Document:

<PAGE>

                                                                   EXHIBIT 10.23

                   MANAGEMENT BONUS STOCK PURCHASE AGREEMENT
                   -----------------------------------------

          This MANAGEMENT BONUS STOCK PURCHASE AGREEMENT (this "Agreement") is
made as of December 20, 1999 by and among the individual signatory hereto (the

"Purchaser") IWO Holdings, Inc., a Delaware corporation ("Holdings") and IWO
----------                                                --------
Holdings Limited, a Cayman Islands company ("Seller").
                                             ------

                                R E C I T A L S
                                ---------------

     WHEREAS, the Purchaser is an employee of Holdings and Independent Wireless
One Corporation (the "Company"), a Subsidiary of Holdings, and desires to
                      -------
increase his equity interest in Holdings;

     WHEREAS, subject to the terms and conditions hereof, Seller is willing to
sell to the Purchaser the number of shares of Class B Common Stock, par value
$.01 per share ("Class B Common Stock"), of Holdings as determined by the
calculation set forth on Schedule 1 hereto (the "Shares") at a price per share
                         ----------
set forth on Schedule 1 hereto ("Cost");
             ----------          ----

     WHEREAS, the Buyer desires to purchase the Shares, subject to terms and
conditions and the rights of the Seller and Holdings and the other parties
hereto as set forth herein; and

     WHEREAS, in consideration of the actions described above and contemplated
herein, the parties hereto desire to set forth herein certain agreements
regarding their rights and obligations with respect to the Shares.

                                   AGREEMENT
                                   ---------

     NOW, THEREFORE, in consideration of the mutual covenants, agreements,
representations and warranties and subject to the conditions contained herein,
the Purchaser and Holdings hereby agree as follows:

          1.  Definitions.  Capitalized terms used herein shall have the
              -----------
following meanings:

          "Act" means the Securities Exchange Act of 1933, as amended.
           ---

          "Affiliate" means (a) any Person which, directly or indirectly, is in
           ---------
control of, is controlled by, or is under common control with, such Person or
(b) any Person who is a director or officer (i) of such Person, (ii) of any
subsidiary of such Person or (iii) of any Person described in clause (a) above.
For purposes of this definition, "control" of a Person means the power, directly
or indirectly, (x) to vote 50% or more of the securities having ordinary voting
power for the election of directors of such Person whether by
<PAGE>

ownership of securities, contract, proxy or otherwise, or (y) to direct or cause
the direction of the management and policies of such Person whether by ownership
of securities, contract, proxy or otherwise.

          "Agreement" has the meaning specified in the preamble.
           ---------

          "Approved Sale" means a transaction or a series of related
           -------------
transactions which results in a change of economic beneficial ownership of
Holdings or its business of greater than 50% (disregarding for this purpose any
disparate voting rights attributable to the outstanding stock of Holdings),
whether pursuant to the sale of the stock of Holdings, the sale of all or
substantially all of the assets of Holdings, or a merger or consolidation;
provided that a sale of stock by an Initial Stockholder to (i) another Initial
Stockholder or Affiliate thereof, or (ii) a non-U.S. entity with respect to
which an Initial Stockholder or Affiliate thereof has an administrative
relationship shall be disregarded when determining if an Approved Sale has
occurred.

          "Bonus" means the bonus paid to Purchaser on the Closing Date for the
           -----
calendar year 1999 as provided in the Employment Agreement.

          "Cause" has the meaning set forth in the Employment Agreement.
           -----

          "Certificate of Incorporation" means the Amended and Restated
           ----------------------------
Certificate of Incorporation of Holdings, as amended from time to time.

          "Class B Common Stock" has the meaning specified in the Recitals.
           --------------------

          "Closing Date" means December 20, 1999.
           ------------

          "Company" has the meaning specified in the Recitals.
           -------

          "Consolidation Transaction" means a transaction or series of related
           -------------------------
transactions (including mergers, reorganizations, liquidations, share exchanges
and/or consolidations involving Holdings and one or more of its direct and
indirect wholly-owned subsidiaries) effected to implement a reorganization of
Holdings (and one or more of such subsidiaries) (or similar transactions) that
does not result in a material change in beneficial ownership of the voting
securities of Holdings or its successor.

          "Cost" has the meaning specified in the Recitals.
           ----

          "Disability" has the meaning specified in the Employment Agreement.
           ----------

          "Employment Agreement" means the Employment Agreement between the
           --------------------
Purchaser and the Company, dated as of the date set forth on the signature page
hereof, as may be amended from time to time.

          "Endorsed Certificate" has the meaning specified in Section 3(a).
           --------------------

                                       2
<PAGE>

          "Fair Market Value" means the value of a Share, as of the Termination
           -----------------
Date, determined pursuant to Section 4(c).

          "Holdings" has the meaning specified in the preamble.
           --------

          "Initial Public Offering" means the sale of any of the common stock of
           -----------------------
Holdings pursuant to a registration statement that has been declared effective
under the Act, if as a result of such sale (i) the issuer becomes a reporting
company under Section 12(b) or 12(g) of the Securities Exchange Act of 1934, as
amended, and (ii) such stock is traded on the New York Stock Exchange or the
American Stock Exchange, or is quoted on the Nasdaq National Market, or is
traded or quoted on any other national stock exchange or national securities
system.

          "Initial Stockholders" means the stockholders of Holdings who became
           --------------------
stockholders as of the date hereof (including employees or directors of Holdings
or any Subsidiary who were granted options to purchase stock as of the date
hereof ) and any transferees of such stockholders described in clause (i) or
(ii) in the definition of Approved Sale.

          "Permitted Transferee" means a Purchaser's spouse, child, estate,
           --------------------
personal representative, heir or successor, or a trust for the benefit of such
Purchaser or such Purchaser's spouse, child or heir or to a partnership or
limited liability company the partners or members of which consist solely of
such Purchaser or such Purchaser's spouse, children or heirs.

          "Person" means an individual, partnership, joint venture, limited
           ------
liability company, corporation, trust, unincorporated organization or a
government or any department or agency thereof.

          "Post-Tax Bonus" means an amount equal to 50% of the Bonus.
           --------------

          "Purchaser" has the meaning specified in the preamble.
           ---------

          "Put Period" and "Put Right" have the meanings specified in Section
           ----------       ---------
3(b).

          "Repurchase Period" and "Repurchase Right" have the meanings specified
           -----------------       ----------------
in Section 3(a).

          "Retirement" means obtaining age 65.
           ----------

          "Shares" has the meaning specified in the Recitals.
           ------

          "Subsidiary" means any joint venture, corporation, partnership or
           ----------
other entity as to which Holdings, whether directly or indirectly, has more than
50% of the (i) voting rights or (ii) rights to capital or profits.

          "Termination Date" means the date on which the Purchaser ceases to be
           ----------------
employed by the Company for any reason.

                                       3
<PAGE>

          2.  Subscription for and Purchase of Shares.
              ---------------------------------------

              (a) The Seller agrees to sell and deliver to the Purchaser, and
the Purchaser agrees to buy from the Seller, within five days of receipt by
Purchaser of the Bonus (the "Purchase Date"), the Shares at a price per Share
                             -------------
equal to Cost for the aggregate purchase price equal to 33 1/3% of the Post-Tax
Bonus (the "Purchase Price"). On the Purchase Date, the Seller shall withhold
            --------------
from the Purchaser's bonus or Purchaser shall pay to the Seller by personal
check an amount equal to the Purchase Price. As soon as practicable after
receipt of such payment (but in any event not before collection with respect to
any personal check), the Seller shall deliver to the Purchaser one or more
certificates evidencing the Shares in proper form for transfer by delivery or
with duly executed transfer powers attached thereto.

          (b) The obligations of Seller and the Purchaser set forth in this
Agreement are contingent upon the receipt by the Purchaser of a Bonus.

          3.  Repurchase of Shares.
              --------------------

              (a) If the Purchaser's employment by the Company is terminated
prior to the earlier of an Initial Public Offering or Approved Sale for any
reason, Holdings, during the sixty (60) days following the Termination Date
(subject to Section 3(e)), the "Repurchase Period"), shall have the right to
                                -----------------
purchase all, but not less than all, of the Shares which have been beneficially
owned by the Purchaser (the "Repurchase Right"). The purchase price for each
                             ----------------
Share shall be determined in accordance with Exhibit 2 hereto. If Holdings
elects to purchase the Shares, it shall notify the Purchaser at or before the
end of the Repurchase Period of such election and the purchase price shall be
paid in cash at a time set by Holdings within 30 days after the end of the
Repurchase Period, provided that the Purchaser has presented to Holdings a stock
certificate evidencing the Shares duly endorsed for transfer (the "Endorsed
                                                                   --------
Certificate"). If the Purchaser fails to deliver the Endorsed Certificate, the
-----------
Shares represented thereby shall be deemed to have been purchased upon (i) the
payment by Holdings of the purchase price to the Purchaser or the Purchaser's
Permitted Transferee or (ii) notice to the Purchaser or such Permitted
Transferee that Holdings is holding the purchase price for the account of the
Purchaser or such Permitted Transferee, and upon such payment or notice the
Purchaser and such Permitted Transferee will have no further rights in or to
such Shares. Holdings may assign its rights to the Stockholders under the
Stockholders Agreement in the manner contemplated by Section __ thereof. If the
Shares are not purchased pursuant to Section 3(a) or 3(b), the restrictions on
transfer thereof contained in this Agreement shall terminate and be of no
further force and effect. Upon the earlier of an Initial Public Offering or
Approved Sale, the rights contained in Sections 3(a) and 3(b) of this Agreement
shall terminate and be of no further force and effect.

          (b) If the Purchaser's employment by the Company is terminated prior
to the earlier of an Initial Public Offering or an Approved Sale (i) by the
Company without Cause; (ii) due to the Purchaser's Retirement, death or
Disability or departure ; (iii) by the Purchaser for any reason after December
31, 2001 or prior to such date due to personal hardship as determined by the
Board of  Directors of Holdings or

                                       4
<PAGE>

(iv) by the Company with Cause after December 31, 2002, the Purchaser or the
Purchaser's representative, during the 120 days following the Termination Date
(subject to Section 3(e), the "Put Period"), shall have the right (the "Put
                               ----------                               ---
Right") to require Holdings to purchase all, but not less than all, of the
-----
Shares then owned by the Purchaser. The purchase price for each Share shall be
the amount set forth on Exhibit 2. The purchase price shall be paid in cash at a
time set by Holdings, within 30 days after the end of the Put Period, provided
that Holdings need not pay the purchase price until such later time that the
Purchaser presents to Holdings the Endorsed Certificate. Holdings may delegate
its duties under this Section 4(b) to an Affiliate of Holdings provided such
Affiliate accepts such delegation in writing.

          (c) The Fair Market Value of the Shares to be purchased by Holdings
hereunder shall be determined in good faith by the Holding's Board of Directors.
The Board of Directors shall make its determination of Fair Market Value
annually (the "Annual Valuation") promptly after the completion of Holding's
               ----------------
audited financial statements for the year then completed and such determination
shall remain in effect until the Board of Directors makes the next Annual
Valuation.  Notwithstanding the foregoing, if the Board of Directors or an
investment banker or appraiser appointed by Holdings makes a determination of
Fair Market Value subsequent to an Annual Valuation, such subsequent
determination shall supersede the Annual Valuation then in effect and shall
establish the Fair Market Value until the next Annual Valuation.  The Fair
Market Value shall be based on an assumed sale of 100% of the outstanding
capital stock of Holdings (without reduction for minority interest or lack of
liquidity of the Shares or similar discount).  If such determination of the Fair
Market Value is challenged by the Purchaser, the Board of Directors will select
an appraiser or investment banker with a national reputation who is independent
(not an Affiliate of the parties) (the "Appraiser") and who shall establish the
Fair Market Value as of the date of valuation referenced in the Annual Valuation
or a subsequent determination.  The Appraiser's determination shall be
conclusive and binding on Holdings and Purchaser.  Holdings shall bear all costs
incurred in connection with the services of such Appraiser.

          (d) The Purchaser shall not be considered to have ceased to be
employed by the Company for purposes of this Agreement if he continues to be
employed by the Company or a Subsidiary, or by a company of which the Company is
a Subsidiary.

          4.  Representations and Warranties of Holdings.  Holdings hereby
              ------------------------------------------
represents and warrants to the Purchaser as follows:

               (a) Holdings is a corporation duly organized, validly existing
     and in good standing under the laws of the State of Delaware.

               (b) Holdings has full corporate power and authority to enter into
     and consummate the transactions contemplated by this Agreement.  This
     Agreement constitutes a legal, valid and binding obligation of Holdings and
     has been authorized by all necessary corporate action.

                                       5
<PAGE>

          5.  Representations and Warranties of the Purchaser.  The Purchaser
              -----------------------------------------------
hereby represents and warrants that:

              (a) The Purchaser is acquiring the Shares for investment for the
Purchaser's own account and without view to further distribution of the Shares.

              (b) The Purchaser is an employee of the Company and has been given
access to all information that the Purchaser considers necessary to make an
investment decision as to the Shares.

          6.  Acknowledgments and Agreements of the Purchaser.  The Purchaser
              -----------------------------------------------
acknowledges and agrees that:

              (a) The Shares have not been registered under the Act or under the
securities laws of any state and must be held by the Purchaser for at least one
year unless the Shares are subsequently registered under the Act and any
applicable state securities laws; or an exemption from registration under the
Act becomes or is available.

              (b) The Shares are subject to the terms and conditions of the
Certificate of Incorporation.  Under certain conditions as specified in the
Certificate of Incorporation, the Shares could be subject to mandatory
redemption by Holdings.

              (c) The Shares are subject to the terms and provisions of the
Stockholders Agreement (the "Stockholders Agreement") by and between Holdings
and the Stockholders, as such term is defined in the Stockholders Agreement, and
the Purchaser shall be treated as a Class B Stockholder under the Stockholders
Agreement with respect to the Shares.

          7.  Representations of the Seller.  The Seller represents and warrants
              -----------------------------
that:

              (a) The Seller is a company duly organized, validly existing and
in good standing under the laws of the Cayman Islands.

              (b) The Seller has full corporate power and authority to enter
into and consummate the transactions contemplated by this Agreement. This
Agreement constitutes a legal, valid and binding obligation of the Seller,
except as the same may be limited by applicable bankruptcy, insolvency,
reorganization, moratorium or similar laws of general application relating to or
affecting creditors' rights, and for the limitations imposed by general
principles of equity, and has been authorized and approved by all necessary
corporate action.

              (c) The Seller is the lawful owner of the Shares and has valid and
marketable title to the Shares, and upon delivery of and payment for the Shares,
the Purchaser will acquire valid and marketable title to the Shares free and
clear of any liens or encumbrances other than those created by the Certificate
of Incorporation or the

                                       6
<PAGE>

Stockholders Agreement, dated as of the date hereof, by and among Holdings and
certain stockholders of Holdings.

          8.  Notices.  Any notice or other document required or permitted to be
              -------
given or delivered to the Purchaser pursuant to the terms of this Agreement
shall be delivered at, or sent by certified or registered mail to the Purchaser
at the address for such Purchaser set forth on the signature page hereto or to
such other address as shall have been furnished to Holdings and to the Seller in
writing by the Purchaser.

          Any notice or other document required or permitted to be given or
delivered to Holdings shall be sent by certified or registered mail to Holdings
at:

          IWO Holdings, Inc.
          c/o Gibson, Dunn & Crutcher LLP
          200 Park Avenue, 47th Floor
          New York, NY  10166-0193
          Attention:  Sean P. Griffiths

with a copy to

          Gibson, Dunn & Crutcher LLP
          200 Park Avenue, 47th Floor
          New York, NY  10166
          Attention:  Sean P. Griffiths

or to such other address as shall have been furnished to the Purchaser and
Seller in writing by Holdings.

          Any notice or other document required or permitted to be given or
delivered to the Seller shall be sent by certified or registered mail to the
Seller at:

          IWO Holdings Limited
          c/o Gibson, Dunn & Crutcher LLP
          200 Park Avenue, 47th Floor
          New York, NY  10166-0193
          Attention:  Sean P. Griffiths

with a copy to

          Gibson, Dunn & Crutcher LLP
          200 Park Avenue, 47th Floor
          New York, NY  10166
          Attention:  Sean P. Griffiths

or to such other address as shall have been furnished in writing to the
Purchaser and Holdings.

                                       7
<PAGE>

          9.  Severability.  Whenever possible, each provision of this Agreement
              ------------
shall be interpreted in such manner as to be effective and valid under
applicable law, but if any provision of this Agreement is held to be prohibited
by or invalid under applicable law, such provision shall be ineffective only to
the extent of such prohibition or invalidity, without invalidating the remainder
of this Agreement.

          10.  Counterparts.  This Agreement may be executed in two
               ------------
counterparts, each of which shall be deemed an original as against the party who
has signed it, but both of which together shall constitute one and the same
Agreement.

          11.  Assignment.  This Agreement and all the provisions hereof shall
               ----------
be binding and shall inure to the benefit of the parties hereto and their
respective successors and permitted assigns, whether expressed or not, but
neither this Agreement nor any of the rights, interests, duties or obligations
hereunder may be assigned by either party hereto without the prior written
consent of the other party.  In the event that the Shares are at any time
transferred to any person, the transferee shall take such Shares subject to and
pursuant to all the terms, provisions, conditions and covenants of this
Agreement.

          12.  Miscellaneous.  (a) This Agreement and the rights and obligations
               -------------
of the parties hereunder shall be governed by and construed in accordance with
the internal laws of the State of New York without regard to principles of
choice of laws or conflicts of laws thereof, (b) this Agreement and any
provisions hereof may be changed, waived, discharged or terminated only by an
instrument in writing signed by the party against which an enforcement of the
same is sought, (c) the descriptive headings of this Agreement are for
convenience only and do not constitute a part of this Agreement.

                                       8
<PAGE>

          IN WITNESS WHEREOF, the parties hereto have executed this Agreement as
of the day and year first above written.

                                    IWO HOLDINGS LIMITED

                                    By:_________________________
                                       Name:
                                       Title:

                                    IWO HOLDINGS, INC.

                                    By:_____________________
                                       Name:
                                       Title:

                                    "Purchaser"

                                    By:_________________________
                                       Name:
                                       Address:

                                       Date of Employment Agreement:<PAGE>

                                                                   EXHIBIT 10.24

THIS WARRANT AND THE SHARES OF CLASS B COMMON STOCK PURCHASABLE HEREUNDER HAVE
NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR UNDER THE
SECURITIES LAWS OF ANY STATE OR OTHER JURISDICTION AND MAY NOT BE SOLD, OFFERED
FOR SALE OR OTHERWISE TRANSFERRED UNLESS REGISTERED OR QUALIFIED UNDER SAID ACT
AND APPLICABLE STATE SECURITIES LAWS OR UNLESS AN EXEMPTION IS AVAILABLE AND AN
OPINION OF COUNSEL REASONABLY ACCEPTABLE TO THE CORPORATION IS DELIVERED TO SUCH
EFFECT.

THESE SECURITIES ARE SUBJECT TO MANDATORY REDEMPTION BY THE CORPORATION.  SUCH
REDEMPTION CAN BE ACCOMPLISHED WITHOUT THE CERTIFICATES REPRESENTING SUCH
SECURITIES BEING SURRENDERED AND WHETHER OR NOT THE CORPORATION GIVES NOTICE OF
SUCH REDEMPTION.  THE CORPORATION WILL FURNISH WITHOUT CHARGE TO EACH HOLDER WHO
SO REQUESTS THE POWERS, DESIGNATIONS, PREFERENCES AND RELATIVE, PARTICIPATING,
OPTIONAL OR OTHER SPECIAL RIGHTS OF EACH CLASS OF STOCK OR SERIES THEREOF AND
THE QUALIFICATIONS, LIMITATIONS OR RESTRICTIONS OF SUCH PREFERENCES AND/OR
RIGHTS.

AS SPECIFIED HEREIN AND IN THE AMENDED AND RESTATED CERTIFICATE OF INCORPORATION
OF THE CORPORATION AND THE STOCKHOLDERS AGREEMENT, DATED AS OF DECEMBER 20,
1999, BY AND AMONG THE CORPORATION AND CERTAIN STOCKHOLDERS OF THE CORPORATION,
THE TRANSFERABILITY OF THESE SECURITIES IS SUBJECT TO RESTRICTION.

      Void after 5:00 p.m., New York, New York Time, on December 20, 2009.
    (Subject to earlier termination upon an Approved Sale or Termination of
                                  Employment)

                              WARRANT TO PURCHASE
                                   SHARES OF
                              CLASS B COMMON STOCK

                                       OF

                               IWO HOLDINGS, INC.

     This is to certify that, FOR VALUE RECEIVED, __________, residing at
_____________________ ("Holder"), is entitled to purchase, subject to the
                        ------
provisions of this Warrant, from IWO Holdings, Inc., a Delaware corporation

("Holdings"), up to 2,480 fully paid, validly issued and nonassessable shares of
----------
Class B Common Stock, $0.01 par value per share (the "Class B Common Stock"), at
                                                      --------------------
the exercise price of $172.34043 per share until December 20, 2009, subject to
earlier termination upon an Approved Sale or in the event of the termination of
Holder's employment with Holdings or any of its Subsidiaries.  The number of
shares of Class B Common Stock to be received upon the exercise of this Warrant
and the price to be paid for each
<PAGE>

share of Class B Common Stock are subject to adjustment as hereinafter set
forth. The shares of Class B Common Stock deliverable upon such exercise, and as
adjusted from time to time, are hereinafter sometimes referred to as "Warrant
                                                                      -------
Shares," and the exercise price for a share of Class B Common Stock, as adjusted
------
from time to time is hereinafter sometimes referred to as the "Exercise Price."
                                                               --------------

     1.  CERTAIN DEFINITIONS.  As used herein, the following terms shall have
         -------------------
the following meanings:

     "40% IRR Warrant" means Warrants with respect to 1,240 shares of Class B
      ---------------
Common Stock.

     "60% IRR Warrant" means Warrants with respect to 1,240 shares of Class B
      ---------------
Common Stock.

     "Affiliate" means (a) any Person which, directly or indirectly, is in
      ---------
control of, is controlled by, or is under common control with, such Person or
(b) any Person who is a director or officer (i) of such Person, (ii) of any
Subsidiary of such Person or (iii) of any Person described in clause (a) above.
For purposes of this definition, "control" of a Person means the power, directly
or indirectly, (x) to vote 50% or more of the securities having ordinary voting
power for the election of directors of such Person whether by ownership of
securities, contract, proxy or otherwise, or (y) to direct or cause the
direction of the management and policies of such Person whether by ownership of
securities, contract, proxy or otherwise.

     "Approved Sale" means a transaction or a series of related transactions
      -------------
which results in a change of economic beneficial ownership of Holdings or its
business of greater than 50% (disregarding for this purpose any disparate voting
rights attributable to the outstanding stock of Holdings), whether pursuant to
the sale of the stock of Holdings, the sale of all or substantially all of the
assets of Holdings, or a merger or consolidation; provided that a sale of stock
by an Initial Stockholder to (i) another Initial Stockholder or Affiliate
thereof, or (ii) a non-U.S. entity with respect to which an Initial Stockholder
or Affiliate thereof has an administrative relationship shall be disregarded
when determining if an Approved Sale has occurred.

     "Cause" has the meaning provided in the Employment Agreement dated as of
      -----
the date hereof between the Holder and Holdings.

     "Certificate of Incorporation" means the Amended and Restated Certificate
      ----------------------------
of Incorporation of Holdings, dated December 16, 1999, as amended from time to
time.

     "Class A Common Stock" means the Class A common stock of Holdings, $0.01
      --------------------
par value per share.

     "Class B Common Stock" is defined in the preamble.
      --------------------

     "Class D Common Stock" means the Class D common stock of Holdings, $0.01
      --------------------
par value per share.

     "Common Stock" means the common stock of Holdings, $0.01 par value per
      ------------
share.

                                       2
<PAGE>

     "Dilution Event" is defined in Section 7(a).
      --------------

     "Disability" has the meaning provided in the Employment Agreement dated as
      ----------
of the date hereof between the Holder and Holdings.

     "Exercise Price" is defined in the Preamble.
      --------------

     "Holder" is defined in the Preamble.
      ------

     "Holdings" is defined in the preamble.
      --------

     "Holdings Notice" is defined in Section 2(b).
      ---------------

     "Initial Investors" means the owners of the Class A Common Stock, Class C
      -----------------
Common Stock and Class D Common Stock as of the date hereof, other than Paribas
North America, Inc.

     "Initial Investors Cash-Out" is defined in Section 2(a).
      --------------------------

     "Initial Investors Investment" means the investment in Holdings that the
      ----------------------------
Initial Investors have made on the date hereof.

     "Initial Public Offering" means the effectiveness after December 31, 1999
      -----------------------
of a registration statement under the Securities Act on any of Forms S-1, S-2,
S-3 or any similar successor form covering any of the Stock, and the completion
of a sale of such Stock thereunder, (i) following which Holdings is, or becomes,
a reporting company under Section 12(b) or 12(g) of the Exchange Act, and (ii)
as a result of which the Common Stock is traded on the New York Stock Exchange
or the American Stock Exchange, or quoted on the Nasdaq Stock Market or is
traded or quoted on any other national stock exchange.

     "Initial Stockholders" means the stockholders of Holdings who became
      --------------------
stockholders as of the Closing Date (including employees or directors of
Holdings or any Subsidiary who were granted options to purchase stock as of the
Closing Date) and any transferees of such stockholders described in clause (i)
or (ii) in the definition of Approved Sale.

     "Notice Date" is defined in Section 2(c).
      -----------

     "Notice of Exercise" is defined in Section 2(c).
      ------------------

     "Permitted Transferee" is defined in Section 5.
      --------------------

     "Person" means an individual, partnership, joint venture, limited liability
      ------
company, corporation, trust, unincorporated organization or a government or any
department or agency thereof.

     "Retirement" has the meaning provided in the Employment Agreement dated as
      ----------
of the date hereof between the Holder and Holdings.

     "Securities Act" means the Securities Act of 1933, as amended, and the
      --------------
rules and regulations promulgated thereunder.

                                       3
<PAGE>

     "Subsidiary" means any joint venture, corporation, partnership or other
      ----------
entity as to which Holdings, whether directly or indirectly, has more than 50%
of the (i) voting rights or (ii) rights to capital or profits.

     "Supermajority Board Approval" means the affirmative vote of a majority of
      ----------------------------
the authorized number of directors including the affirmative vote of any two
directors who are Founders Designated Directors, the Odyssey Designated Director
or the Chief Executive Officer.

     "Termination of Employment" means the date on which the Holder ceases to be
      -------------------------
employed by Holdings or any of its Subsidiaries for any reason.

     "Warrant" means the rights granted by Holdings to the Holder pursuant
      -------
hereto to purchase Warrant Shares.

     "Warrant Shares" means the shares of Class B Common Stock purchased or
      --------------
purchasable by the Holder pursuant to the terms of this Warrant.

     2.  VESTING AND EXERCISE OF WARRANT.
         -------------------------------

     (a) The 40% IRR Warrant shall vest and become exercisable in full upon the
earliest to occur of the following, provided such occurrence is prior to the
Termination of Employment:

         (i)    immediately prior to the closing of an Approved Sale pursuant to
     which the Initial Investors realize on the shares of Class A Common Stock,
     Class C Common Stock and Class D Common Stock (or Common Stock issued upon
     conversion thereof) sold by the Initial Investors in such Approved Sale an
     amount in cash greater than the product of 2 multiplied by the Initial
     Investors Investment and such amount represents a forty percent (40%)
     annual return on the Initial Investors Investment, compounded from the date
     hereof to the closing date of such Approved Sale;

         (ii)   immediately prior to the closing of an Approved Sale that (A) is
     prior to the closing of the Initial Public Offering and (B) is approved by
     less than a Supermajority Vote of the Board and such approval occurs on a
     date prior to the first anniversary of the date hereof; or

         (iii)  if an Initial Public Offering has occurred, 90 days following
     the closing of a transaction or the last of a series of transactions that
     results in the Initial Investors having disposed of 50% of the shares of
     Class A Common Stock, Class C Common Stock and Class D Common Stock owned
     by them as of the date hereof (or Common Stock issued upon conversion
     thereof) (an "Initial Investors Cash-Out") and as a result of such
                   --------------------------
     transaction or the last of such series of transactions, the Initial
     Investors have realized in cash an amount greater than the product of 1.5
     multiplied by the Initial Investors Investment and such amount, together
     with the amount the Initial Investors could realize in the public sale of
     the remaining shares owned by the Initial Investors as of the date hereof,
     represents a forty percent (40%) annual return on the Initial Investors
     Investment, compounded from the date hereof to the date 90 days following
     the date of the

                                       4
<PAGE>

     Initial Investors Cash-Out. The amount that could be realized by the
     Initial Investors in the public sale of such remaining shares shall be
     deemed to be an amount per share equal to the average closing sale price of
     the Common Stock as traded on the New York Stock Exchange or American Stock
     Exchange or as reported on the Nasdaq National Market over the 90-day
     period following the date of the Initial Investors Cash-Out.

     (b) The 60% IRR Warrant shall vest and become exercisable in full upon the
earlier to occur of the following, provided such occurrence is prior to the
Termination of Employment:

         (i)    immediately prior to the closing of an Approved Sale pursuant to
     which the Initial Investors realize on the shares of Class A Common Stock,
     Class C Common Stock and Class D Common Stock (or Common Stock issued upon
     conversion thereof) sold by the Initial Investors in such Approved Sale an
     amount in cash greater than the product of 3 multiplied by the Initial
     Investors Investment and such amount represents a sixty percent (60%)
     annual return on the Initial Investors Investment, compounded from the date
     hereof to the closing date of such Approved Sale;

         (ii)   immediately prior to the closing of an Approved Sale that (A) is
     prior to the closing of the Initial Public Offering and (B) is approved by
     less than a Supermajority Vote of the Board and such approval occurs on a
     date prior to the first anniversary of the date hereof; or

         (iii)  if an Initial Public Offering has occurred, 90 days following an
     Initial Investors Cash-Out and as a result of such transaction or the last
     of such series of transactions, the Initial Investors have realized in cash
     an amount greater than the product of 3 multiplied by the Initial Investors
     Investment and such amount, together with the amount the Initial Investors
     could realize in the public sale of the remaining shares owned by the
     Initial Investors as of the date hereof, represents a sixty percent (60%)
     annual return on the Initial Investors Investment, compounded from the date
     hereof to the date 90 days following the date of the Initial Investors
     Cash-Out.  The amount that could be realized by the Initial Investors in
     the public sale of such remaining shares shall be deemed to be an amount
     per share equal to the average closing sale price of the Common Stock as
     traded on the New York Stock Exchange or American Stock Exchange or as
     reported on the Nasdaq National Market over the 90-day period following the
     date of the Initial Investors Cash-Out.

     (c) Holdings shall give to the Holder written notice (the "Holdings
                                                                --------
Notice") of the occurrence of an Approved Sale at least 20 days prior to the
------
anticipated closing of such Approved Sale or an Initial Investors Cash-Out
within 100 days following such Initial Investors Cash-Out.

     (d) If the event giving rise to the Holdings Notice is an anticipated
Approved Sale, the Holdings Notice shall state:  (i) the anticipated date of
closing of the Approved Sale, (ii) whether or not Holdings anticipates that the
Approved Sale will cause the vesting of the 40%

                                       5
<PAGE>

IRR Warrant or the 60% IRR Warrant and (iii) that certificates for the Warrant
Shares (or such other shares or consideration that may be received by a holder
of Warrant Shares upon the closing of such Approved Sale) will be delivered to
the Holder on the closing date of such Approved Sale, subject to the vesting of
such warrants, at the principal office of Holdings or such other place as may be
designated by Holdings in the Holdings Notice.

     (e) If the event giving rise to the Holdings Notice is an Initial Investor
Cash-Out, the Holdings Notice shall state:  (i) the amount received by the
Initial Investors in connection with the Initial Investors Cash-Out (ii) whether
or not the Initial Investors Cash-Out caused the 40% IRR Warrant or the 60% IRR
Warrant to vest and (iii) that, if such vesting occurred, certificates for the
Warrant Shares will be delivered to the Holder at the principal office of
Holdings or such other place as may be designated by Holdings in the Holdings
Notice.

     (f) With respect to an Approved Sale, if the Holdings Notice states that
Holdings anticipates that such event will cause the vesting of the 40% IRR
Warrant or the 60% IRR Warrant, the Holder shall notify Holdings on or before
five days prior to the anticipated closing date of such Approved Sale of such
Holder's exercise and, with respect to an Initial Investors Cash-Out, if the
Holdings Notice states that such event has caused the vesting of either of such
warrants, the Holder shall notify Holdings on or before five days following
receipt of the Holdings Notice of such Holder's exercise of this Warrant (the
"Notice Date") .  This Warrant shall be exercisable by the Holder in whole only,
------------
and not in part, by the surrender of this Warrant and delivery to Holdings on or
before the Notice Date of (i) a duly executed notice of exercise in the form of
Exhibit A (a "Notice of Exercise") and (ii) the Exercise Price for the Warrant
              ------------------
Shares, payable in cash or by wire transfer to a bank account designated by
Holdings.

     (g) This Warrant shall terminate automatically upon the closing of an
Approved Sale and this Warrant shall no longer be of any force or effect, unless
(i) provision is made in writing in connection with such transaction for the
continuance of this Warrant and for the assumption of this Warrant, or for the
substitution for this Warrant of a new Warrant covering the securities of a
successor entity or an affiliate thereof, with appropriate adjustments as to the
number and kind of securities and exercise price, in which event this Warrant
shall continue or be replaced, as the case may be, in the manner and under the
terms so provided; or (ii) the Board of Directors of Holdings shall provide in
writing for such adjustment as it deems appropriate in terms and conditions of
this Warrant, including without limitation (A) accelerating the vesting of this
Warrant and/or (B) providing for the cancellation of this Warrant and its
automatic conversion into the right to receive the securities, cash or other
consideration that the Holder would have been entitled to receive upon
consummation of an Approved Sale had Warrant Shares been issued and outstanding
immediately prior to the Approved Sale (net of the appropriate exercise price).

     (h) This Warrant shall expire on December 20, 2009, unless the Holder's
employment with Holdings or any of its Subsidiaries: (i) is terminated with
Cause or the Holder leaves such employment for any reason, in which case this
Warrant will expire 30 days after the Termination of Employment; or (ii) is
terminated without Cause, or due to death, Disability or Retirement, or the
Holder leaves for any reason and the Board of Directors of Holdings determines
that the Holder left such employment due to personal hardship, in which case
this Warrant will expire 90 days after the Termination of Employment.

                                       6
<PAGE>

     3.  RESERVATION OF SHARES.  Holdings shall at all times reserve for
         ---------------------
issuance and/or delivery upon exercise of this Warrant such number of shares of
its Class B Common Stock as shall be required for issuance and delivery upon
exercise of this Warrant.  If any shares of the Class B Common Stock are or
become listed on any national securities exchange or the Nasdaq National Market,
Holdings shall also list the Warrant Shares, as the case may be, on such
exchange or system, as the case may be, subject to notice of issuance.

     4.  FRACTIONAL SHARES.  Fractional shares or scrip representing fractional
         -----------------
shares may be issued upon the exercise of this Warrant.  Alternatively, Holdings
may, at its option, with respect to any fraction of a share issuable upon any
exercise hereof, pay to the Holder an amount in cash equal to such fraction
multiplied by the greater of (i) the initial Exercise Price per share or (ii)
the current market value of a Warrant Share.  The current market value of a
Warrant Share shall be determined as follows:

     (a) If Warrant Shares are listed on a national securities exchange or
admitted to unlisted trading privileges on such exchange or listed for trading
on the Nasdaq National Market, the current market value shall be the last
reported sale price of a Warrant Share on such exchange or system on the last
day prior to the date of exercise of this Warrant or if no such sale is made on
such day, the average closing bid and asked prices for such day on such exchange
or system;

     (b) If Warrant Shares are not so listed or admitted to unlisted trading
privileges, the current market value shall be the mean of the last reported bid
and asked prices for a Warrant Share reported by the National Quotation Bureau,
Inc. on the last day prior to the date of the exercise of this Warrant; or

     (c) If the Warrant Shares are not so listed or admitted to unlisting
trading privileges and bid and asked prices are not so reported, the current
market value shall be an amount reasonably determined by the Board of Directors
of Holdings.

     5.  NONTRANSFERABILITY.  This Warrant shall not be transferable by the
         ------------------
Holder except that the Holder may transfer this Warrant to (a) his or her
spouse, child, estate, personal representative, heir or successor (b) a trust
for the benefit of the Holder or his or her spouse, child or heir, or (c) a
partnership the partners of which consist solely of the Holder and/or his or her
spouse, child, heir, and/or successor (each, a "Permitted Transferee") and this
                                                --------------------
Warrant is exercisable, during the Holder's lifetime, only by him or her or his
or her spouse or child, or, in the event of the Holder's Disability, his or her
guardian or legal representative.  More particularly (but without limiting the
generality of the foregoing), this Warrant may not be assigned, transferred
(except as aforesaid), pledged or hypothecated in any way (whether by operation
of law or otherwise), and shall not be subject to execution, attachment or
similar process.  Any assignment, transfer, pledge, hypothecation or other
disposition of this Warrant contrary to the provisions hereof, and the levy of
any attachment or similar process upon this Warrant that would otherwise effect
a change in the ownership of this Warrant, shall terminate this Warrant;
provided, however, that in the case of the involuntary levy of any attachment or
similar involuntary process upon this Warrant, the Holder shall have thirty (30)
days after notice thereof to cure such levy or process before this Warrant
terminates.

                                       7
<PAGE>

     6.  RIGHTS OF THE HOLDER.  Holder shall not, by virtue hereof, be entitled
         --------------------
to any rights of a stockholder in Holdings, either at law or equity (including,
without limitation, any rights to dividends) and the rights of the Holder with
respect to the shares of Class B Common Stock purchasable pursuant to this
Warrant are limited to those expressed in this Warrant and are not enforceable
against Holdings except to the extent set forth herein.

     7.  ANTI-DILUTION PROVISIONS.  So long as this Warrant shall be
         ------------------------
outstanding, the Exercise Price in effect at any time and the number and kind of
securities purchasable upon the exercise of this Warrant shall be subject to
adjustment from time to time upon the happening of certain events.  In case
Holdings shall, with respect to its Class B Common Stock (or Common Stock issued
upon conversion thereof):  (i) declare a dividend or make a distribution on its
outstanding shares of common stock in shares of such stock, (ii) subdivide or
reclassify its outstanding shares into a greater number of shares or (iii)
combine or reclassify its outstanding shares into a smaller number of shares,
then the Exercise Price and the number of Warrant Shares purchasable upon
exercise of this Warrant in effect at the time of the record date for such
dividend or distribution, or the effective date of such subdivision, combination
or reclassification, shall be appropriately adjusted as of the effective date of
such dividend, or distribution, subdivision, combination or reclassification, to
reflect such event.  Irrespective of any adjustments in the Exercise Price or
the number or kind of Warrant Shares purchasable upon exercise of this Warrant,
Warrants therefore or thereafter issued may continue to express the same price
and number and kind of shares as are stated in this Warrant initially issued.

     8.  OFFICER'S CERTIFICATE.  Whenever the Exercise Price shall be adjusted
         ---------------------
as required by the provisions of the foregoing, Holdings shall forthwith file in
the custody of its Secretary or an Assistant Secretary at its principal office
and with its stock transfer agent, if any, a certificate of Holdings' Chief
Financial Officer showing the adjusted Exercise Price and number of Warrant
Shares determined as herein provided, setting forth in reasonable detail the
facts requiring such adjustment.  Each such officer's certificate shall be made
available at all reasonable times for inspection by the Holder or any holder of
this Warrant, and Holdings shall, forthwith after each such adjustment, mail, by
certified mail, a copy of such certificate to the Holder or any such holder.

     9.  NOTICES TO WARRANT HOLDERS.  So long as this Warrant shall be
         --------------------------
outstanding, (i) if Holdings shall declare any dividend or make any distribution
upon the Class B Common Stock or (ii) if Holdings shall generally offer to the
holders of the Class B Common Stock for subscription or purchase by them of any
shares of any class of Holdings' capital stock or any other rights to purchase
shares of Holdings' capital stock, then in any such case, Holdings shall cause
notice to be given to the Holder of this Warrant, at least 10 days prior to the
date specified in (x), (y) or (z) below, as the case may be, notice which shall
contain a brief description of the proposed action and stating the date on which
(x) a record is to be taken for the purpose of such dividend, distribution or
offer for subscription or purchase, (y) such reorganization, reclassification,
consolidation, merger, sale, lease, transfer, dissolution, liquidation or
winding up is to take place and the date, if any, that is to be fixed, as of
which the holders of the Class B Common Stock or other capital stock of Holdings
shall receive cash or other property deliverable upon such reclassification,
reorganization, consolidation, merger, conveyance, dissolution, liquidation or
winding up, or (z) the date by which holders of

                                       8
<PAGE>

the Class B Common Stock must elect to participate in the purchase of securities
by Holdings pursuant to the offering referred to in clause (ii) above.

     10.  RECLASSIFICATION OR REORGANIZATION.  Subject to Section 2(g), in case
          ----------------------------------
of any reclassification, conversion or capital reorganization of outstanding
shares of the Class B Common Stock of Holdings, Holdings shall, as a condition
precedent to such reclassification, conversion or capital reorganization, cause
effective provisions to be made so that the Holder shall have the right
thereafter by exercising this Warrant at any time prior to the expiration of
this Warrant, to purchase the kind and amount of shares of stock and other
securities and property receivable upon such reclassification, conversion or
capital reorganization which would have been deliverable to the Holder of this
Warrant on the effective date of the reclassification, conversion or
reorganization had the Holder exercised this Warrant immediately prior to the
event described in this Section 10.  Any such provision shall include provision
for subsequent adjustments which shall be as nearly equivalent as may be
practicable to the adjustments provided for in this Warrant.  The foregoing
provisions of this Section 10 shall similarly apply to successive
reclassifications, conversions or capital reorganizations of shares of the Class
B Common Stock.

     11.  SECURITIES LAW COMPLIANCE.
          -------------------------

     (a) The Holder of this Warrant, by acceptance hereof, acknowledges that
this Warrant and the Warrant Shares to be issued upon exercise hereof are being
acquired solely for the Holder's own account and not as a nominee for any other
party, and for investment, and that the Holder will not offer, sell, transfer,
assign or otherwise dispose of this Warrant or any Warrant Shares to be issued
upon exercise hereof except under circumstances that will not result in a
violation of the Securities Act, or any state securities laws.  Upon exercise of
this Warrant, the Holder shall, if requested by Holdings, that the shares of
Class B Common Stock so purchased are being acquired solely for the Holder's own
account and not as a nominee for any other party, for investment, and not with a
view toward distribution or resale.

     (b)  If deemed necessary by counsel to Holdings, this Warrant and all
Warrant Shares issued upon exercise hereof shall be stamped or imprinted with
legends, including without limitation legends setting forth the restrictions on
transfer arising under applicable federal and state securities laws.

     12.  REPRESENTATIONS OF THE HOLDER.
          -----------------------------

     (a) The Holder represents and warrants to Holdings that it has substantial
knowledge, skill and experience in making investment decisions of the type
represented by this Warrant and the Warrant Shares.  It is capable of evaluating
the risk of its investment in this Warrant and the Warrant Shares and is able to
bear the economic risk of such investment, including the risk of losing the
entire investment, that it is acquiring this Warrant and the Warrant Shares for
its own account, and that this Warrant and the Warrant Shares are being acquired
by it for investment and not with a present view to any distribution thereof in
violation of applicable securities law.  If the Holder should in the future
decide to dispose of any of this Warrant and the Warrant Shares, it is
understood that it may do so only in compliance with the Securities Act and

                                       9
<PAGE>

applicable state securities laws.  The Holder represents and warrants that it is
an "accredited investor" as defined in Rule 501(a) under the Securities Act.

     (b) The Holder understand that (i) this Warrant and the Warrant Shares have
not been registered under the Securities Act by reason of their issuance in a
transaction exempt from the registration requirements of the Securities Act (ii)
this Warrant and the Warrant Shares must be held indefinitely unless a
subsequent disposition thereof is registered under the Securities Act and
applicable state securities laws or is exempt from such registration (and
evidence satisfactory to Holdings is provided by such Holder of the availability
of such exemptions, including the delivery to Holdings of opinions of counsel to
such Holder, which opinions and counsel satisfactory to Holdings), and (iii)
this Warrant and the Warrant Shares may bear a legend to such effect.

     13.  LOSS, THEFT, DESTRUCTION.  Upon receipt by Holdings of evidence
          ------------------------
reasonably satisfactory to it of the loss, theft, destruction or mutilation of
this Warrant, and, in case of loss, theft or destruction, of an indemnity letter
(reasonably satisfactory to Holdings) of an institutional Holder of this Warrant
or in other cases, of an indemnity letter or other security reasonably
satisfactory to Holdings, and upon surrender and cancellation of this Warrant,
if mutilated, Holdings will make and deliver a new Warrant of like tenor and
date in lieu of this Warrant.  This Warrant shall be promptly canceled by
Holdings upon the surrender hereof in connection with any such transfer or
replacement.  The Holder shall pay all expenses, taxes and other charges payable
in connection with the preparation, execution and delivery of any such
replacement Warrant.

     14.  AMENDMENTS.  Neither this Warrant nor any term hereof may be changed,
          ----------
waived, discharged or terminated without the prior written consent of the
Holder.

     15.  GOVERNING LAW.  This Agreement shall be governed by and construed
          -------------
under the laws of the New York.

     16.  NOTICES.  All notices, requests, demands and other communications
          -------
pursuant to this Warrant shall be in writing and shall be deemed to have been
duly given if personally delivered, telexed or telecopied to, or, if mailed,
when received by, the other party at the following addresses (or at such other
address as shall be given in writing by either party to the other):

     If to Holdings to:

          IWO Holdings, Inc..
          c/o Gibson, Dunn & Crutcher LLP
          200 Park Avenue, 47th Floor
          New York, New York 10166
          Attention:  Sean P. Griffiths, Esq.

          With a copy to:

          Gibson, Dunn & Crutcher LLP
          200 Park Avenue, 47th Floor

                                       10
<PAGE>

          New York, New York 10166-0193
          Attention:  Sean P. Griffiths, Esq.

     If to the Holder, to the following address (or to such other address as may
be provided on a Transfer Form):

          _________________

          _________________

          _________________

                                       11
<PAGE>

     IN WITNESS WHEREOF, Holdings has caused this Warrant to be executed by its
officer thereunto duly authorized.

Dated:

IWO HOLDINGS, INC.

________________________

By:

Title:
<PAGE>

                                   EXHIBIT A

                               NOTICE OF EXERCISE

                                                           _______________,  ___

To:  IWO Holdings, Inc.

     The undersigned, pursuant to the provisions set forth in IWO Holdings, Inc.
Warrant to Purchase Shares of Class B Stock, hereby agrees to purchase
_______________ shares of Class B Common Stock and makes payment herewith in
full therefor at the Exercise Price of $_______________ in the following form:
_______________.  Certificates for such shares shall be issued in the name of
and delivered to the undersigned, unless otherwise specified by written
instructions, signed by the undersigned and accompanying this notice.

Signature:
          -------------------
Printed Name:
             ----------------
Address:
        ---------------------

-----------------------------

                                   EXHIBIT B

                                 TRANSFER FORM

     FOR VALUE RECEIVED __________________ hereby sells, assigns and transfers
[all/__%] of the rights of the undersigned under IWO Holdings, Inc. Warrant to
Purchase Shares of Class B Stock, with respect to the number of Warrant Shares
covered thereby unto:

Name of Transferee                                     Address
------------------                                     -------

     The undersigned further hereby irrevocably constitutes and appoints
________________ its attorney-in-fact to make such transfers on the books and
records of Holdings maintained for such purpose, with full power of
substitution.

Dated:
      -------------------------
Signature:
          ---------------------
Printed Name:
             ------------------
Address:
        -----------------------

-------------------------------

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00011-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00011-of-00352.parquet"}]]