effect to
its principles regarding conflicts of law.

                                       "COMPANY"

                                       PLUMTREE SOFTWARE, INC.,
                                       a California corporation

                                       By: /s/JOHN KUNZE
                                       -----------------------------------
                                       Name: John Kunze
                                       -----------------------------------
                                       (Print)
                                       Title:      CEO

                                               Chairman of the Board, President
                                               or Vice President

                                       By: /s/MARSHALL SMITH
                                       -----------------------------------
                                       Name: Marshall Smith
                                       -----------------------------------
                                       (Print)
                                       Title:
                                               Chief Financial Officer,
                                               Secretary, Assistant Treasurer or
                                               Assistant Secretary

                                      -7-

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