Document:

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                                                                   EXHIBIT 10.48

[CRITICAL PATH LOGO]

February 4, 2004

Mr. James Clark
3075 Welwyn Place
Walnut Creek, CA 94598

Dear Jim,

On behalf of Critical Path, Inc. (the "Company"), I am pleased to offer you the
position of Executive Vice President, Chief Financial Officer. Speaking for
myself, as well as other members of the Company's management team, we are all
very impressed with your credentials and we look forward to your future success
in this position.

The terms of your employment with the Company are set forth below:

POSITION          You will be an Executive Vice President, Chief Financial
                  Officer for the Company, reporting to William E. McGlashan,
                  Jr., Chief Executive Officer, working out of the Company's
                  offices in San Francisco, CA, or from your home office. This
                  is an exempt position.

                  You agree to the best of your ability and experience that you
                  will at all times loyally and conscientiously perform all of
                  the duties and obligations required of and from you pursuant
                  to the express and implicit terms hereof, and to the
                  reasonable satisfaction of the Company. During the term of
                  your employment, you further agree that you will devote all of
                  your business time and attention to the business of the
                  Company.

START DATE        Subject to fulfillment of any conditions imposed by this
                  letter agreement, you will commence this new position with the
                  Company on a date to be determined. Kim Trask of our Human
                  Resources Department will contact you regarding your new hire
                  orientation.

COMPENSATION      Your base salary will be $250,000.00 on an annualized basis.
                  Your salary will be payable in two equal payments per month
                  pursuant to the Company's regular payroll practices. Your base
                  salary will be increased to $300,000.00 once the Company is
                  EBITDA profitable.

BONUS             You will be eligible to participate in the 2004 Critical Path
                  Bonus Plan, once finalized and approved by our Board of
                  Directors, at 30% of base salary, on a prorated basis based on
                  your date of hire.

REVIEW            Your base salary will be reviewed annually as part of the
                  Company's salary review process. However, nothing in this
                  provision changes the at-will nature of the employment
                  relationship.

BENEFITS          The Company offers you and your eligible dependents generous
                  Medical, Dental, and Vision benefits. You will also receive
                  Short-term Disability, Long-term Disability, and Life
                  Insurance. In addition, the Company offers employees the
                  opportunity to participate in its Flexible Spending Account,
                  Employee Assistance Program, 401(k) Plan, and

                                                             Critical Path, Inc.

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                  Employee Stock Purchase Plan. A complete overview of benefits
                  will be presented to you on or around your date of hire.

PAID TIME OFF     Members of the executive staff are not eligible to accrue
                  Paid Time Off (PTO). You should schedule time off for the year
                  based on your tenure with the Company and the number of days
                  allowed per year according to our policy, a copy of which will
                  be given to you at orientation. If you should leave the
                  Company for any reason, you will not receive any PTO payout on
                  your final paycheck.

STOCK OPTIONS     In connection with the commencement of your employment, the
                  Company will recommend that the Board Compensation Committee
                  grant you an option to purchase 350,000 shares of the
                  Company's Common Stock ("Shares") with an exercise price equal
                  to the closing price of Critical Path's stock on the last
                  trading day prior to the date of Grant. These Shares will vest
                  over four years, with 12.5% vesting on your six-month
                  anniversary with the Company, and 1/48th of the original grant
                  amount vesting monthly thereafter. Vesting will, of course,
                  depend on your continued employment with the Company. These
                  Shares will be subject to the terms of the applicable Company
                  Stock Option Plan and the Stock Option Agreement between you
                  and the Company.

                  In the event of a Change of Control of the Company, any
                  unvested Shares originally granted will vest immediately
                  should your employment be terminated without Cause or if you
                  terminate your employment for Good Reason, each such event
                  occurring within six (6) months of such Change of Control, all
                  as such terms are defined in Appendix A.

SEVERANCE         To the extent you are terminated for any reason without Cause
                  (as defined on Appendix A), you will receive, upon
                  termination, a severance payment equal to six (6) months base
                  salary.

PROOF OF RIGHT TO WORK

                  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.
                  A list of acceptable documents is available for your
                  reference. Please have your identity and employment
                  eligibility document(s) with you for your new hire
                  orientation.

PROPRIETARY INFORMATION AND INVENTIONS AGREEMENT

                  Your acceptance of this offer and commencement of employment
                  with the Company is contingent upon the execution and
                  submission of the Company's Proprietary Information and
                  Inventions Agreement ("Proprietary Agreement"), a copy of
                  which has been provided to you with this offer letter.

AT-WILL EMPLOYMENT

                  Notwithstanding the Company's obligation described herein,
                  your employment with the Company will be on an "at-will"
                  basis, meaning that either you or the Company may terminate
                  your employment at any time for any reason or no reason,
                  without further obligation or liability.

DISPUTE RESOLUTION PROCEDURE

                  You and the Company ("the parties") agree that any dispute
                  arising out of or related to the employment relationship
                  between them, including the termination of that relationship
                  and any allegations of unfair or discriminatory treatment
                  arising under state or federal law or otherwise, that cannot
                  be resolved through the Company's informal grievance
                  procedure, shall be resolved by final and binding arbitration
                  in San Francisco, California, except where the law
                  specifically forbids the use of arbitration as a final and
                  binding remedy. The following dispute resolution shall apply:

                  (a) The complainant shall provide the other party with a
                      written statement of the claim identifying any supporting
                      witnesses or documents and the requested relief.

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                  (b) The respondent shall furnish a statement of the relief, if
                      any, that it is willing to provide, and identify
                      supporting witnesses or documents. If the matter is not
                      resolved, the parties shall submit the dispute to
                      nonbinding mediation, paid for by the Company, before a
                      mediator to be selected by the parties.

                  (c) If the matter is not resolved through mediation, the
                      parties agree that the dispute shall be resolved by
                      binding arbitration. If the parties are unable to jointly
                      select an arbitrator, they will obtain a list of
                      arbitrators in San Francisco County, California, from the
                      Federal Mediation and Conciliation Service and select an
                      arbitrator by striking names from that list.

                  (d) The arbitrator shall have the authority to determine
                      whether the conduct complained of in section (a) of this
                      section violates the complainant's rights and, if so, to
                      grant any relief authorized by law; subject to the
                      exclusions of section (g) below. The arbitrator shall not
                      have the authority to modify, change, or refuse to enforce
                      the terms of any employment agreement between the parties,
                      or change any lawful policy or benefit plan.

                  (e) The Company shall bear the costs of the arbitration if you
                      prevail. If the Company prevails, you will pay half the
                      cost of the arbitration or $500, whichever is less. Each
                      party shall pay its own attorney's fees, unless the
                      arbitrator orders otherwise pursuant to applicable law.

                  (f) ARBITRATION SHALL BE THE EXCLUSIVE FINAL REMEDY FOR ANY
                      DISPUTE BETWEEN THE PARTIES, SUCH AS DISPUTES INVOLVING
                      CLAIMS FOR DISCRIMINATION OR HARASSMENT (SUCH AS CLAIMS
                      UNDER THE FAIR EMPLOYMENT AND HOUSING ACT, TITLE VII OF
                      THE CIVIL RIGHTS ACT OF 1964, THE AMERICANS WITH
                      DISABILITIES ACT, OR THE AGE DISCRIMINATION IN EMPLOYMENT
                      ACT), WRONGFUL TERMINATION, BREACH OF CONTRACT, BREACH OF
                      PUBLIC POLICY, PHYSICAL OR MENTAL HARM OR DISTRESS, OR ANY
                      OTHER DISPUTES, AND THE PARTIES AGREE THAT NO DISPUTE
                      SHALL BE SUBMITTED TO ARBITRATION WHERE THE COMPLAINANT
                      HAS NOT COMPLIED WITH THE PRELIMINARY STEPS PROVIDED FOR
                      IN SECTIONS (A) AND (B) ABOVE.

                  (g) The parties agree that the arbitration award shall be
                      enforceable in any court having jurisdiction to enforce
                      this agreement, so long as the arbitrator's findings of
                      fact are supported by substantial evidence on the whole
                      and the arbitrator has not made errors of law; however,
                      either party may bring an action in a court of competent
                      jurisdiction regarding or related to inventions that you
                      may claim to have developed prior to joining the Company,
                      pursuant to California Labor Code Section 2870 ("Disputes
                      Related to Inventions"). The parties further agree that
                      for Disputes Related to Inventions which the parties have
                      elected to submit to arbitration, each party retains the
                      right to seek preliminary injunctive relief in court in
                      order to preserve the status quo or prevent irreparable
                      injury before the matter can be heard in arbitration.

OFFER CONDITIONS

                  This offer is null and void if not accepted or declined by
                  close of business on February 2, 2004. This offer is also
                  contingent upon receiving your completed employment
                  application and the successful results of our independent
                  verification of your application and reference checks.

We are delighted to be able to extend you this offer and look forward to working
with 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 Donna Spinola in
the Human Resources department (if by fax, then to 415.541.2301), along with a
signed and dated copy of the Proprietary Agreement. This letter, together with
the Proprietary Agreement, constitute the full, complete, and exclusive
agreement between you and the Company regarding the matters herein and
supersedes any prior representations or agreements, whether written or

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oral. This letter may not be modified or amended except by a written agreement,
signed by the Company and by you.

ACCEPTED AND AGREED:                    CRITICAL PATH, INC.

Name: James Clark                       By: /s/ William E. McGlashan, Jr.
                                           ------------------------------------
                                                 William E. McGlashan, Jr.
                                           Chairman and Chief Executive Officer

Signed: /s/ James Clark
       ---------------------------
Date: February 4, 2004

                                                             Critical Path, Inc.

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                                   APPENDIX A

"Change of Control" shall mean the consummation of one of the following: (i) the
acquisition of 50% or more of the outstanding stock of the Company pursuant to a
tender or exchange offer validly made under any federal or state law (other than
a tender offer by the Company) or other share acquisition transaction; (ii) a
merger, consolidation or other reorganization of the Company (other than a
reincorporation of the Company), if after giving effect to such merger,
consolidation or other reorganization of the Company, the shareholders of the
Company immediately prior to such merger, consolidation or other reorganization
do not represent a majority in interest of the holders of voting securities (on
a fully diluted basis) with the ordinary voting power to elect directors of the
surviving entity after such merger, consolidation or other reorganization; (iii)
the sale of all or substantially all of the assets of the Company to a third
party who is not an affiliate of the Company.

"Cause" shall mean (i) failure or refusal to perform a lawful directive of the
CEO or the Board of Directors of the Company that is consistent with your duties
and responsibilities as set forth in this Agreement, (ii) willful misconduct or
material violation of your fiduciary obligations to the Company , (iii) you
perform your duties in a grossly negligent manner, or (iv) you are convicted of
any crime that has a material adverse impact on (A) your ability to perform your
duties hereunder, (B) the Company or (C) the Company's business.

"Good Reason" shall be deemed to occur if there is (a)(1) a material adverse
change in your position causing such position to be of significantly less
stature or of significantly less responsibility, (2) a material adverse change
in title, (3) a material reduction of employee's base salary, or (4) a material
change in your bonus structure or bonus targets such that your total potential
compensation will necessarily be materially reduced; and (b) within the sixty
(60) day period immediately following any of the foregoing events employee
elects to terminate his employment voluntarily.

                                                             Critical Path, Inc.

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                                                                   EXHIBIT 10.51

                               FIRST AMENDMENT TO
                              AMENDED AND RESTATED
                           LOAN AND SECURITY AGREEMENT

         THIS FIRST AMENDMENT TO AMENDED AND RESTATED LOAN AND SECURITY
AGREEMENT (the "Amendment") is entered into as of November 26, 2003, by and
between SILICON VALLEY BANK, a California-chartered bank (the "Bank"), and
CRITICAL PATH, INC., a California corporation (the "Borrower"), in reliance on
the following:

                                    RECITALS

         A.       On or about July 18, 2003, the Borrower and the Bank entered
into that certain Amended and Restated Loan and Security Agreement pursuant to
which the Bank made available to the Borrower a revolving credit facility (the
"Senior Debt Facility") in the principal amount of up to Fifteen Million Dollars
($15,000,000.00). The Amended and Restated Loan and Security Agreement, along
with all other documents entered into by or on behalf of the Borrower in
connection therewith, are hereinafter referred to as the "Senior Loan
Documents", and each capitalized term used in this Amendment shall have the
meaning accorded to it in the Senior Loan Documents unless it is otherwise
defined herein.

         B.       The Borrower has entered into that certain Convertible Note
Purchase and Exchange Agreement, dated as of November 18, 2003, among the
Borrower, General Atlantic Partners 74, L.P. ("GAP 74"), GAP Coinvestment
Partners II, L.P. ("GAP Coinvestment"), GapStar, LLC ("GapStar") and GAPCO GmbH
& Co. KG ("GAPCO" and, together with GAP 74, GAP Coinvestment and GapStar, the
"Investors"), and the other entities listed on the signature pages thereto
(collectively with the notes and other documents to be executed and delivered by
the Borrower in connection therewith, as amended in accordance with the terms of
the Subordination Agreement defined below, the "Junior Debt Documents"),
pursuant to which the Borrower will issue to such Investors convertible notes in
the aggregate principal amount of Ten Million Dollars ($10,000,000) (the "Junior
Debt") and will grant to the Investors a security interest in certain of the
Collateral on November 26, 2003. The Bank is willing to consent to the
Borrower's entering into the Junior Debt Documents, issuing the convertible
notes thereunder to the Investors and granting a security interest in certain of
the Collateral to the Investors, but only upon the terms hereof.

                                    AGREEMENT

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

                  1        Consent to Junior Debt Documents. The Bank hereby
consents to each of the Borrower's and the Borrower's direct and indirect
subsidiaries' (including but not limited to its subsidiary Compass Holding
Corp.): (i) incurring indebtedness and guarantees of indebtedness under the
Junior Debt Documents; (ii) granting to the Investors a security interest in

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its assets and property, all as more fully set forth in the Junior Debt
Documents (it being acknowledged by the Bank that such security interest shall
constitute a "Permitted Lien" under the Senior Loan Documents to the extent that
such security interest is subordinate to the Bank's lien upon the Collateral as
provided in the Subordination Agreement); and (iii) entering into and performing
their obligations under the Junior Debt Documents; provided, however, that the
Bank's consent to the foregoing is expressly predicated upon the terms of the
Junior Debt Documents as of the date of this Amendment and does not constitute,
nor is it intended to constitute, a consent to any subsequent modifications to
the Junior Debt Documents. The Bank also hereby consents to the changes in the
Borrower's capital structure, the conversion of all or any portion of the Junior
Debt into equity interests of the Borrower or another entity (as contemplated by
the convertible notes referred to above) at any time and the consummation of all
other transactions contemplated by the Junior Debt Documents pursuant to their
respective terms as of the date hereof.

                  2        No Amendment of Junior Debt Documents. The Borrower
agrees that it shall not enter into, nor consent to, any amendment of the Junior
Debt Documents that is likely to result in a material adverse change to the
Bank's rights and remedies under the Senior Debt Documents or the Subordination
Agreement without first obtaining the Bank's consent thereto.

                  3        Reduction of the Credit Limit. On and after the
effective date of this Amendment, the Bank shall reduce the Credit Limit from
Fifteen Million Dollars ($15,000,000.00) to Five Million Dollars ($5,000,000.00)
(the "New Credit Limit") and shall also reduce the Letter of Credit Sublimit
from Six Million Dollars ($6,000,000.00) to Two Million Eight Hundred Thousand
Dollars ($2,800,000.00).

                  4        Reaffirmation of Obligations. The Borrower reaffirms
to the Bank that, as of the date hereof, the outstanding principal amount of all
Loans under the Senior Loan Documents (including the face amount of all Letters
of Credit outstanding under the Letter of Credit Sublimit) is Seven Million Four
Hundred Thousand and No/100 Dollars ($7,400,000.00). The Borrower acknowledges
that the Senior Loan Documents fully and accurately reflect and constitute the
valid and enforceable Obligations of the Borrower to the Bank, and the Borrower
remains fully obligated to perform all covenants thereunder and has no defenses
to or offsets against such Obligations.

                  5        Conditions to Effectiveness. The following conditions
must be satisfied in full, or waived in writing by the Bank, before this
Amendment shall be effective and the Bank shall become obligated hereunder.

                           5.1      Execution and Delivery of Documents. The
Borrower shall have executed and delivered to the Bank this Amendment, and the
Bank shall have received any and all other instruments and documents, fully
executed and in form and substance acceptable to the Bank, as are contemplated
hereby or otherwise reasonably requested by the Bank, including the
Subordination Agreement with the Investors.

                           5.2      Payment of Fees and Expenses. The Borrower
shall have paid to the Bank all fees due and owing under the Senior Loan
Documents as amended hereby, as well as a sum sufficient to reimburse the Bank
for all costs and expenses incurred by the Bank in

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entering into this Amendment, the Subordination Agreement and any and all other
documents and instruments contemplated hereby or thereby (including but not
limited to all attorneys' fees and expenses.)

                           5.3      Payment of Principal Accrued Interest. The
Borrower shall have paid to the Bank all outstanding principal amounts under the
Senior Loan Documents in excess of the New Credit Limit, plus all accrued
interest thereon that is due and owing, on or before the date on which this
Amendment becomes effective.

                           5.4      Representations and Warranties; No Default.
The representations and warranties of the Borrower as set forth in the Senior
Loan Documents shall be true and correct in all material respects as of the date
on which this Amendment becomes effective, and no Event of Default shall have
occurred and be continuing as of such date without having been cured.

                  6        Continued Full Force and Effect. Except to the extent
expressly amended hereby, all of the terms and provisions of the Senior Loan
Documents shall remain in full force and effect, and the lien in favor of the
Bank in the Collateral shall be and remain a fully perfected senior lien upon
all of the Collateral pursuant to the terms of the Senior Loan Documents, it
being the intent of the parties that nothing herein shall affect or impair the
Bank's rights or remedies under the Senior Loan Documents or its lien upon the
Collateral. Henceforth, the term "Loan Documents" shall be deemed to mean the
Senior Loan Documents as modified and supplemented by the terms of this
Amendment, and any default of the Borrower hereunder shall constitute an Event
of Default under the Senior Loan Documents.

                  7        General Provisions.

                           7.1      Choice of Law and Venue. This Amendment
shall be governed by and construed in accordance with the internal laws of the
State of California, without regard to principles of conflicts of law, and any
action or proceeding arising out of this Agreement shall be commenced in the
Superior Court of the State of California for the County of Santa Clara, or in
the District Court of the United States in the Northern District of California.

                           7.2      WAIVER OF JURY TRIAL. EACH OF THE BORROWER,
ON THE ONE HAND, AND THE BANK, ON THE OTHER HAND, WAIVES ITS RIGHT TO A JURY
TRIAL OF ANY CLAIM OR CAUSE OF ACTION ARISING OUT OF OR BASED UPON THIS
AMENDMENT, THE LOAN AGREEMENT OR ANY CONTEMPLATED TRANSACTION, INCLUDING
CONTRACT, TORT, BREACH OF DUTY AND ALL OTHER CLAIMS. THIS WAIVER IS A MATERIAL
INDUCEMENT FOR EACH OF THE PARTIES TO ENTER INTO THIS AMENDMENT. EACH PARTY HAS
REVIEWED THIS WAIVER WITH ITS COUNSEL AND UNDERSTANDS THE RAMIFICATIONS THEREOF.

                           7.3      Entire Agreement. This Amendment and the
Loan Agreement together constitute the entire agreement and understanding
between the parties hereto with respect to the transactions contemplated
hereunder and thereunder and supersede all prior

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negotiations, understandings and agreements between the parties with respect to
such transactions.

                           7.4      Counterparts. This Amendment may be executed
and delivered in any number of counterparts, each of which shall be an original
and all of which together shall constitute one and the same agreement.

                           7.5      Time of the Essence. Time is of the essence
in the performance by each party of its obligations hereunder and the
satisfaction of all conditions specified herein.

         IN WITNESS WHEREOF, each of the parties hereto has caused its duly
authorized representative to execute this Amendment as of the date first set
forth above.

BORROWER:                                    BANK:

CRITICAL PATH, INC.                          SILICON VALLEY BANK,
a California corporation                     a California-chartered bank

CRITICAL PATH, INC.                          SILICON VALLEY BANK,
a California corporation                     a California-chartered bank

By: /s/ Michael J. Zukerman                  By: /s/ Brian Harrison
   --------------------------------             -----------------------------
Name:  Michael J. Zukerman                   Name:  Brian Harrison
Title: SVP and General Counsel               Title: Vice President

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