Document:

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                                                                    EXHIBIT 10.4

This Warrant has not been registered under the Securities Act of 1933, as
amended, 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 an opinion of counsel reasonably
satisfactory to DigitalWork.com, Inc. that such registration is not required.

                     SERIES D CONVERTIBLE PREFERRED STOCK
                               PURCHASE WARRANT

Warrant No. Attractor                             Number of Shares _____________

                             DIGITALWORK.COM, INC.

     1.   Issuance.  This Warrant is issued to Attractor Institutional LP by
          --------
DigitalWork.com, Inc., a Delaware corporation (hereinafter with its successors
called the "Company").

     2.   Exercise of Warrant to Purchase Series D Preferred Stock.  Subject to
          --------------------------------------------------------
the terms and conditions hereinafter set forth, the registered holder of this
Warrant (the "Holder"), commencing on the date set forth on the signature page
hereof, is entitled upon surrender of this Warrant with the subscription form
annexed hereto duly executed, at the office of the Company, 230 West Monroe
Street, Suite 1950, Chicago, Illinois  60606, or such other office as the
Company shall notify the Holder of in writing, to purchase from the Company that
certain number of shares as determined in the formula set forth in Section 2 of
that certain Warrant Purchase Agreement among the Company and the Holder, among
others, dated December 2, 1999, fully paid and nonassessable shares of Series D
Convertible Preferred Stock of the Company, par value $0.005 per share ("Series
D Preferred Stock") at $8.36 per share (the "Purchase Price"), which price is
identical to the purchase price per share of Series D Preferred Stock the
Company sold to the Purchasers set forth in that certain Series D Preferred
Stock Purchase Agreement among the Company and the Purchasers dated as of
December 2, 1999 (the "Purchase Agreement"),.

     3.   Payment of Purchase Price.
          -------------------------

          (a)  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, (iii)
through delivery by the Holder to the Company of other securities issued by the
Company, with such securities being credited against the Purchase Price in an
amount equal to the Fair Market Value thereof, as determined below.

          (b)  The Holder may elect to receive, without the payment by the
Holder of any additional consideration, shares 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

                                                                     Page 1 of 6
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annexed hereto duly executed, at the office of the Company. Thereupon, the
Company shall issue to the Holder such number of fully paid and nonassessable
shares of Series D Preferred Stock as is computed using the following formula:

                                  X = Y (A-B)
                                      -------
                                       A

          where

          X =  the number of shares to be issued to the Holder pursuant to this
          Section 3(b).

          Y =  the number of shares covered by this Warrant in respect of which
          the net issue election is made pursuant to this Section 3(b).

          A =  the Fair Market Value of one share of Series D Preferred Stock at
          the time the net issue election is made pursuant to this Section 3(b).

          B =  the Purchase Price.

          Where "Fair Market Value" means:
                 -----------------

               (i)    If shares of Common Stock are then listed or admitted to
trading on any national securities exchange or traded on any national market
system, the average of the daily closing prices for the five (5) trading days
before such date, excluding any trades which are not bona fide, arm's length
transactions multiplied by the number of shares of Common Stock a share of
Series D Preferred would then convert into. The closing price for each day shall
be the last sale price on such date or, if no such sale takes place on such
date, the average of the closing bid and asked prices on such date, in each case
as officially reported on the principal national securities exchange or national
market system on which such shares are then listed, admitted to trading or
traded;

               (ii)   If no shares of Common Stock are then listed or admitted
to trading on any national securities exchange or traded on any national market
for the five (5) trading days before such date, the average of the reported
closing bid and asked prices thereof on such date in the over-the-counter market
as shown by the National Association of Securities Dealers automated quotation
system or, if such shares are not then quoted in such system, as published by
the National Quotation Bureau, Incorporated or any similar successor
organization, and in either case as reported by any member firm of the New York
Stock Exchange selected by Holder multiplied by the number of shares of Common
Stock a share of Series D Preferred would then convert into;

               (iii)  If no shares of Common Stock are then listed or admitted
to trading on any national exchange or traded on any national market system, if
no closing bid and asked prices thereof are then so quoted or published in the
over-the-counter market for the five (5) trading days before such date, the Fair
Market Value of a share of Series D Preferred shall be a determined in good
faith by the mutual agreement of the parties.

                                                                     Page 2 of 6
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     4.   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.

     5.   Issuance Date.  The person or persons in whose name or names any
          -------------
certificate representing shares of Series D 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.

     6.   Expiration Date; Automatic Exercise.  This Warrant shall expire at the
          -----------------------------------
close of business on December 2, 2004 (i.e. five years from the execution of the
Purchase Agreement), and shall be void thereafter.

     7.   Reserved Shares; Valid Issuance. The Company covenants that it will at
          -------------------------------
all times from and after the date hereof take such action as is necessary to
reserve and keep available such number of its authorized shares of Series D
Preferred Stock and Common Stock, $0.005 par value (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 Series D Preferred Stock receivable upon
such exercise.  The Company further covenants that such shares as may be issued
pursuant to such exercise and 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.

     8.   Stock Dividends.  If after the date hereof the Company shall subdivide
          ---------------
the Series D Preferred Stock, by split-up or otherwise, or combine the Series D
Preferred Stock, or issue additional shares of Series D Preferred Stock in
payment of a stock dividend on the Series D Preferred Stock, the number of
shares 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.

     9.   Mergers and Reclassifications. If after the date hereof there shall be
          -----------------------------
any reclassification, capital reorganization or change of the Series D Preferred
Stock (other than as a result of a subdivision, combination or stock dividend
provided for in Section 8 hereof), or any consolidation of the Company with, or
merger of the Company into, another corporation or other business organization
(other than a consolidation or merger in which the Company is the continuing
corporation and which does not result in any reclassification or change of the
outstanding Series D 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, then, as a condition of such reclassification,
reorganization, change, consolidation, merger, sale or conveyance, 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
reclassification, reorganization, change, consolidation, merger, sale or
conveyance by a holder of the number of shares of Series D Preferred Stock which
might have been purchased by the Holder immediately prior to such
reclassification, reorganization, change,

                                                                     Page 3 of 6
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consolidation, merger, sale or conveyance (or, if there are no holders of Series
D Preferred Stock at such time, by a holder of the number of shares of Common
Stock which might have been acquired by the Holder immediately prior to such
reclassification, reorganization, change, consolidation, merger, sale or
conveyance upon the exercise of this Warrant in full and the conversion into
shares of Common Stock of all shares of Series D Preferred Stock receivable upon
such exercise), 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) shall thereafter be
applicable in relation to any shares of stock or other securities and property
thereafter deliverable upon exercise hereof.

     10.  Fractional Shares.  In no event shall any fractional share of Series D
          -----------------
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 11, be entitled to receive a fractional share of Series D Preferred
Stock, then the Company shall issue the next higher number of full shares of
Series D Preferred Stock, issuing a full share with respect to such fractional
share.

     11.  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 or otherwise acquire 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 and in each such event the Company will mail or cause to be mailed to the
Holder a notice specifying (i) the date on which any such record is to be taken
for the purpose of such dividend, distribution or right, and stating the amount
and character of such dividend, distribution or right, or (ii) the date on which
any such reclassification, reorganization, consolidation, merger, sale or
conveyance, dissolution, liquidation or winding-up is to take place, and the
time, if any is to be fixed, as of which the holders of record in respect of
such event are to be determined.  Such notice shall be mailed at least 20 days
prior to the date specified in such notice on which any such action is to be
taken.

     12.  Other Warrants.  This Warrant is one of a series of warrants
          --------------
(collectively, the "Warrants") that were issued by the Company to members of the
Attractor Group pursuant to the Purchase Agreement.

     13.  Warrant Register; Transfers, Etc.
          ---------------------------------

          (a)  The Company will maintain a register containing the names and
addresses of the registered holders of the Warrants.  The Holder may change its
address as shown on the

                                                                     Page 4 of 6
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warrant register by written notice to the Company requesting such change. 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 its address as
shown on the warrant register.

          (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 hereof properly endorsed, 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 Series D
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 evidence reasonably satisfactory to the
Company of the loss, theft or destruction of such Warrant (including a
reasonably detailed affidavit with respect to the circumstances of any loss,
theft or destruction) and of indemnity reasonably satisfactory to the Company,
provided, however, that so long as Holder is the registered holder of this
Warrant, no indemnity shall be required other than its written agreement to
indemnify the Company against any loss arising from the issuance of such new
warrant.

     14.  Registration Rights Agreement, Stockholders Agreement and Purchase
          ------------------------------------------------------------------
Agreement.  Each of the Holder and the Company covenants to execute, and become
---------
a party to, the Amended and Restated Registration Rights Agreement among the
Company and the Purchasers of the Series D Preferred Stock and the Company's
Series C Convertible Preferred Stock ("Series C Preferred Stock") dated December
2, 1999 (pursuant to which the holder of this Warrant will become an Investor
thereunder and the shares of Series D Preferred Stock purchased pursuant to this
Warrant shall be Registrable Stock and Series D Registrable Stock (each as
defined therein)) and the Amended and Restated Stockholders Agreement among the
Company and the Purchasers of the Series D Preferred Stock and the Series C
Preferred Stock dated December 2, 1999, with respect to the shares of Series D
Preferred Stock subject to this Warrant.  The holder of this Warrant shall be
entitled to the benefits and subject to the obligations set forth in the
Purchase Agreement with respect to the shares of Series D Preferred Stock it
purchases pursuant to this Warrant.

     15.  No Impairment.  The Company will not, by amendment of its Articles of
          -------------
Incorporation, as amended, 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 or 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.

                                                                     Page 5 of 6
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     16.  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
Delaware.

     17.  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. All of the rights of a
holder of this Warrant may only be transferred by the holder to the following:
(i) if holder is a partnership, any partner or retired partner of such
Purchaser, (ii) if the holder is an individual, any family member of or trust
for the benefit of such holder, (iii) if the holder is a corporation, any
shareholder of such holder, (iv) if the holder is a limited liability company,
to a member of such holder, or (v) any transferee who acquires at least $500,000
of Series D Preferred; provided, that, such transfer otherwise complies with all
applicable state and federal securities laws.  For purposes of determining the
availability of any rights under this Warrant, all shares of Series D Preferred
held or acquired by affiliated persons or persons under common management shall
be aggregated together and treated as one such holder.

Dated:  December 31, 1999         DigitalWork.com, Inc.,
                                  A Delaware Corporation

                                  By: __________________________________________
                                  Name:   Craig A. Terrill
Attest:                           Title:  President and Chief Operating Officer

__________________________________

                                                                     Page 6 of 6
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                                 Subscription

To: ________________________________       Date: _______________________________

     The undersigned hereby subscribes for ______________ shares of Series D
Preferred Stock covered by this Warrant. The undersigned hereby represents and
warrants to the Company all of the representation and warranties set forth in
Article III of that certain Series D Convertible Preferred Stock Purchase
Agreement dated as of December 2, 1999 as though the same were full set forth
herein. 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 3(b) to surrender the right to
purchase _______ shares of Eligible Preferred Stock pursuant to this Warrant.
The certificate(s) for the shares issuable upon such net issue election shall be
issued in the name of the undersigned or as otherwise indicated below.

                                        ________________________________________
                                        Signature

                                        ________________________________________
                                        Name for Registration

                                        ________________________________________
                                        Mailing Address
<PAGE>

                                  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:

_____________________________<PAGE>

                                                                    EXHIBIT 10.6

THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE BEEN ACQUIRED FOR INVESTMENT
AND HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933 AS AMENDED.  THESE
SECURITIES MAY NOT BE SOLD, OFFERED FOR SALE, PLEDGED OR HYPOTHECATED IN THE
ABSENCE OF AN EFFECTIVE REGISTRATION STATEMENT AS TO THE SECURITIES UNDER SAID
ACT OR LAWS OR AN OPINION OF COUNSEL SATISFACTORY TO THE CORPORATION THAT SUCH
REGISTRATION IS NOT REQUIRED.

                             DIGITALWORK.COM, INC.

                          STOCK SUBSCRIPTION WARRANT

                                               December 29, 1999

1.   General.
     -------

          (a)  THIS CERTIFIES that, for value received, AMERICA ONLINE, INC.
("AOL"), or assigns, is entitled to subscribe for and purchase from
DIGITALWORK.COM, INC., a Delaware corporation (the "Corporation"), at any time
or from time to time during the period (the "Exercise Period") commencing with
the date hereof and ending on the earlier of (i) the third (3rd) anniversary of
the Corporation's initial firmly written public offering of Common Stock, $0.005
par value (the "Common Stock") of the Corporation (the "IPO") and (ii) the fifth
(5th) anniversary of the date hereof, on the terms and subject to the provisions
hereinafter set forth, up to 276,000 of shares (subject to adjustment as
provided herein) of fully paid and non-assessable shares of Series D Preferred
Stock, $0.005 par value, of the Corporation, at a price per share (the "Warrant
Price") of $8.36 (subject to adjustment as provided herein) or in the event the
Preferred Stock shall prior to exercise or exchange of this Warrant have been
converted into Common Stock, $0.005 par value (the "Common Stock") of the
Corporation as a result of an automatic conversion event (as defined in Article
IV, Section 3.2 of the Amendment of the Amended and Restated Certificate of
Incorporation of the Corporation), that number of shares of Common Stock into
which such number of shares of Preferred Stock is converted ("Mandatory
Conversion Event") at any time or from time to time during the Exercise Period.

The shares of capital stock of the Corporation issuable upon exercise or
exchange of this Warrant are sometimes hereinafter referred to as the "Warrant
Shares," and, in connection therewith, all references herein to Warrant Shares
shall mean Preferred Stock until the occurrence of a Mandatory Conversion Event,
and upon and at all times after, the occurrence of a Mandatory Conversion Event,
shall mean Common Stock.

2.   Exercise of Warrant.
     -------------------

          The rights represented by this Warrant may be exercised by the holder
hereof in whole or in part, at any time or from time to time during the Exercise
Period, by the surrender of
<PAGE>

this Warrant (properly endorsed) at the office of the Corporation at 230 West
Monroe Street, Suite 1950, Chicago, Illinois 60606, or at such other agency or
office of the Corporation in the United States of America as it may designate by
notice in writing to the holder hereof at the address of such holder appearing
on the books of the Corporation, and by payment (either in cash, by check, by
cancellation of indebtedness and/or in shares of capital stock of the
Corporation valued at Fair Market Value (as hereinafter defined) on the date of
such exercise) to the Corporation of the Warrant Price for each Warrant Share
being purchased. In the event of the exercise of the rights represented by this
Warrant, a certificate or certificates for the Warrant Shares so purchased,
registered in the name of the holder, and if this Warrant shall not have been
exercised for all of the Warrant Shares, a new Warrant, registered in the name
of the holder hereof, of like tenor to this Warrant, shall be delivered to the
holder hereof within a reasonable time, not exceeding ten days, after the rights
represented by this Warrant shall have been so exercised. The person in whose
name any certificate for Warrant Shares is issued upon exercise of this Warrant
shall for all purposes be deemed to have become the holder of record of such
shares on the date on which the Warrant was surrendered and payment of the
Warrant Price and any applicable taxes was made, irrespective of the date of
delivery of such certificate, except that, if the date of such surrender and
payment is a date when the stock transfer books of the Corporation are closed,
such person shall be deemed to have become the holder of such shares at the
close of business on the next succeeding date on which the stock transfer books
are open.

3.   Exchange of Warrant.
     -------------------
          (a)  In addition to, and independent of, the rights of the holder of
this Warrant set forth in Section 2 hereof, the holder hereof may at any time or
from time to time elect to receive, without the payment by the holder of any
additional consideration, that number of Warrant Shares determined as
hereinafter provided in this Section 3 by the surrender of this Warrant or any
portion hereof to the Corporation, accompanied by an executed Notice of Exchange
in substantially the form thereof attached hereto (the "Net Issue Election").
Thereupon, the Corporation shall issue to the holder hereof such number of fully
paid and nonassessable Warrant Shares as is computed using the following
formula:

                              X = Y (A-B)
                                  -------
                                     A

where X =  the number of Warrant Shares to be issued to the holder pursuant to
           this Section 3.

      Y =  the number of Warrant Shares covered by this Warrant in respect of
           which the Net Issue Election is made pursuant to this Section 3.

      A =  the Fair Market Value (as hereinafter defined) of one Warrant Share
           determined at the time the Net Issue Election is made pursuant to
           this Section 3 (the "Determination Date").

      B =  the Warrant Price in effect under this Warrant at the time the Net
           Issue Election is made pursuant to this Section 3.

                                       2
<PAGE>

For purposes of the above calculation, "Fair Market Value" of one Warrant Share
as of the Determination Date shall mean:

               (i)   if as a result of a Mandatory Conversion Event the Warrant
Shares mean Common Stock as set forth in Section 1, then (A) if the Common Stock
of the Corporation is not then traded on a national securities exchange, the
average of the closing prices quoted on the National Association of Securities
Dealers, Inc. Automated Quotation National Market System, if applicable, or the
average of the last bid and asked prices of the Common Stock quoted in the over-
the-counter-market or (B) if the Common Stock is then traded on a national
securities exchange, the average of the high and low prices of the Common Stock
listed on the principal national securities exchange on which the Common Stock
is so traded, in each case for the twenty (20) trading days immediately
preceding the Determination Date;

               (ii)  in the event of a Warrant Exchange in connection with a
Corporate Transaction, the value per share of Common Stock received or
receivable by each holder thereof (assuming, in the case of a sale of assets,
the Corporation is liquidated immediately following such sale and the
consideration paid to the Corporation is immediately distributed to its
stockholders); and

               (iii) in all other circumstances, the fair market value per share
of Common Stock as determined by (i) the Corporation's Board of Directors in
good faith after taking into consideration all factors it deems appropriate,
including, without limitation, recent sale and offer prices of the capital stock
of the Corporation in private transactions negotiated at arm's length, or (ii) a
nationally recognized independent investment banking firm jointly selected by
the Corporation and the holder of this Warrant or, if such selection cannot be
made within five business days after delivery of the Notice of Exchange referred
to above, by a nationally recognized independent investment banking firm
selected by the American Arbitration Association then obtaining, at the sole
discretion of AOL.

The closing of any Warrant Exchange shall take place at the offices of the
Corporation on the date specified in the Notice of Exchange (the "Exchange
Date"), which shall be not less than five and not more than 30 days after the
delivery of such Notice.  At such closing, the Corporation shall issue and
deliver to the holder or its designee a certificate or certificates for the
Warrant Shares to be issued upon such Warrant Exchange, registered in the name
of the holder or such designee, and if such Warrant Exchange shall not have been
for all Warrant Shares, a new Warrant, registered in the name of the holder, of
like tenor to this Warrant for the number of shares still subject to this
Warrant following such Warrant Exchange.

4.   Adjustment of Warrant Price.
     ---------------------------

          (a)  The Warrant Price and number of Warrant Shares shall be subject
to adjustment from time to time as follows:

               (i)  If, at any time during the Exercise Period, the number of
shares of Common Stock outstanding is increased by a stock dividend payable in
shares of Common

                                       3
<PAGE>

Stock or by a subdivision or split-up of shares of Common Stock, then, following
the record date fixed for the determination of holders of Common Stock entitled
to receive such stock dividend, subdivision or split-up, the Warrant Price shall
be appropriately decreased and the number of shares of Preferred Stock issuable
upon the exercise of this Warrant or the Common Stock issuable upon conversion
of the Preferred Stock shall be appropriately increased, in each case in
proportion to such increase in outstanding shares.

               (ii)  If, at any time during the Exercise Period, the number of
shares of Common Stock outstanding is decreased by a combination of the
outstanding shares of Common Stock, then, following the record date for such
combination, the Warrant Price shall be appropriately increased and the number
of shares of Preferred Stock issuable upon the exercise of this Warrant or the
Common Stock issuable upon conversion of the Preferred Stock shall be
appropriately decreased, in each case, in proportion to such decrease in
outstanding shares.

               (iii) All calculations under this Section 4 shall be made to the
nearest one tenth (1/10) of a cent or to the nearest one tenth (1/10) of a
share, as the case may be.

          (b)  Whenever the Warrant Price shall be adjusted as provided in this
Section 4 the Corporation shall forthwith file, at the office of the Corporation
or any transfer agent designated by the Corporation for the Common Stock, a
statement, signed by its chief financial officer, showing in detail the facts
requiring such adjustment and the adjusted Warrant Price.  The Corporation shall
also cause a copy of such statement to be sent by first-class certified mail,
return receipt requested, postage prepaid, to each holder of a Warrant at his or
its address appearing on the Corporation's records.  Where appropriate, such
copy may be given in advance and may be included as part of a notice required to
be mailed under the provisions set forth immediately below.

          (c)  In the event the Corporation shall propose to take any action of
the types described in Section 4(a)(i) or (ii) or Section 11, the Corporation
shall give notice to each holder of a Warrant in the manner set forth herein,
which notice shall specify the record date, if any, with respect to any such
action and the date on which such action is to take place.  Such notice shall
also set forth such facts with respect thereto as shall be reasonably necessary
to indicate the effect of such action (to the extent such effect may be known at
the date of such notice) on the Warrant Price then in effect and the number,
kind or class of shares or other securities or property which shall be delivered
or purchasable upon the occurrence of such action or deliverable upon exercise
of this Warrant.  In the case of any action which would require the fixing of a
record date, such notice shall be given at least 20 days prior to the date so
fixed, and in case of all other action, such notice shall be given at least 30
days prior to the taking of such proposed action.  Failure to give such notice,
or any defect therein, shall not affect the legality or validity of any such
action.

                                       4
<PAGE>

5.   Covenants as to Preferred Stock.
     --------------------------------

               (a)  The Corporation covenants and agrees that all shares of
Preferred Stock which may be issued upon the exercise of the rights represented
by this Warrant, and all shares of Common Stock which may be issued upon the
conversion of the Preferred Stock will, upon issuance, be validly issued, fully
paid and non-assessable and free from all taxes, liens and charges with respect
to the issuance thereof. The Corporation further covenants and agrees that the
Corporation will from time to time take all such action as may be requisite to
assure that the stated or par value per share of the Preferred Stock and the
Common Stock is at all times equal to or less than the then effective Warrant
Price per share of Preferred Stock issuable upon exercise of this Warrant. The
Corporation further covenants and agrees that the Corporation will at all times
have authorized and reserved, free from preemptive rights, a sufficient number
of (a) shares of its Preferred Stock to provide for the exercise of the rights
represented by this Warrant and (b) shares of Common Stock to provide for the
conversion of the Preferred Stock issuable upon exercise of this Warrant. The
Corporation further covenants and agrees that if any shares of capital stock to
be reserved for the purpose of the issuance of shares of Preferred Stock upon
the exercise of this Warrant require registration with or approval of any
governmental authority under any Federal or state law before such shares may be
validly issued or delivered upon exercise, then the Corporation will in good
faith and expeditiously as possible endeavor to secure such registration or
approval, as the case may be. If and so long as the Preferred Stock or Common
Stock issuable upon the exercise of the rights represented by this Warrant is
listed on any national securities exchange, the Corporation will, if permitted
by the rules of such exchange, list and keep listed on such exchange, upon
official notice of issuance, all shares of such capital stock.

               (b)  The Corporation further covenants and agrees that the holder
hereof will be entitled to the benefits of any adjustment prior to the exercise
hereof pursuant to any anti-dilution protection and any notice of adjustment of
the conversion price provided to the holders of Preferred Stock in accordance
with the Corporation's Certificate of Incorporation.

6.   No Shareholder Rights.
     ---------------------

               This Warrant shall not entitle the holder hereof to any voting
rights or other rights as a shareholder of the Corporation.

7.   Restrictions on Transfer.
     ------------------------

               The holder of this Warrant acknowledges that neither this Warrant
nor the Warrant Shares have been registered under the Securities Act of 1933, as
amended (the "Securities Act") and the holder of this Warrant agrees that no
sale, transfer, assignment, hypothecation or other disposition of this Warrant
or the Warrant Shares shall be made in the absence of (a) current registration
statement under the Securities Act as to this Warrant or the Warrant Shares and
the registration or qualification of this Warrant or the Warrant Shares under
any applicable state securities laws is then in effect or (ii) an opinion of
counsel reasonably satisfactory to the Corporation to the effect that such
registration or qualification is not required.

                                       5
<PAGE>

Each certificate or other instrument for Warrant Shares issued upon exercise of
this Warrant shall, if required under the Securities Act or the rules
promulgated thereunder, be imprinted with a legend substantially to the
foregoing effect.

8.   Representations and Warranties.
     ------------------------------

               (a)  The Corporation hereby represents and warrants to AOL as of
the date hereof:
                    (i)   The Corporation is a corporation duly organized,
validly existing and in good standing under the laws of the State of

                    (ii)  Delaware and has all requisite corporate power and
authority to carry on its business as now conducted and as proposed to be
conducted.

                    (iii) On the date hereof, the authorized capital stock of
     the Corporation consists of Sixty Two Million Five Hundred Twenty Nine
     Thousand One Hundred Forty Six (62,529,146) shares, such shares being
     divided into Forty One Million Six Hundred Thirty Three Thousand Seven
     Hundred Eighty Six (41,633,786) shares of Common Stock, par value $0.005
     per share, and Twenty Million Eight Hundred Ninety Five Thousand Three
     Hundred Sixty (20,895,360) shares of Preferred Stock, par value $0.005 per
     share, of which One Million Eight Hundred Sixty Six Thousand Six Hundred
     Seventy Two (1,866,672) shares are denominated Series A Preferred Stock
     ("Series A Preferred"), Two Million Three Hundred Seventy-Four Thousand
     (2,374,000) shares are denominated Series B Preferred Stock ("Series B
     Preferred"), Eleven Million Four Hundred Seventy One Thousand Two Hundred
     Seventy Six (11,471,276) shares are denominated Series C Preferred Stock
     ("Series C Preferred") and Five Million One Hundred Eighty Three Thousand
     Four Hundred Twelve (5,183,412) shares are denominated Series D Preferred
     Stock ("Series D Preferred"). On the date hereof, Three Million Eight
     Hundred Seventy Three Thousand Two Hundred Forty One (3,873,241) shares of
     Common Stock will be validly issued and outstanding, fully paid and
     nonassessable and One Million Eight Hundred Sixty Six Thousand Six Hundred
     Seventy Two (1,866,672) shares of Series A Preferred, Two Million Three
     Hundred Seventy Four Thousand (2,374,000) shares of Series B Preferred and
     Eleven Million Four Hundred Seventy One Thousand Two Hundred Seventy Six
     (11,471,276) shares of Series C Preferred and [Five Million One Hundred
     Eighty Three Thousand Four Hundred Twelve (5,183,412)] shares of Series D
     Preferred will be validly issued and outstanding, fully paid and
     nonassessable. The stockholders of record and holders of subscriptions,
     warrants, options, convertible securities, and other rights (contingent or
     other) to purchase or otherwise acquire equity securities of the Company,
     and the number of shares of Common stock and the number of such
     subscriptions, warrants, options, convertible securities, and other such
     rights held by each are as set forth on the attached Schedule I.
                                                          ----------

                    (iv)  All corporate action on the part of the Corporation,
     its board of directors, officers, and stockholders necessary for the
     authorization, execution and

                                       6
<PAGE>

     delivery of this Warrant and the performance of the Corporation of its
     obligations hereunder has been taken. This Warrant has been duly
     authorized, executed and delivered by the Corporation. This Warrant
     represents the valid and legally binding obligation of the Corporation,
     enforceable in accordance with its terms, except as limited by applicable
     bankruptcy, insolvency, reorganization, moratorium and other laws of
     general application affecting creditors' rights generally.

               (v)  The Corporation is not in violation of its certificate of
     incorporation or by-laws or in default in the performance or observance of
     any material obligation, agreement, covenant or condition contained in any
     Contract to which the Corporation is a party. The execution, delivery and
     performance by the Corporation of the Transaction Agreements, and the
     consummation by the Corporation of the transactions contemplated thereby
     will not (i) materially violate any provision of law, statute, rule or
     regulation, or any ruling, writ, injunction, order, judgment or decree of
     any court, administrative agency or other governmental body currently
     applicable to the Corporation or any of the properties or assets of the
     Corporation, (ii) materially conflict with or result in any breach of any
     of the terms, conditions or provisions of, or constitute (with due notice
     or lapse of time, or both) a default (or give rise to any right of
     termination, cancellation or acceleration) under any material Contract or
     (iii) violate the certificate of incorporation or the by-laws of the
     Corporation.

               (vi) The Warrant Shares, when issued, sold and delivered in
     accordance with the terms of this Warrant, will be duly and validly issued,
     fully paid and nonassessable, and will be free of any preemptive or similar
     rights.

          (b)  AOL hereby represents and warrants to the Corporation as follows:

               (i)  AOL is a corporation duly organized, validly existing and in
     good standing under the laws of the State of Delaware and has all requisite
     corporate power and authority to carry on its business as now conducted and
     as proposed to be conducted.

               (ii) All corporate action on the part of AOL, its board of
     directors, officers, and stockholders necessary for the authorization,
     execution and delivery of this Warrant and the performance of AOL of its
     obligations hereunder has been taken. This Warrant has been duly
     authorized, executed and delivered by AOL and represents the valid and
     legally binding obligation of AOL, enforceable in accordance with its
     terms, except as limited by applicable bankruptcy, insolvency,
     reorganization, moratorium and other laws of general application affecting
     creditor's rights generally.

               (iii) The Warrant and the Warrant Shares to be acquired on the
     exercise thereof (collectively, the "Securities") will be acquired by AOL
     for investment for its own account, not as a nominee or agent, and not with
     a view to the resale or distribution of any part thereof, and AOL has no
     present intention of selling, granting any participation in, or otherwise
     distributing the same. AOL does not have any contract,

                                       7
<PAGE>

     undertaking, agreement or arrangement with any person to sell, transfer or
     grant participations to any third person with respect to any of the
     Securities.

               (iv) AOL is an "accredited investor" within the meaning of Rule
     501 of Regulation D promulgated by the Securities and Exchange Commission,
     as presently in effect.

9.   Rights of the Holder.
     --------------------

          (a)  Anything contained herein to the contrary notwithstanding, the
     shares of Preferred Stock issuable upon exercise of this Warrant and the
     Common Stock issuable upon conversion of such shares of Preferred Stock
     shall be entitled to all rights and benefits accorded thereto in any
     investor rights or shareholders or similar agreement between and/or among
     the Corporation and the holders of the Preferred Stock, and the Corporation
     shall take all actions and shall execute and deliver all documents
     necessary or desirable, including any amendments to such agreement(s) to
     make the holder a party thereto.

          (b)  Anything contained herein to the contrary notwithstanding, the
     holder of this Warrant shall be entitled to the rights set forth on
     Exhibit A hereto.
     ---------

10.  Transfer of Warrant; Amendment.
     ------------------------------

     Subject to the restriction set forth in Section 7, this Warrant and all
rights hereunder are transferable, in whole, or in part, at the agency or office
of the Corporation referred to in Section 2, by the holder hereof in person or
by duly authorized attorney, upon surrender of this Warrant properly endorsed;
provided, however, that prior to the IPO, transfers by any holder of this
--------  -------
Warrant to a person or entity other than an affiliate of such holder shall
require the prior written consent of the Corporation.  Each taker and holder of
this Warrant, by taking or holding the same, consents and agrees that this
Warrant, when endorsed, in blank, shall be deemed negotiable, and, when so
endorsed the holder hereof may be treated by the Corporation and all other
persons dealing with this Warrant as the absolute owner hereof for any purposes
and as the person entitled to exercise the rights represented by this Warrant,
or to the transfer hereof on the books of the Corporation, any notice to the
contrary notwithstanding; but until each transfer on such books, the Corporation
may treat the registered holder hereof as the owner hereof for all purposes.

11.  Reorganizations, Etc.  In case, at any time during the Exercise Period, of
     --------------------
any capital reorganization, of any reclassification of the stock of the
Corporation (other than a change in par value or from par value to no par value
or from no par value to par value or as a result of a stock dividend or
subdivision, split-up or combination of shares), or the consolidation or merger
of the Corporation with or into another corporation (other than a consolidation
or merger in which the Corporation is the continuing operation and which does
not result in any change in the Common Stock) or of the sale of all or
substantially all the properties and assets of the Corporation as an entirety to
any other corporation, this Warrant shall, after such reorganization,
reclassification, consolidation, merger or sale, be exercisable for the kind and
number of shares of stock or other

                                       8
<PAGE>

securities or property of the Corporation or of the corporation resulting from
such consolidation or surviving such merger or to which such properties and
assets shall have been sold to which such holder would have been entitled if he
had held the Preferred Stock issuable upon the exercise of this Warrant or the
Common Stock issuable upon conversion of the Preferred Stock immediately prior
to such reorganization, reclassification, consolidation, merger or sale. In any
such reorganization or other action or transaction described above, 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 Warrant 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, in relation to any shares of
stock, securities or assets thereafter deliverable upon the exercise hereof.

12.  Lost, Stolen, Mutilated or Destroyed Warrant.  If this Warrant is lost,
     --------------------------------------------
stolen, mutilated or destroyed, the Corporation may, on such terms as to
indemnity or otherwise as it may in its discretion impose (which shall, in the
case of a mutilated Warrant, include the surrender thereof), issue a new Warrant
of like denomination and tenor as the Warrant so lost, stolen, mutilated or
destroyed.  Any such new Warrant shall constitute an original contractual
obligation of the Corporation, whether or not the allegedly lost, stolen,
mutilated or destroyed Warrant shall be at any time enforceable by anyone.

13.  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.

14.  Notices.  All notices, advices and communications to be given or otherwise
     -------
made to any party to this Agreement shall be deemed to be sufficient if
contained in a written instrument delivered in person or by telecopier or duly
sent by first class registered or certified mail, return receipt requested,
postage prepaid, or by overnight courier, or by electronic mail, with a copy
thereof to be sent by mail (as aforesaid) within 24 hours of such electronic
mail, addressed to such party at the address set forth below or at such other
address as may hereafter be designated in writing by the addressee to the
addresser listing all parties:

          (a)  If to the Corporation, to:

               DigitalWork.com, Inc.
               230 West Monroe Street, Suite 1950
               Chicago, Illinois  60606
               Attention:  Craig Terrill, President
               Telecopier:
               e-mail address:
                                      and

          (b)  If to AOL as follows:

                                       9
<PAGE>

               America Online, Inc.
               22000 AOL Way
               Dulles, Virginia 20166
               Attention:  General Counsel
               Telecopier:  (703) 265-2208
               e-mail address:

Or to such other address as the party to whom notice is to be given may have
furnished to the other parties hereto in writing in accordance herewith.  Any
such notice or communication shall be deemed to have been delivered and received
(i) in the case of personal delivery or delivery by telecopier, on the date of
such deliver, (ii) in the case of nationally-recognized overnight courier, on
the next business day after the date when sent and (ii) in the case of mailing,
on the third business day following that on which the piece of mail containing
such communication is posted.  As used in this Section 13, "business day" shall
mean any day other than a day on which banking institutions in the Commonwealth
of Virginia are legally closed for business.

15.  Binding Effect on Successors; Survival.  This Warrant shall be binding upon
     --------------------------------------
any corporation succeeding the Corporation by merger, consolidation or
acquisition of all or substantially all of the Corporation's assets.  All of the
obligations of the Corporation relating to the Preferred Stock issuable upon the
exercise of this Warrant or the Common Stock issuable upon conversion of the
Preferred Stock shall survive the exercise and termination of this Warrant.  All
of the covenants and agreements of the Corporation shall inure to the benefit of
the successors and assigns of AOL.

16.  Descriptive Headings and Governing Law.  The description 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 Commonwealth of Virginia.

17.  Fractional Shares.  No fractional shares shall be issued upon exercise of
     -----------------
this Warrant.  The Corporation 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 Fair Market Value of one Warrant Share.

                                     * * *

                                       10
<PAGE>

          IN WITNESS WHEREOF, the undersigned have caused this Warrant and
Warrant Agreement to be executed by their duly authorized officers on the date
first above written.

                                           DIGITALWORK.COM, INC.

                                           By:  /s/ John Banta
                                           Name:    John Banta
                                           Title:   Vice President

                                       11
<PAGE>

                              Form of Subscription

                    [To be signed upon exercise of Warrant]

          The undersigned, the holder of the Warrant, hereby irrevocably elects
to exercise the purchase rights represented by such Warrant for, and to purchase
thereunder, _________ shares of _________ of DigitalWork.com, Inc. and herewith
makes payment of $_________ therefor, and requests that the certificates for
such shares be issued in the name of and delivered to, ______________________,
whose address is _________________________.

Dated:_____________
                              _________________________________
                              (Signature)

                              _________________________________
                              (Address)

                                       12
<PAGE>

                               Notice of Exchange

                       (To be executed by the Holder in
                        order to exchange the Warrant.)

          The undersigned hereby irrevocably elects to exchange this Warrant
into __________ shares (the foregoing number constituting the number of Warrant
Shares to be issued pursuant to Section 3 of this Warrant) of ________ of
DigitalWork.com, Inc., minus any shares to be deducted from the foregoing number
in accordance with the terms of this Warrant, according to the conditions
thereof.  The undersigned desires to consummate such exchange on
________________.

Dated:

                              _____________________________
                              Name of Holder:

                              By:__________________________

                                       13
<PAGE>

                               Form of Assignment

                  [To be signed only upon transfer of Warrant]

          For value received, the undersigned hereby sells, assigns and
transfers unto the right represented by the Warrant to purchase _______ shares
of _________ of DigitalWork.com, Inc., to which the Warrant relates, and
appoints Attorney to transfer such right on the books of [ISSUER], with full
power of substitution in the premises.

Dated:_____________

                              ____________________________
                              (Signature)

Signed in the presence of:

______________________________

                                       14
<PAGE>

                                   EXHIBIT A
                                   ---------

          Reference is made to the Series D Convertible Preferred Stock Purchase
Agreement dated as of December 2, 1999 (the "Series D Purchase Agreement"),
DigitalWork.com, Inc. and the Purchasers (as defined therein).  Capitalized
terms used in this Exhibit A and not defined herein shall have the respective
                   ---------
meanings assigned to them in the Series D Purchase Agreement.

          The Company hereby covenants and agrees to grant to AOL, and does
hereby grant to AOL on and as of the date hereof, the rights set forth in
Sections 6.01, 6.02 and 6.07 of the Series D Purchase Agreement as if AOL were a
Purchaser thereunder, and such sections of the Series D Purchase Agreement are
incorporated herein by reference; provided, that for purposes of calculating
                                  --------
AOL's percentage of equity ownership of the Corporation in Section 6.02 of the
Series D Purchase Agreement, AOL shall be deemed to be a holder of the number of
shares of Series D Preferred and/or Common Stock for which this Warrant is
exercisable.

                                       15

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