<PAGE>

EX-10.1
                              EMPLOYMENT AGREEMENT

         This Employment Agreement ("Agreement") is made as of October 13, 2000
by and between I-Many, Inc., a Delaware corporation having its principal place
of business at 537 Congress Street, 5th Floor, Portland, ME 04101-3353 (the
"Company") and Leigh Powell, a resident of 744 Signal Light Road, Moorestown, NJ
08057 ("Executive").

         WHEREAS, the Company desires to employ Executive, and Executive desires
to be employed by the Company, and the Board of Directors of the Company (the
"Board of Directors") has determined that it is in the best interests of the
Company and its shareholders to formalize the employment relationship pursuant
to this Agreement.

         NOW, THEREFORE, in consideration of the mutual covenants and promises
contained herein, and other good and valuable consideration, the receipt and
sufficiency of which are acknowledged by the parties, the Company and the
Executive agree as follows:

1.       EMPLOYMENT.

                  1.1 POSITION. The Company agrees to employ Executive in the
position(s) stated in EXHIBIT A to this Agreement. Executive accepts employment
with the Company in such capacity and agrees to serve the Company faithfully,
diligently and to the best of his or her ability pursuant to the
responsibilities and goals set forth in the position description attached to
this Agreement as EXHIBIT A. Executive agrees to assume other roles and
responsibilities as may be assigned from time to time by the Board of Directors,
and which are consistent with the Executive's title and position. During the
course of Executive's employment with the Company, Executive agrees to devote
his or her full business time, energy, attention, and skill to such employment
and agrees not to, directly or indirectly, engage or participate in, or become
employed by, or become a director, officer, or partner of, or provide services
for compensation to or in connection with, any business activity that would be
considered competitive with the business of the Company or which conflicts or
interferes with the performance of Executive's obligations under this Agreement
without the express written consent of the Board of Directors.

                  1.2 EMPLOYMENT TERM. Executive's employment with the Company
shall be at will and, subject to the terms and conditions herein, this agreement
shall be terminable accordingly.

2.       COMPENSATION.

                 2.1 SALARY. The Company shall compensate Executive as set forth
on EXHIBIT A hereto subject to all standard employment deductions. The Base
Salary (as defined therein) shall be paid to Executive in accordance with the
Company's normal payroll practices. Executive's Base Salary may be increased
(but not decreased) annually at the discretion of the Board of Directors.


<PAGE>
                 2.2  BONUS PLAN.

                  (a) During the terms of his or her employment, Executive shall
                      be a participant in a discretionary, performance-based
                      bonus program, the terms of which, for an initial,
                      12-month period, shall be as stated in the attached
                      EXHIBIT B, and the remainder of which shall be as
                      determined subsequently by the Board of Directors or a
                      Compensation Committee thereof. The performance related
                      bonus shall be subject to all standard employment
                      deductions.

                  (b) In addition, Executive, provided that he is employed in
                      good standing by the Company on January 1, 2002, shall
                      receive a direct stock grant on January 2, 2002 of 100,000
                      shares of Company's common stock provided that the average
                      of the two highest Thirty-Day Averages ending on December
                      31, 2001, is equal to or greater than $20.00. For the
                      purposes of this Section 2.2, "Thirty-Day Average" means
                      the average over thirty consecutive days of the daily
                      closing prices of the Company's common stock (as listed in
                      the national edition of the Wall Street Journal) for each
                      of the three consecutive thirty-day periods commencing
                      ninety days prior to December 31 of any year.

                  (c) In addition, Executive, provided that he is employed in
                      good standing by the Company on January 1, 2003, shall
                      receive a direct stock grant on January 2, 2003 of 100,000
                      shares of Company's common stock provided that the average
                      of the two highest Thirty Day Averages ending on December
                      31, 2002, is equal to or greater than $30.00.

                  (d) Furthermore, if Executive is employed in good standing by
                      the Company on January 1, 2003 , or in the event he is
                      terminated (other than for Cause) at any time prior to
                      January 1, 2003, Executive shall receive a direct stock
                      grant of 100,000 shares of Company common stock.

                  2.3      STOCK OPTIONS.

                  (a) Vested Shares and Demand Note. The Executive agrees to
                      issue to the Company a demand note ("Demand Note") in an
                      amount not to exceed $1,000,000 (one million dollars), for
                      the sole purpose of the Executive exercising those stock
                      options vested at the time of the execution of this
                      Agreement and paying associated taxes. A copy of this
                      Demand Note and associated Pledge Agreement and Assignment
                      of Shares is attached as EXHIBIT C.

                  (b) Change of Control and Acceleration of Unvested Shares.
                      As a condition to the effectiveness of this Agreement,
                      Executive agrees to execute and deliver to the Company
                      Omnibus Amendment No. 1 to Incentive Stock Option (the
                      "ISO Amendment"). A copy of this ISO Amendment is attached
                      as EXHIBIT D.

         3.       OTHER BENEFITS.

                  3.1 BENEFIT PLANS. During the term of his or her employment,
Executive shall be entitled to participate in the Company's benefit plans and
programs, if any, made available generally to other employees or executives
similarly situated with the Company, including, but not limited to, medical and
health care plans, life insurance, disability and a 401(k) plan.

                  3.2 VACATION. Executive shall be entitled to three (3) weeks
of annual vacation, to be accrued and taken in accordance with the vacation
policy of the Company for similarly situated employees or executives, but which
in any case may be carried over from year to year to the extent not taken.

                                       2
<PAGE>

                  3.3 EXPENSES. The Company shall reimburse Executive for all
reasonable business expenses incurred by Executive in connection with, or
related to, the performance of Executive's duties, responsibilities or services
under this Agreement, upon Executive's presentation to the Company of expense
statements, vouchers or other supporting information, in accordance with Company
practices.

         4. NONDISCLOSURE, INVENTION AND NONCOMPETITION. As a condition to the
effectiveness of this Agreement, Executive agrees to execute and deliver to the
Company a nondisclosure, invention and noncompetition agreement (the
"Nondisclosure, Invention and Noncompetition Agreement"), a copy of which is
attached as EXHIBIT E.

5.       TERMINATION OF EMPLOYMENT.

                  5.1 MEANS OF TERMINATION. Subject to the terms and conditions
hereof, Executive's employment shall terminate:

                  (a) At the discretion of the either party at any time for any
                      reason;

                  (b) At the election of the Company for Cause, as such term is
                      defined herein; or

                  (c) Upon the death or permanent disability of Executive. As
                      used in this Agreement, the term "disability" shall mean
                      the inability of the Executive, due to a physical or
                      mental disability, for a period of 120 days, whether or
                      not consecutive, during any 360-day period to perform the
                      essential functions of the job, including the services
                      contemplated under this Agreement. A determination of
                      disability shall be made by a physician satisfactory to
                      both the Executive and the Company, PROVIDED THAT, if the
                      Executive and the Company do not agree on a physician, the
                      Executive and the Company shall each select a physician
                      and these two together shall select a third physician,
                      whose determination as to disability shall be binding on
                      all parties.

5.2      EFFECTS OF TERMINATION.

                  (a) Termination by the Company - Other than For Cause. If (i)
                      Executive's employment is terminated solely upon the
                      discretion of the Company pursuant to any reason other
                      than for Cause, as defined below; (ii) Executive resigns
                      because Executive's salary and/or potential bonus are
                      decreased below the Base Salary and initial bonus
                      identified in Section 2 above, or, in any later year,
                      below the Base Salary and/or potential bonus of the
                      previous year; (iii) Executive resigns because of a
                      material reduction in the level of Executive's job
                      responsibilities as set forth on EXHIBIT A, or is asked to
                      report to anyone other than the Board, or is demoted in
                      title, or (iv) the principal office in which the Executive
                      works is relocated without the Executive's consent to a
                      new location which lengthens the Executive's daily commute
                      by a distance in excess of 50 miles Executive shall be
                      entitled to the following:

                           (i)   SALARY AND ACCRUED VACATION. Pro-rated salary
                                 through the date of termination and accrued
                                 vacation earned but not yet paid and any earned
                                 but unpaid bonus, the availability and pro rata
                                 calculation of which shall be as determined at
                                 the discretion of the Board of Directors;

                           (ii)  SEVERANCE. The Company shall pay to Executive
                                 severance equal to nine (9) months of
                                 Executive's annualized base salary in effect as
                                 of the date of termination, payable in
                                 accordance with the Company's usual payroll
                                 practices. In addition, on the date of
                                 termination, Executive will be

                                       3
<PAGE>

                                 entitled to retain the stock grants received
                                 by such date in accordance with the
                                 provisions of Sections 2.2(a), (b) and (c).

                         (iii)   MEDICAL BENEFITS.  Executive's coverage under
                                 the company-sponsored group health insurance
                                 plan will continue through his or her
                                 termination date ("Termination Date"). After
                                 the Termination Date, the Company will continue
                                 to maintain Executive as a participant its
                                 health insurance plan as required under
                                 Consolidated Omnibus Budget Reconciliation Act
                                 of 1985 (often referred to as "COBRA"). The
                                 Company will pay Executive's cost of continued
                                 participation until the earlier of the end of
                                 the Noncompete period per Subsection 4 or
                                 Executive's commencement of any employment
                                 activity with any third party including, but
                                 not limited to, employment, consulting or
                                 independent contracting. In the event that
                                 Executive becomes covered by group health
                                 insurance while continuing his or her health
                                 insurance benefits under COBRA, the Company's
                                 obligation under this paragraph shall cease at
                                 that time.

                           (iv)  OTHER BENEFITS. Executive will be eligible to
                                 participate in the other benefit plans of the
                                 Company, at the Company's cost and as long as
                                 continued participation is permitted under the
                                 terms and conditions of such plans, until the
                                 earlier of the end of the Noncompete period per
                                 Subsection 4 or Executive's commencement of any
                                 employment activity including, but not limited
                                 to, employment, consulting or independent
                                 contracting.

                  (b) Termination by the Company - For Cause. The Company may
                      terminate Executive's employment for Cause at any time
                      upon thirty day's written notice without cure by the
                      Executive (in the case of (a) or (c) below, and without
                      prior written notice, in the case of (b) and (d) below. If
                      the Company terminates Executive's employment for Cause,
                      it shall have no further obligations to Executive under
                      this Agreement except for the payment of (i) awarded but
                      not yet paid bonus, (ii) accrued and unpaid salary and
                      vacation time, through the effective date of termination,
                      and (iii) unpaid expenses incurred by the Executive and
                      submitted in compliance with this Agreement. For purposes
                      of this Agreement, "Cause" for termination shall be deemed
                      to exist upon (a) a good faith finding by the Company of
                      refusal of Executive to perform his or her assigned
                      duties, consistent with the terms of this Agreement, for
                      the Company, (b) material dishonesty, (c) gross negligence
                      or gross misconduct in a manner that materially interferes
                      with Executive's job performance, or (d) the conviction of
                      Executive of, or the entry of a pleading of guilty or nolo
                      contendre by Executive to, any crime involving moral
                      turpitude or any felony.

                  (d) Termination through Death, Disability. In the event of
                      Executive's death while employed hereunder, Executive or
                      his or her legal representative(s) shall be entitled to
                      all amounts payable through the last date of employment,
                      including pro-rated salary earned but not yet paid and any
                      earned but unpaid bonus, the availability and pro rata
                      calculation of which shall be as determined at the
                      discretion of the Board of Directors.

         6.       MISCELLANEOUS.

                  6.1 SUCCESSORS AND ASSIGNS. This Agreement shall be binding
upon and shall inure to the benefit of the Company's successors in interest,
including, without limitation, successors through merger, consolidation, or sale
of substantially all of the Company's stock or assets, and shall be binding upon
Executive. The covenants

                                       4
<PAGE>

referenced in Sections 4 and 5.2 shall survive cessation of Executive's
employment with the Company, regardless of who causes the cessation and
regardless of the circumstances surrounding the cessation of employment.

                  6.2 NOTICE. All notices required or permitted to be given
under this Agreement shall be given in writing and shall be deemed sufficiently
given if delivered by hand or mailed by registered mail, return receipt
requested, to Executive's respective address and the principal offices of the
Company, both listed above, with copies to:

                  Alfred O. Powell, Esq.
                  131 Dawn Drive
                  Mt. Holly, NJ  08060

                  Bill Contente, Esq.
                  Lucash, Gesmer & Updegrove, LLP
                  40 Broad Street
                  Boston, Massachusetts 02109

By giving notice to the other party in accordance with this Paragraph, each
party may change the address at which it is to receive notices hereunder.

                  6.3 APPLICABLE LAW. This Agreement shall be governed by,
construed in, interpreted and enforced in accordance with the laws of the
Commonwealth of Massachusetts.

                  6.4 ARBITRATION. Except for any rights the Company may have to
apply to a court of competent jurisdiction for specific performance or
injunctive relief, including but not limited to enforcement of the
Nondisclosure, Invention and Noncompetition Agreement and provisions of Section
4, any other dispute arising or relating to the interpretation, validity, or
performance of this Agreement and any other dispute arising out of this
Agreement which cannot be resolved by the parties shall, upon thirty (30) days'
written notice by either party, be settled upon application of any such party by
arbitration in the County of Suffolk, Massachusetts, in accordance with the
prevailing National Rules for the Resolution of Employment Disputes of the
American Arbitration Association (AAA), and judgment upon the award rendered by
the arbitrator may be entered in any court of competent jurisdiction. The
arbitration filing fee shall be advanced by the initiating party and all other
AAA administrative fees under this Paragraph shall be shared equally by the
parties to such a dispute, subject to apportionment by the arbitrator in the
award.

                  6.5 Independent Advice. Executive acknowledges that Executive
has had the opportunity to evaluate this Agreement independently and with
Executive's own professional advisors, and has not received and is not relying
upon legal, tax or other professional advice from or on behalf of the Company in
connection with entering into this Agreement.

                  6.6 Section Headings. All section headings are included herein
for convenience and are not intended to affect in any way the meaning or
interpretation of this Agreement.

                  6.7 Severability. In the event any provision of this Agreement
is found to be invalid or unenforceable, such provision shall be severable from
the Agreement and shall not affect the validity or enforceability of any other
provision of this Agreement, which shall remain in full force and effect.

                  6.8 Entire Agreement. This Agreement constitutes the entire
agreement between the parties as to employment by the Company of Executive and
may only be changed by a written document signed by both parties. No agreements
or representations, oral or otherwise, express or implied, with respect to the
subject matter hereof have been made by either party which are not set forth
expressly in this Agreement.

                                       2
<PAGE>

                  6.9 Prior Agreements. This Agreement revokes, replaces and
supersedes any prior agreements and understandings, whether written or oral
relating to the subject matter of this Agreement between the Company and
Executive.

         IN WITNESS WHEREOF, the parties have executed this Agreement under seal
as of the date set forth above, the Company acting herein by its duly authorized
officer.

                                   I-MANY, INC.

                                   By:    /s/  WILLIAM F. DOYLE
                                          ----------------------
                                   Name:  William F. Doyle
                                   Title: Chairman of the Board
                                   Date:  October 17, 2001


                                   EXECUTIVE:

                                   By:     /s/ A. LEIGH POWELL
                                          ----------------------
                                   Name:   A. Leigh Powell
                                   Title:  Chief Executive Officer
                                   Date:   October 13, 2001


                                     6
<PAGE>

                        EXHIBIT A TO EMPLOYMENT AGREEMENT

               POSITION DESCRIPTION, SALARY AND BONUS INFORMATION



         The following provisions referenced in Sections 1 and 2 of the
Agreement shall govern the employment of Leigh Powell by the Company:

         1. PRIMARY RESPONSIBILITIES AND GOALS. Chief Executive Officer

         2. BASE SALARY. Base Salary shall be defined as $250,000.00 per year
(effective August 1, 2000) to be paid in accordance with regular payroll
practices.

         3. PREVIOUS BASE SALARY. Executive acknowledges full satisfaction of
any and all compensation due for services rendered to the Company prior to
the date hereof.


<PAGE>

                        EXHIBIT B TO EMPLOYMENT AGREEMENT

                                  BONUS PROGRAM

         Under the Company's discretionary, performance-based bonus program for
fiscal year 2000, Executive may earn a bonus in the amount equal to (a) a
minimum of 100%; and (b) a maximum of 300%, of Executives' base salary in effect
in fiscal year 2000, based on criteria to be established by the Company's Board
of Directors.


<PAGE>

                        EXHIBIT C TO EMPLOYMENT AGREEMENT

   [See attached forms of Demand Note, Pledge Agreement and Stock Assignment]

<PAGE>
                                   DEMAND NOTE

$_____________                                            As of ________, 2000

         FOR VALUE RECEIVED, A. Leigh Powell (the "Borrower"), at
______________________ ___________________, promises to pay to the order of
I-many, Inc. (the "Lender"), at 537 Congress Street, 5th Floor, Portland, ME
04101-3353, or at such other place as the Lender may designate, the principal
amount of _________________________ Dollars ($_________), together with interest
thereon, as set forth below.

         Interest (computed on the basis of the actual number of days elapsed
over a 365 day year) on the unpaid principal balance hereof, in each case
calculated from the date herein, shall accrue at a rate of Six and Thirty-three
Hundredths percent (6.33%) per annum.

         At any time and from time to time, the Lender, at its option, may
demand full repayment of all or any part of the unpaid principal and accrued
interest hereunder. In addition, this Note shall automatically become due and
payable in full upon the termination of the Borrower's employment with the
Lender, regardless of the reason for such termination.

         This Note applies, inures to the benefit of, and binds the successors
and assigns of the parties hereto. If any provision of this Note shall be
declared void or unenforceable by any judicial or administrative authority, the
validity of any other provision of this Note shall not be affected thereby. The
Borrower and each endorser or guarantor of this Note hereby waives presentment,
protest and all other demands and notices in connection with the delivery,
acceptance, performance, default or enforcement hereof, and agrees to pay all
costs of collection, including reasonable attorneys' fees and disbursements, in
case the principal of this Note, or any part thereof, or any interest thereon,
is not paid as demanded, or when due, whether suit be brought or not. No delay,
omission or forbearance on the part of the holder in exercising any right
hereunder, nor any waiver of any such right on any occasion, shall be construed
as a bar to or waiver of any such right on any future occasion.

         This Note evidences a certain loan from Lender to Borrower for the sole
purpose of the Borrower purchasing _______ shares of common stock of the Lender
and paying associated taxes as described in that certain Employment Agreement
dated as of ________, 2000, between Borrower and Lender (the "Agreement"), and
the holder hereof is entitled to the benefits of the Agreement. The payment and
performance of the obligations evidenced by this Note are secured by certain
collateral pursuant to a Pledge Agreement dated as of ________, 2000 between
Borrower and Lender (the "Pledge Agreement"). Neither this reference to such
Agreement and collateral nor any provision of Agreement or the Pledge Agreement
described in and contemplated by the Agreement shall affect or impair the
absolute and unconditional obligation of the Borrower to pay the principal of
and interest on this Note as provided herein.

         This Note shall be governed by and construed in accordance with the
laws of the Commonwealth of Massachusetts, excluding its conflicts of laws and
choice of laws provisions.

         EXECUTED AS AN INSTRUMENT UNDER SEAL as of the date first above
written.


                                               -----------------------------
                                                     A. Leigh Powell

<PAGE>

                                PLEDGE AGREEMENT

                             As of __________, 200__

        The undersigned (the "Obligor") has delivered to I-many, Inc. ("I-many")
certificate(s), duly endorsed in blank, evidencing the securities identified on
SCHEDULE A hereto, as the same may from time to time hereafter be amended, all
of which securities are (or will be) owned of record and beneficially by the
Obligor (sometimes referred to in this Agreement as the "Securities" or the
"collateral", which terms shall include any shares or other securities issued in
connection with any stock split, stock dividend, stock combination,
reorganization or similar event occurring with respect to the securities
identified on SCHEDULE A); and I-many has taken possession of such Securities
subject to such restrictions on transfer that may apply. The Obligor hereby
agrees that such collateral is to be held by I-many together with the proceeds
thereof (provided, that until the occurrence of a default on any of the
obligations secured hereunder, cash dividends paid upon or with respect to the
collateral shall be applied to pay the Note, as such term is defined below, in
accordance with the terms thereof respecting prepayments) as security for the
payment and performance of any and all obligations and liabilities of the
Obligor pursuant to that certain Demand Note in the principal amount of
$___________ dated as of _________, 200__, made by Obligor and payable to I-many
(the "Note").

        I-many may at any time demand, sue for, receive and collect any moneys
or money damages which may be or become payable under or on account of any
securities or any other property held as collateral hereunder. I-many may pay
such charges, taxes, assessments, liens and other expenses as it deems necessary
or convenient to protect, maintain, preserve or collect the collateral or any
part of it, or the value thereof, or any right pertaining thereto and, at any
time after a failure to perform under, or breach of, terms of the Note by the
Obligor ("Event of Default"), I-many may have the collateral transferred into
its own name or that of a nominee. Beyond the exercise of reasonable care to
assure the safe custody of securities or chattel paper while held hereunder
I-many shall be under no duty or liability to collect the collateral or the
income thereon or to protect or preserve rights pertaining thereto, and shall be
relieved of all responsibility for the collateral on surrendering it to the
Obligor.

        Upon the occurrence and during the continuance of an Event of Default
under the Note, I-many shall have all of the rights and remedies of a secured
party afforded by the Uniform Commercial Code as then in effect in Massachusetts
or afforded by other applicable law.

        I-many will give the Obligor not less than fifteen business days' notice
in writing, mailed, postage prepaid, to the last address of the Obligor known to
him, of the time and place of any sale of the collateral or after which any
private sale or intended disposition is to be made, which notice shall be deemed
reasonable. The Obligor agrees to pay upon default of any of the obligations
evidenced by the Note and secured hereunder all costs of collection, including
costs incurred in the sale or disposition of the collateral and reasonable fees
of an attorney, unless the Obligor can prove in legal proceedings that any such
default was declared by I-many in violation of the terms of this or any related
transaction document.

         No delay or omission on the part of I-many in exercising any right or
remedy shall operate as a waiver thereof or of any other right or remedy. Waiver
on any one occasion shall not be construed as a bar to or waiver of any right or
remedy on any future occasion. All of I-many's rights and remedies, whether
evidenced hereby or by any other agreement, instrument or paper, shall be
cumulative and may be exercised singularly or concurrently, and nothing herein
shall be deemed to limit in any way any rights I-many might otherwise have under
any other instrument or by law, including without limiting the generality
thereof, the right to negotiate the Note or any other instrument together with
any collateral specifically described therein.

<PAGE>

        Notwithstanding any other provision herein to the contrary, upon the
satisfaction of the obligations evidenced by the Note from the net proceeds of
the sale of the collateral, any excess proceeds shall be paid over to the
undersigned.

        If the Obligor identifies a purchaser for and desires to sell any of the
collateral, he shall make written request for the consent of I-many to release
such collateral from this Pledge for the purpose of effecting such sale, such
consent not to be unreasonably withheld or delayed; provided, however, that
I-many may condition consent to the release of such collateral upon the
prepayment of the Note by an amount equal to 100% of the net proceeds from the
sale of such collateral.

        This Agreement shall take effect as a sealed instrument and shall be
governed by and construed in accordance with the laws of the Commonwealth of
Massachusetts.

                               -----------------------------
                                 A. Leigh Powell

Agreed and Accepted:

I-MANY, INC.


By:
    ----------------------------
Name:
Title:





<PAGE>


                                   SCHEDULE A

_________ (___) Shares of the Common Stock of I-many, Inc., represented by
Certificate No. __.

<PAGE>

                              ASSIGNMENT OF SHARES


         FOR DUE CONSIDERATION, the undersigned hereby gifts, assigns and
transfers unto I-many, Inc., _________________ (__________) shares of common
stock, $.0001 per share par value (the "Shares"), of I-many, Inc. (the
"Company") standing in his name on the books of the Company, and does hereby
irrevocably appoint the Company as attorney to transfer said Shares on its
books, with full power of substitution in the premises.





Dated as of
             ------------------------                --------------------------
                                                     A. Leigh Powell


<PAGE>

                        EXHIBIT D TO EMPLOYMENT AGREEMENT

   [See attached Waiver and Amendment No.1 to Incentive Stock Option Agreements]


<PAGE>



                                     WAIVER


       Reference is hereby made to a certain Employment Agreement (the
"Employment Agreement") executed by A. Leigh Powell (the "Executive") and
I-many, Inc., a Delaware corporation (the "Company"), dated October 13, 2000
(the "Effective Date"), pursuant to which the Executive agreed to, among other
things, execute and deliver to the Company an Omnibus Amendment No.1 to
Incentive Stock Option Agreement (the "ISO Amendment"), a copy of which form was
attached to the Employment Agreement.

       Whereas, the ISO Amendment has not been fully executed by and between the
Executive and the Company, and both parties have agreed that it is in the best
interest of both parties not to enter into the ISO Amendment.

       Therefore, the Company hereby waives any and all rights to have the ISO
Amendment executed by the Executive, and the Company and the Executive hereby
consent to and confirm the effectiveness of the Employment Agreement as of the
Effective Date notwithstanding the fact that the ISO Amendment has not been, and
will not be, executed and entered into.

       IN WITNESS WHEREOF, the undersigned has duly executed this Waiver as an
instrument under seal.


Date: May 14, 2001                       I-MANY, INC.


                                         By: /s/ PHILIP M. ST. GERMAIN
                                            -----------------------------------
                                            Name:  Philip M. St. Germain
                                            Title: Chief Financial Officer




Date: May 14, 2001                       EXECUTIVE:

                                         By: /s/ A. LEIGH POWELL
                                            -----------------------------------
                                            A. Leigh Powell

<PAGE>


                                 AMENDMENT NO. 1
                                       TO
                        INCENTIVE STOCK OPTION AGREEMENTS


This Agreement is entered into by A. Leigh Powell (the "Executive") and I-many,
Inc., a Delaware corporation (the "Company") on May 14, 2001.

BACKGROUND: The Executive and the Company have entered into five stock options
agreements, with dates of April 29, 1998, May 3, 1999, July 27, 1999, September
23, 1999 and January 14, 2000 (each an "Option Agreement" and collectively, the
"Option Agreements"). On or about October 13, 2000, the Company and the
Executive verbally agreed to an amendment of the Option Agreements providing for
100% accelerated vesting upon a merger, change of control or sale the business
or assets of the Company. The parties are entering into this Agreement to
memorialize and ratify such amendment.

ACCORDINGLY, for good and valuable consideration, the receipt and sufficiency of
which is acknowledged, the parties agree as follows:

       1. Effective as of October 13, 2000, Section 3 of each Option Agreement
is amended by inserting at the end of Section 3 the following new paragraph:

            "(g) COMPANY SALE. Notwithstanding anything to the contrary
contained in Section 3: (i) if the Company is consolidated with or merged into
another entity (other than a consolidation or merger in which the stockholders
of the Company immediately prior to the consolidation or merger own a majority
of the issued and outstanding shares of stock of the survivor corporation (or of
an entity owning the survivor corporation) immediately after the consolidation
or merger); or (ii) if the business of the Company is acquired by another entity
in an acquisition of all or substantially all of the Company's assets; or (iii)
an entity acquiring in a transaction or series of related transactions in a
three-month period from the then-existing stockholders, more than 50% of the
Company's issued and outstanding shares of capital stock (each a "Company
Sale"); then all of the unvested shares on the date of the Company Sale shall
become exercisable in full immediately prior to the closing of such Company
Sale."

       2. Except as hereinabove set forth, each Option Agreement is confirmed
and ratified, and shall continue in full force and effect in accordance with its
terms, as amended.

       3. The Employee acknowledges and affirms that the Employee has had the
opportunity to consult with the Employee's own legal, tax and financial advisors
with respect to this Amendment and that he understands and agrees to the
consequences of this Amendment. The Employee hereby releases the Company, its
agents, officers, directors and employees from any and all claims or demands of
any kind and nature which the Employee now has or has ever had relating in any
way to an Option grant, an Option Agreement, this agreement, and any and all
actions taken in connection with or related to any of the foregoing.

       IN WITNESS WHEREOF, the parties have executed this Amendment under seal
as of the date first set forth above.

                                         I-MANY, INC.:

                                         By: /s/ PHILIP M. ST. GERMAIN
                                            -----------------------------------
                                            Name:   Philip M. St. Germain
                                            Title:  Chief Financial Officer

                                         EXECUTIVE:

                                         By: /s/ A. LEIGH POWELL
                                            -----------------------------------
                                            Name:    A. Leigh Powell

<PAGE>


                        EXHIBIT E TO EMPLOYMENT AGREEMENT

                            NONDISCLOSURE, INVENTION
                          AND NONCOMPETITION AGREEMENT

         In consideration of employment of the Employee by the Company and
payment to the Employee of salary or wages, this Agreement is made between
I-Many, Inc. (the "Company"), a Delaware corporation with a principal office at
537 Congress Street, 5th Floor, Portland, ME 04101-3353, and A. Leigh Powell
(the "Employee").

         1. BEST EFFORTS. The Employee agrees that, during the term of his
employment with the Company, he will serve the Company faithfully and to the
best of his ability and will devote his full business and professional time,
energy and diligence to the business and affairs of the Company and to the
performance of his duties as reasonably directed by the President of the Company
or anyone designated by him.

         2. CONFIDENTIAL INFORMATION. The Employee acknowledges that, in order
for him to perform his duties properly, the Company must necessarily entrust the
Employee with certain trade secrets and confidential business information (the
"Confidential Information"). The Confidential Information includes, but is not
limited to: source code, object code, operational and functional features and
limitations of the Company's software; the Company's research and development
plans and activities; the Company's manufacturing and production plans and
activities; the prices, terms and conditions of the Company's contracts with its
customers; the identities, needs and requirements of the Company's customers;
the Company's pricing policies and price lists; the Company's business plans and
strategies; the Company's marketing plans and strategies; personnel information;
and financial information regarding the Company. The Employee further
acknowledges that the development or acquisition of such Confidential
Information is the result of great effort and expense by the Company, that the
Confidential Information is critical to the survival and success of the Company,
and that the unauthorized disclosure or use of the Confidential Information
would cause the Company irreparable harm.

          3. NONDISCLOSURE OF CONFIDENTIAL INFORMATION. The Employee agrees
that, during the term of his employment with the Company and thereafter, he will
not disclose the Confidential Information or use it in any way, except on behalf
of the Company, whether or not such Confidential Information is produced by the
Employee's own efforts. The Employee further agrees, upon termination of his
employment, promptly to deliver to the Company all Confidential Information,
whether or not such Confidential Information was produced by the Employee's own
efforts, and to refrain from making, retaining or distributing copies thereof.

         4. INVENTIONS AND DISCOVERIES. Any invention, discovery, development,
improvement, procedure, writing, work or trade secret (collectively referred to
herein as "Inventions") that relates to any phase of the business of the
Company, or results from any work performed on the premises of the Company or by
use of the facilities, equipment or services of other employees of the Company,
whether patentable, copyrightable or not, and that is made or discovered by the
Employee individually or jointly with any other person or persons during the
term of the Employee's employment with the Company, shall forthwith be disclosed
to the Company and shall be the sole property of the Company. Any such Invention
shall be considered a work made for hire. The Employee assigns to the Company
all of his right, title and interest to any such

                                                                             2
<PAGE>

Invention. The Employee further agrees to maintain adequate, current written
records of any Invention within the scope of the foregoing provisions in the
form of notes, sketches, drawings, memoranda or other written evidence, which
records shall be and remain the sole property of the Company.

         5. PATENTS, TRADEMARKS AND COPYRIGHTS. The Employee agrees that, during
the term of his employment with the Company and thereafter, he will, whenever
requested to do so by the Company and at the expense of the Company, apply or
join with the Company in applying for patents, trademarks, copyrights, letters
patent and other means for the protection of proprietary information, both
foreign and domestic, with respect to any Invention described in paragraph 4.
The Employee shall execute and deliver to the Company any and all other
documents and instruments that, in the opinion of the Company and its counsel,
are appropriate in order to obtain said patents, trademarks, copyrights, letters
patent and other means of protecting proprietary information. The Employee shall
further execute and deliver all such other instruments and take all other
actions that in the opinion of the Company and its counsel shall be appropriate
to vest in the Company (or in such person as the Company may specify) all right,
title and interest in said patents, trademarks, copyrights, letters patent and
other means of protecting proprietary information, and shall cooperate and
assist in any litigation commenced by the Company against third parties with
respect to the same.

         6. POWER OF ATTORNEY. In the event the Company is unable, after
reasonable effort, to secure Employee's signature on any letters patent,
copyright or other analogous protection relating to an Invention, whether
because of Employee's physical or mental incapacity or for any other reason
whatsoever, Employee irrevocably designates and appoints the Company and its
duly authorized officers and agents as his agent and attorney-in-fact, to act
for and in his behalf and stead to execute and file any such application or
applications and to do all other lawfully permitted acts to further the
prosecution thereon with the same legal force and effect as if executed by
Employee.

         7. EMPLOYEE DEVELOPMENTS. Employee represents that all inventions,
discoveries, developments, improvements, procedures, writings, works, trade
secrets or other intellectual property rights to which Employee claims ownership
as of the date of this Agreement (the "Employee Developments"), and which the
parties agree are excluded from this Agreement, are listed in Exhibit A attached
hereto. If no such Employee Developments are listed in Exhibit A, Employee
represents that there are no such Employee Developments at the time of signing
this Agreement.

         8.       RESTRICTIONS ON COMPETITION.

         The Employee agrees that, during the term of his employment with the
Company and for a period of one (1) year after termination for any reason of
Employee's employment, he will not, directly or indirectly, render services to,
work for or on behalf of, have an interest in, make any loan to, or assist in
any manner any business in ____________________ that is competitive with that in
which the Company was engaged or planned to engage on the date of the Employee's
termination from the Company. The foregoing shall not prevent the Employee from
owning up to one percent (1%) of the outstanding securities of a publicly held
corporation that may compete with the Company.

         The Employee agrees that, during the term of his employment with the
Company and for a period of one (1) year after termination for any reason of
Employee's employment, he will not, directly or indirectly, solicit or accept
work from any

                                                                             3
<PAGE>

individual or entity that was a customer of the Employer during the
Employee's employment with the Company.

         The Employee further agrees that, during the term of his employment
with the Company and for a period of one (1) year after termination for any
reason of Employee's employment, he will not, directly or indirectly, render
services to or work for or on behalf of any individual or entity that was a
customer of the Company during the Employee's employment with the Company.

         9. NOTICE OF SUBSEQUENT EMPLOYMENT. Employee shall, for a period of one
(1) year after the termination of employment with the Company, notify the
Company of any change of address, and of any subsequent employment (stating the
name and address of the employer and the title and duties of the position) or
other business activity.

         The Employee further agrees that the Company may, following termination
of the Employee's employment for a period of one (1) year, communicate with the
Employee's new employer for the purpose of informing the new employer of the
existence of this Agreement and providing the new employer with a copy of this
Agreement.

         10. ENTICEMENT. For a period of one (1) year after the termination of
employment with the Company, Employee will not hire or attempt to hire any
employee of the Company, or assist in such hiring by anyone else, to work as an
employee or independent contractor with any business that is competitive with
that in which the Company was engaged or planned to engage on the date of the
Employee's termination from the Company.

         11. RETURN OF COMPANY PROPERTY. The Employee agrees, upon termination
of his employment, promptly to deliver to the Company all files, keys, building
passes, credit cards, books, documents, computer disks or tapes, and other
property prepared by or on behalf of the Company or purchased with Company
funds, and to refrain from making, retaining or distributing copies thereof. To
the extent that Employee has any data belonging to the Company on any
non-removable magnetic media owned by Employee (for example, a computer's hard
disk drive), Employee agrees that immediately upon termination s/he will provide
the Company with a copy of the data and then purge his or her computer of the
data.

         12. SPECIFIC PERFORMANCE. The Employee acknowledges that a breach of
this Agreement by the Employee will cause irreparable injury to the Company,
that the Company's remedies at law will be inadequate in case of any such
breach, and that the Company will be entitled to preliminary injunctive relief
and other injunctive relief in case of any such breach.

         13. COMPLIANCE WITH OTHER AGREEMENTS. The Employee represents and
warrants to the Company that the execution of this Agreement by him, his
performance of his obligations hereunder, and his employment by the Company will
not, with or without the giving of notice or the passage of time, conflict with,
result in the breach or termination of, or constitute default under, any
agreement to which the Employee is a party or by which the Employee is or may be
bound.

         14. EMPLOYMENT AT WILL. The Employee agrees that he is an at-will
employee of the Company and that he may terminate his employment at any time.
The Employee further agrees that the Company may similarly terminate the
Employee's employment at any time. This Agreement does not create an obligation
on the part of the Company or any other person to continue the employment of the
Employee.

                                                                             4
<PAGE>

         15. WAIVERS. The waiver by the Company or the Employee of any action,
right or condition in this Agreement, or of any breach of a provision of this
Agreement, shall not constitute a waiver of any other occurrences of the same
event.

         16. SURVIVAL; BINDING EFFECT. This Agreement shall survive the
termination of the Employee's employment with the Company regardless of the
manner of such termination, and shall be binding upon the Employee and his
heirs, executors and administrators.

         17. ASSIGNABILITY BY COMPANY. This Agreement is assignable by the
Company and inures to the benefit of the Company, its subsidiaries, affiliated
corporations, successors and assignees. This Agreement, being personal, is not
assignable by the Employee.

         18. HEADINGS; GENDER REFERENCES. The section headings in this Agreement
are for reference purposes only and shall not be deemed to be a part of this
Agreement or to affect the meaning or interpretation of this Agreement. Wherever
used herein, the masculine pronoun shall, as appropriate, be construed to
include the feminine.

         19. SEVERABILITY. The covenants of this Agreement are intended to be
separable, and the expressions used therein are intended to refer to divisible
entities. Accordingly, the invalidity of all or any part of any paragraph of
this Agreement shall not render invalid the remainder of this Agreement or of
such paragraph. If, in any judicial proceeding, any provision of this Agreement
is found to be so broad as to be unenforceable, it is agreed that such provision
shall be interpreted to be only so broad as to be enforceable.

         20. GOVERNING LAW. This Agreement shall be deemed to have been made in
Massachusetts and shall be governed by and construed in accordance with the
substantive law of Massachusetts, excluding, however, such laws as pertain to
conflicts of law.

         21. CONSENT TO JURISDICTION. Employee consents and submits to the
jurisdiction of the state and federal courts in the state in which the Company's
principal place of business is located at the time of termination of Employee's
employment.

         22. ATTORNEY'S FEES. Employee agrees that in the event that the
Employer brings suit to enforce any term of this Agreement, the Employee shall
be liable for the Employer's reasonable attorney's fees and costs with respect
to any claim or counterclaim as to which the Employer is the prevailing party.

         23. ENTIRE AGREEMENT; AMENDMENTS. This Agreement constitutes the entire
understanding of the parties with respect to its subject matter, supersedes any
prior communication or understanding with respect thereto, and no modification
or waiver of any provision hereof shall be valid unless made in writing and
signed by the parties.

         24. UNDERSTANDING OF AGREEMENT. THE EMPLOYEE STATES THAT HE HAS HAD A
REASONABLE PERIOD SUFFICIENT TO STUDY, UNDERSTAND AND CONSIDER THIS AGREEMENT,
THAT HE HAS HAD AN OPPORTUNITY TO CONSULT WITH COUNSEL OF HIS CHOICE, THAT HE
HAS READ THIS AGREEMENT AND UNDERSTANDS ALL OF ITS TERMS, THAT HE IS ENTERING
INTO AND SIGNING THIS AGREEMENT KNOWINGLY AND VOLUNTARILY, AND THAT IN DOING SO
HE IS NOT RELYING UPON ANY STATEMENTS OR REPRESENTATIONS BY THE COMPANY OR ITS
AGENTS.

                                                                             5
<PAGE>

         IN WITNESS WHEREOF, the parties have duly executed this Agreement under
seal as of the 30th day of September 2000.

I-MANY, INC.


By:  /s/ Philip M. St. Germain                    /s/ A. Leigh Powell
     --------------------------------            -----------------------------
      Philip M. St. Germain                       A. Leigh Powell
      Chief Financial Officer                     744 Signal Light Road
                                                  Moorestown, New Jersey 08057



<PAGE>

                      EXHIBIT A TO NONDISCLOSURE, INVENTION
                          AND NONCOMPETITION AGREEMENT


                          List of Employee Developments