Document:

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                                                                   EXHIBIT 10.16

January 14, 2002

Mr. John E. Calonico, Jr.
301 Laurel Avenue
Milbrae, CA  94030

Dear John:

I am pleased to offer you a position with iMANAGE, INC. (the "Company") as Vice
President and Chief Financial Officer. You will report directly to Mahmood
Panjwani, President and Chief Executive Officer, and your anticipated start date
will be January 14, 2002.

Should you decide to join us, your compensation package would be as follows:

    1.  You will receive a monthly salary of $16,666.66 ($200,000 per year),
        which will be paid semi-monthly in accordance with the Company's normal
        payroll procedures (the "Base Salary"). You will also receive a
        guaranteed bonus of $25,000 (the "Guaranteed Bonus") in the first year
        of employment, which shall be paid semi-monthly with your Base Salary.
        Your Base Salary and Guaranteed Bonus for calendar year 2003 and
        subsequent years will be no lower than calendar year 2002.

    2.  You will be eligible for an annual bonus of up to 40% of Base Salary
        (the "Annual Bonus"), which shall be payable upon achievement of goals
        as may be defined from time to time in the annual Executive Bonus Plan
        established by the iManage Board of Directors. In your first year of
        employment, the Guaranteed Bonus shall be subtracted from any Annual
        Bonus payments.

    3.  I will recommend that the Board of Directors grant you an option to
        purchase 250,000 shares of iMANAGE, INC. common stock (the "Basic
        Option"). The exercise price for the option to purchase the first 75,000
        shares under the Basic Option shall be $4.00 (four dollars) per share.
        The exercise price for the remaining 175,000 optioned shares under the
        Basic Option shall be equal to the then current fair market value of
        common stock, as determined by the Board of Directors. Subject to your
        continued employment with the Company, these options will vest ratably
        on a monthly basis over 4 years (i.e. 1/48 per month), with a cliff of 6
        months. You may immediately exercise all options under the Basic Option
        at any time after the grant date by executing a full recourse promissory
        note in a form as may be required in the Company's reasonable
        discretion.

    4.  In addition to the Basic Option, I will recommend to the Board that you
        be granted an option to purchase 50,000 shares (the "Bonus Option")
        which will vest ratably on a monthly basis over 6 years (i.e. 1/72 per
        month), with a two year cliff; provided, however, that upon achievement
        of bonus goals established by the Board of Directors for the 2002
        calendar year, the vesting and exercisability of 12,500 shares of stock
        shall accelerate for each quarter in which the bonus goals are achieved
        (the "Accelerated Shares") as follows: 1/8 of the Accelerated Shares
        will vest on July 1, 2002, and for each full month of your service
        thereafter, an additional 1/48 of the Accelerated Shares shall vest. The
        exercise price for the shares under the Bonus Option shall be equal to
        the then current fair market value of common stock, as determined by the
        Board of Directors. You may immediately exercise all shares under Bonus
        Option at any time after the grant date by executing a full recourse
        promissory note in a form as may be required in the Company's reasonable
        discretion.

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    5.  In addition, the Company will provide you with the same benefits it
        provides to its other executive-level employees, including but not
        limited to health and medical benefits, paid vacation, 401(k) plan and
        similar benefits and plans as may be adopted by the Company from time to
        time.

    6.  In the event of your Constructive Termination (as defined below) within
        twelve (12) months following a Transfer of Control (as such term is
        defined in Section 8.1(b) of the Company's Stock Option Plan), and
        provided you execute a release in the form attached hereto as Exhibit A,
        the vesting and exercisability of the outstanding stock options granted
        to you in items 3 and 4 above and any subsequent option grants will
        immediately accelerate in an amount equal to fifty percent (50%) of the
        remaining unvested options as of the date of the Constructive
        Termination.

    "Constructive Termination" means a termination of your employment by the
        Company (or any successor entity) other than for Cause (within 30 days
        following the occurrence of such Cause), or your resignation from the
        Company (or any successor entity) within thirty (30) days following an
        event of Good Reason.

    "Cause" means (A) material willful misconduct or gross negligence in
        performance of your duties hereunder, including your refusal to comply
        in any material respect with the legal directives of the Company's board
        of Directors; (B) dishonest or fraudulent conduct, a deliberate attempt
        to do an injury to the Company, or conduct that materially harms the
        Company or is materially detrimental to the Company's reputation,
        including any felony conviction; or (C) a material breach of any element
        of the Company's Employee Inventions and Proprietary Rights Assignment
        Agreement, including without limitation, theft or other material
        misappropriation of the Company's proprietary information.

    "Good Reason" means (A) a material adverse change in your position,
        including but not limited to a change in title/position (including to
        whom you report), responsibilities, required geographic location (more
        than 25 miles from the Company's current location); or (B) a reduction
        of your base salary and incentive plan.

    7.  In event of your Constructive Termination, Company shall: (A) pay to you
        a severance payment equal to six (6) months of Base Salary, payable over
        each ordinary pay-period for such period; (B) provide you with continued
        coverage of the Company's standard benefits package for a period of six
        (6) months from the date of Constructive Termination; and (C)
        immediately accelerate the vesting and exercisability of the stock
        options granted to you in items 3 and 4 above (and any additional grants
        which may have been provided) a period of six (6) months; provided,
        however, that this clause (C) shall not apply in the event that such
        Constructive Termination occurs within twelve (12) months following a
        Transfer of Control, in which case the first paragraph of item 6 above
        shall apply in its stead.

    8.  The Company shall reimburse you for all reasonable travel, entertainment
        and other expenses incurred by you in performing your responsibilities
        in accordance with the Company's reimbursement policy.

    9.  During your employment, the Company will provide you with Director and
        Officer errors and omissions insurance and ERISA fiduciary insurance at
        levels no less than those offered to its other executive-level officers.

    10. The Company and you will mutually agree on the timing and content of any
        press releases or announcements regarding your joining the Company and
        neither party will make any announcement or press release regarding such
        without the other's prior approval.

IF YOU CHOOSE TO ACCEPT THIS OFFER, YOUR EMPLOYMENT WITH THE COMPANY WILL BE
VOLUNTARILY ENTERED INTO AND WILL BE FOR NO SPECIFIED PERIOD. AS A RESULT, YOU
WILL BE FREE TO RESIGN AT ANY TIME, FOR ANY REASON OR FOR NO REASON, AS YOU DEEM
APPROPRIATE SIMPLY BY NOTIFYING THE COMPANY. THE COMPANY WILL HAVE A SIMILAR
RIGHT AND MAY CONCLUDE ITS EMPLOYMENT RELATIONSHIP WITH YOU AT ANY TIME, WITH OR
WITHOUT CAUSE.

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For purposes of federal immigration law, you will be required to provide to the
Company documentary evidence of your identity and eligibility for employment in
the United States. Such documentation must be provided to us within three (3)
business days of your start date, or our employment relationship with you may be
terminated.

In the event of any dispute or claim relating to or arising out or our
employment relationship, you and the Company agree that all such disputes shall
be fully and finally resolved by binding arbitration conducted by the American
Arbitration Association in San Francisco, California. HOWEVER, we agree that
this arbitration provision shall not apply to any dispute or claim relating to
or arising out of the misuse or misappropriation of the Company's trade secrets
or proprietary or confidential information.

You will be required to sign an Employee Inventions and Proprietary Rights
Assignment Agreement as a condition of your employment. This letter, along with
any agreements relating to proprietary rights between you and the Company, set
forth the terms of your employment with the Company and supersede any prior
representations or agreements, whether written or oral. This letter may not be
modified or amended except by a written agreement, signed by the Company and by
you.

To indicate your acceptance of the Company's offer, please sign and date this
letter in the space provided below and return it to me. A duplicate original is
enclosed for your records.

This offer of employment will expire at 5:00 p.m. on January 18, 2001.

We look forward to working with you at iMANAGE, INC. Welcome aboard!

Sincerely,

Mahmood Panjwani
President and CEO
iManage, Inc.

AGREED TO AND ACCEPTED

 /s/ John E. Calonico, Jr.
-----------------------------------
John E. Calonico, Jr.<PAGE>

                                                                   EXHIBIT 10.38

                               TWENTIETH AMENDMENT
                                       TO
                    CONVERTIBLE DEBENTURE PURCHASE AGREEMENT

        THIS TWENTIETH AMENDMENT TO CONVERTIBLE DEBENTURE PURCHASE AGREEMENT
(the "Amendment") is entered into as of March 6, 2002, by and between DISC,
Inc., a California corporation (the "Company"), and MK GVD Fund (the
"Purchaser").

                                R E C I T A L S:

        A. WHEREAS on March 29, 1996 the Company and Purchaser entered into a
Convertible Debenture Purchase Agreement pursuant to which the Company agreed to
sell, and Purchaser agreed to purchase, an aggregate of $1,400,000 in principal
amount of Convertible Debentures, each convertible into shares of the Company's
Preferred Stock, which Agreement was amended as of December 31, 1996, April 11,
1997, December 31, 1997, March 27, 1998, June 30, 1998, September 25, 1998,
December 31, 1998, March 30, 1999, June 30, 1999, September 30, 1999, December
31, 1999, March 31, 2000, June 30, 2000, September 30, 2000, December 29, 2000,
March 30, 2001, June 29, 2001, September 28, 2001 and December 31, 2001 to
increase the aggregate amount of Convertible Debenture to be purchased
thereunder to $16,430,000.

        B. The Company and Purchaser now seek to amend the Agreement to increase
the total amount of Convertible Debentures which Purchaser agrees to purchase
thereunder.

        NOW, THEREFORE, for good and valuable consideration, receipt of which is
hereby acknowledged, and in consideration of the mutual covenants set forth
herein, the parties hereto agree as follows:

        1. DEFINITIONS. Unless otherwise defined herein, capitalized terms used
in the Amendment shall have the same meanings ascribed to them in the
Convertible Debenture Purchase Agreement.

        2. AMENDMENT TO CONVERTIBLE DEBENTURE PURCHASE AGREEMENT. Section 1.1(a)
of the Convertible Debenture Purchase Agreement is hereby amended to provide
that Purchaser agrees to purchase, and the Company agrees to issue and sell, an
aggregate of $16,455,000 in principal amount of Convertible Debentures, each in
the form and having the terms and conditions set forth in the amended Exhibit B
attached hereto.

        3. ENTIRE AGREEMENT; AMENDMENT. The Convertible Debenture Purchase
Agreement, as amended by this Amendment, constitutes the full and complete
agreement and understanding between the parties hereto regarding the subject
matter of the Convertible Debenture Purchase Agreement and shall supersede all
prior communications, representations, understandings or agreements, if any,
whether oral or written, concerning the subject matter contained in the
Convertible Debenture Purchase Agreement, as so amended, and that no provision
of the Convertible Debenture Purchase Agreement, as so amended, may be modified,
amended, waived or discharged, in whole or in part, except in accordance with
its terms.

        4. FORCE AND EFFECT. Except as modified by this Amendment, the terms and
provisions of the Convertible Debenture Purchase Agreement are hereby ratified
and confirmed and are and shall remain in full force and effect. Should any
inconsistency arise between this Amendment and the Convertible Debenture
Purchase Agreement as to the specific matters which are the subject of this
Amendment, the terms and conditions of this Amendment shall control. This
Amendment shall be construed to be part of the Convertible

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Debenture Purchase Agreement and shall be deemed incorporated into the
Convertible Debenture Purchase Agreement by this reference.

        5. COUNTERPARTS. This Amendment may be executed in one or more
counterparts, each of which shall be an original but all of which together shall
constitute one instrument.

        IN WITNESS WHEREOF, the Company has caused this Amendment to be executed
in duplicate on its behalf by its duly authorized officer and Purchaser has also
executed this Amendment in duplicate, all as of the day and year indicated
above.

                                  DISC, INC.
                                  a California corporation

                                  By: /s/ Henry Madrid
                                      ------------------------------------------
                                      Henry Madrid
                                      Chief Financial Officer

                                  PURCHASER:
                                  MK GVD FUND

                                  By: /s/ Michael Hoffman
                                      ------------------------------------------
                                      Michael Hoffman, General Partner

                                      -2-

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                                    EXHIBIT B

                   FORM OF SUBORDINATED CONVERTIBLE DEBENTURE

THE SECURITIES EVIDENCED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE
SECURITIES ACT OF 1933 AND HAVE BEEN TAKEN FOR INVESTMENT PURPOSES ONLY AND NOT
WITH A VIEW TO THE DISTRIBUTION THEREOF, AND SUCH SECURITIES MAY NOT BE SOLD OR
TRANSFERRED UNLESS THERE IS AN EFFECTIVE REGISTRATION STATEMENT OR REGULATION A
NOTIFICATION UNDER SUCH ACT COVERING SUCH SECURITIES OR THE ISSUER CORPORATION
RECEIVES AN OPINION OF COUNSEL (WHICH MAY BE COUNSEL FOR THE ISSUER CORPORATION)
STATING THAT SUCH SALE OR TRANSFER IS EXEMPT FROM THE REGISTRATION AND
PROSPECTUS DELIVERY REQUIREMENTS OF SUCH ACT.

                                   DISC, INC.
                            A CALIFORNIA CORPORATION

                       SUBORDINATED CONVERTIBLE DEBENTURE

No. ________                                                 ____________, 20___

        FOR VALUE RECEIVED, DISC, INC., a California corporation (the
"Company"), hereby promises to pay to MK GVD FUND, a California limited
partnership (hereinafter referred to as the "Holder"), or registered assigns, on
the day on which this Debenture is issued by the Company (the "Maturity Date"),
subject to conversion as described below, the principal sum of ____________
Dollars ($________), or such part thereof as then remains unpaid or unconverted.
This Debenture shall not bear interest.

        1. Other Agreements.

                (a) Purchase Agreement. This Debenture is issued pursuant to and
is entitled to the benefits and subject to the conditions of that certain
Convertible Debenture Purchase Agreement of even date herewith, among the
Company, Holder and other Investors as defined therein, as the same may be
amended from time to time (the "Purchase Agreement"), and Holder, and its
successors and assigns, by its acceptance hereof, agrees to be bound by the
provisions of the Purchase Agreement, a copy of which may be inspected by Holder
at the principal office of the Company.

                (b) Registration Rights Agreement. This Debenture is entitled to
the benefits and subject to the conditions of that certain Registration Rights
Agreement dated March 29, 1996, among the Company and Holder, as the same may be
amended from time to time (the "Registration Rights Agreement"), and Holder, and
its successors and assigns, by its acceptance hereof, agrees to be bound by the
provisions of the Registration Rights Agreement, a copy of which may be
inspected by Holder at the principal office of the Company.

<PAGE>

        2. Conversion.

                (a) Mandatory Conversion Into Preferred Stock and Warrants. This
Debenture shall be converted into Units (as hereinafter defined) on the Maturity
Date by the surrender of this Debenture in the manner specified in Section 3(c)
below. The number of Units into which this Debenture shall be converted shall
equal the principal amount of the Debenture being converted divided by the
"Conversion Price" (as hereinafter defined). Each Unit shall consist of (i) a
number of shares of the Company's Preferred Stock, of a series designated by the
Company having rights and preferences pari passu with those of the Company's
Series D, Series E, Series F, Series G, Series H, Series I, Series J, Series K,
Series L, Series M, Series N, Series O, Series P, Series Q, Series R, Series S,
Series T, Series U, Series V, Series W, Series X, Series Y, Series Z, Series AA,
Series BB, Series CC, Series DD, Series EE and Series FF Preferred Stock (the
"Shares") equal to the quotient obtained by dividing one (1) by the number of
shares of Common Stock into which each such Share is then convertible and (ii) a
warrant (the "Warrant") to purchase a number of shares of the Company's Common
Stock equal to twenty-five percent (25%) of the number of shares of Common Stock
into which each such Share is convertible, which Warrant shall has an exercise
price equal to ________% of the Conversion Price, shall be exercisable for five
(5) years following the Maturity Date and shall be substantially in the form
attached to the Purchase Agreement as Exhibit A.

                (b) Conversion Price. The "Conversion Price" shall be
eighty-five percent (85%) of the average closing price per share of the
Company's Common Stock as quoted on the Nasdaq Small Cap Market for the five (5)
trading days ended three (3) days prior to the Maturity Date.

                (c) Mechanics of Conversion. On or before the Maturity Date, the
holder shall surrender the certificate or certificates for this Debenture, duly
endorsed, at the Company's principal corporate office, and shall state therein
the name or names in which the certificate or certificates for shares of
Preferred Stock are to be issued. The Company shall, as soon as practicable
thereafter, issue and deliver at such office to such Holder, or to the nominee
or nominees of such Holder, a certificate or certificates for the number of
shares of Preferred Stock to which such Holder shall be entitled as aforesaid.
Such conversion shall be deemed to have been made immediately prior to the close
of business on the Maturity Date, and the person or persons entitled to receive
the shares of Preferred Stock issuable upon such conversion shall be treated for
all purposes as the record holder or holders of such shares of Preferred Stock
as of such date.

                (d) No Impairment. The Company will not, by amendment of its
Certificate of Incorporation or through any reorganization, recapitalization,
transfer of assets, consolidation, merger, dissolution, issue or sale of
securities or any other voluntary action, avoid or seek to avoid the observance
or performance of any of the terms to be observed or performed hereunder by the
Company but will at all times in good faith assist in the carrying out of all
the provisions of this Section 3 and in the taking of all such action as may be
necessary or appropriate in order to protect the conversion rights of the
holders of the Debentures against impairment.

                (e) Taxes in Conversion. The issue of share certificates on
conversion of this Debenture shall be made without charge to the converting
Holder for any tax in respect of the issue thereof. The Company shall not,
however, be required to pay any tax which may be payable in respect of any
transfer involved in the issue and delivery of shares in any name other than
that of the Holder, and the Company shall not be required to issue or deliver
any certificate in respect of such shares unless and until the person or persons
requesting the issuance thereof shall have paid to the Company the amount of
such tax or shall have established to the satisfaction of the Company that such
tax has been paid.

                (f) Reservation of Conversion Securities. The Company agrees
that the Company will at all times have authorized and reserved, and will keep
available, solely for issuance or delivery upon the

                                      -2-

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conversion of this Debenture, the shares of Preferred Stock and other securities
and properties as from time to time shall be receivable upon the conversion of
this Debenture.

                (g) No Rights as Stockholders. Prior to the Conversion of this
Debenture, the Holder of this Debenture shall not be entitled to any rights of a
stockholder of the Company, including, without limitation, the right to vote, to
receive dividends or other distributions or to exercise any pre-emptive rights,
and shall not be entitled to receive any notice of any proceedings of the
Company, except as provided herein or in the Purchase Agreement or as otherwise
agreed.

        3. Merger, Consolidation.

                (a) Acceleration on Merger, Consolidation. In the event of (i)
any consolidation or merger of the Company with or into any other corporation or
other entity or person, or any other corporate reorganization in which the
Company shall not be the continuing or surviving entity, or any transaction or
series of related transactions by the Company in which in excess of 50% of the
Company's voting power is issued for the purpose of combining with or
acquisition by one or more corporations or other entities or persons; or (ii) a
sale, conveyance or disposition of all or substantially all of the assets of the
Company, then the principal and accrued interest on this Debenture shall be due
and payable at the closing of any such transaction.

                (b) Notices. The Company shall give each Debenture holder
written notice of such impending transaction not later than twenty (20) days
prior to the stockholders' meeting called to approve such transaction, or twenty
(20) days prior to the closing of such transaction, whichever is earlier. The
first of such notices shall describe the material terms and conditions of the
impending transaction and the provisions of this Section 4 and the Company shall
thereafter give such holders prompt notice of any material changes. The
transaction shall in no event take place sooner than twenty (20) days after the
Company has given the first notice provided for herein or sooner than ten (10)
days after the Company has given the notice provided for herein of any material
changes, provided, however, that such periods may be shortened upon the written
consent of the holders of the majority of the principal amount of Debentures
then outstanding.

        4. Transfer. Subject to the restrictions and limitations set forth in
the Purchase Agreement, upon surrender of this Debenture for transfer or
exchange, a new Debenture or new Debentures of the same tenor, dated the date to
which interest has been paid on the surrendered Debenture and in an aggregate
principal amount equal to the unpaid principal amount of the Debenture so
surrendered, will be issued to and registered in the name of the transferee or
transferees. The Company may treat the person in whose name this Debenture is
registered as the owner hereof for the purpose of receiving payments and for all
other purposes.

        5. Debenture Register. This Debenture is transferable only upon the
books of the Company which it shall cause to be maintained for such purpose. The
Company may treat the registered holder of this Debenture as he or it appears on
the Company's books at any time as the Holder for all purposes.

        6. Loss, Etc., of Debenture. Upon receipt of evidence satisfactory to
the Company of the loss, theft, destruction or mutilation of this Debenture, and
of indemnity reasonably satisfactory to the Company if lost, stolen or
destroyed, and upon surrender and cancellation of this Debenture if mutilated,
and upon reimbursement of the Company's reasonable incidental expenses, the
Company shall execute and deliver to the Holder a new Debenture of like date,
tenor and denomination.

        7. Amendment, Waiver Etc., By Holders. The terms of this Debenture may
be amended or waived upon the written consent of the Company and the Holder.

                                      -3-

<PAGE>

        This Debenture shall be governed by and construed in accordance with the
laws of the State of California.

        The Company hereby waives presentment, demand, notice of nonpayment,
protest and all other demands and notices in connection with the delivery,
acceptance, performance or enforcement of this Debenture. If an action is
brought for collection under this Debenture, the Holder shall be entitled to
receive all costs of collection, including, but not limited to, its reasonable
attorneys' fees.

                                DISC, INC.
                                a California Corporation

                                By:
                                   ---------------------------------------------
                                   Henry Madrid
                                   Chief Financial Officer

                                      -4-

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