<PAGE>
                                                                   EXHIBIT 10.10

                       FOURTH LOAN MODIFICATION AGREEMENT

         THIS FOURTH LOAN MODIFICATION AGREEMENT (this "Agreement") is entered
into as of April 29, 2003 by and between SILICON VALLEY BANK ("Bank"), whose
address is 3003 Tasman Drive, Santa Clara, California 95054 and having a loan
production office at One North Clematis Street, Suite 510, West Palm Beach,
Florida 33401 and THE ULTIMATE SOFTWARE GROUP, INC., a corporation organized and
in good standing in the State of Delaware ("Borrower"), whose address is 2000
Ultimate Way, Weston, Florida 33326.

1. DESCRIPTION OF EXISTING OBLIGATIONS: Among other Obligations which may be
owing by Borrower to Lender, Borrower is indebted to Lender pursuant to, among
other documents, a Loan and Security Agreement, dated November 29, 2001 (as may
be amended from time to time, the "Loan Agreement"). The Loan Agreement provides
for, among other things, a Committed Revolving Line, with a sublimit for
Equipment Advances (the "Equipment Advance Sublimit"). Hereinafter, all
obligations owing by Borrower to Lender shall be referred to as the
"Obligations."

2. DESCRIPTION OF COLLATERAL. Repayment of the Obligations is secured by the
Collateral as described in the Loan Agreement. Hereinafter, the Loan Agreement,
together with all other documents evidencing or securing the Obligations shall
be referred to as the "Existing Loan Documents".

3. DESCRIPTION OF CHANGE IN TERMS. Borrower is in violation of Section 6.7(i) of
the Loan Agreement for the month ending March 31, 2003 and has requested that
Lender waive this violation. Accordingly, Lender hereby agrees to waive
compliance with Section 6.7(i) for the period ending March 31, 2003 and Borrower
and Lender further agree that effective as of the date hereof, Section 6.7(i) of
the Loan Agreement is amended and restated in its entirety as follows:

         (i) QUICK RATIO. A ratio of Quick Assets to Current Liabilities of at
         least 1.75 to 1.00.

4. COMPLIANCE CERTIFICATE. EXHIBIT C (Compliance Certificate) to the Loan
Agreement is replaced in its entirety with EXHIBIT C attached hereto.

5. CONSISTENT CHANGES. The Existing Loan Documents are hereby amended wherever
necessary to reflect the changes described above.

6. PAYMENT OF LOAN FEE. In consideration of Lender's agreement to enter into
this Agreement, the Borrower shall pay to Lender on the date hereof a loan fee
in the amount of Two Thousand Dollars ($2,000) (the "Loan Fee") plus all
out-of-pocket expenses, including, without limitation, Lender's attorneys' fees.
The Loan Fee is considered earned when paid and is not refundable.

7. NO DEFENSES OF BORROWER. Borrower agrees that it has no defenses against the
obligations to pay any amounts under the Obligations.

8. CONTINUING VALIDITY. Borrower understands and agrees that in modifying the
existing Obligations, Lender is relying upon Borrower's representations,
warranties, and agreements, as set forth in the Existing Loan Documents. Except
as expressly modified pursuant to this Agreement, the terms of the Existing Loan
Documents remain unchanged and in full force and effect. Lender's agreement to
modifications to the existing Obligations pursuant to this Agreement in no way
shall obligate Lender to make any future modifications to the Obligations.
Nothing in this Agreement shall constitute a satisfaction of the Obligations. It
is the intention of Lender and Borrower to retain as liable parties all makers
and endorsers of Existing Loan Documents, unless the party is expressly released
by Lender in writing. No maker, endorser, or guarantor will be released by
virtue of this Agreement. The terms of this paragraph apply not only to this
Agreement, but also to all subsequent loan modification agreements.

9. CONDITIONS. The effectiveness of this Agreement is conditioned upon
Borrower's payment of the Loan Fee and all fees required under Section 6 of this
Agreement.

                    [SIGNATURES APPEAR ON THE FOLLOWING PAGE]



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         This Agreement is executed as of the date first written above.

BORROWER:                                        LENDER:

THE ULTIMATE SOFTWARE GROUP, INC.                SILICON VALLEY BANK


By:   /s/ MITCHELL K. DAUERMAN                    By:  /s/ CHRISTOPHER L. JONES
    ----------------------------------------          --------------------------
Name: MITCHELL K. DAUERMAN                        Name: CHRISTOPHER L. JONES
      --------------------------------------            -----------------------
Title: CHIEF FINANCIAL OFFICER AND TREASURER      Title: SENIOR VICE PRESIDENT
       -------------------------------------             ----------------------


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                                    EXHIBIT D
                             COMPLIANCE CERTIFICATE

TO:               SILICON VALLEY BANK
                  3003 Tasman Drive
                  Santa Clara, CA 95054

FROM:             The Ultimate Software Group, Inc.

         The undersigned authorized officer of The Ultimate Software Group, Inc.
("Borrower") certifies that under the terms and conditions of the Loan and
Security Agreement between Borrower and Bank (the "Agreement"), (i) Borrower is
in complete compliance for the period ending _______________ with all required
covenants except as noted below and (ii) all representations and warranties in
the Agreement are true and correct in all material respects on this date.
Attached are the required documents supporting the certification. The Officer
certifies that these are prepared in accordance with Generally Accepted
Accounting Principles (GAAP) consistently applied from one period to the next
except as explained in an accompanying letter or footnotes. The Officer
acknowledges that no borrowings may be requested at any time or date of
determination that Borrower is not in compliance with any of the terms of the
Agreement, and that compliance is determined not just at the date this
certificate is delivered.

PLEASE INDICATE COMPLIANCE STATUS BY CIRCLING YES/NO UNDER "COMPLIES" COLUMN.

<TABLE>
<CAPTION>

REPORTING COVENANT                                            REQUIRED                       COMPLIES
------------------                                            --------                       --------

<S>                                                           <C>                            <C>     <C>
Monthly financial statements + CC                             Monthly within 30 days         Yes     No
Annual (Audited)                                              FYE within 120 days            Yes     No
A/R Agings (when borrowing)                                   Monthly within 30 days         Yes     No
Borrowing Base Certificate (when borrowing)                   Monthly within 30 days         Yes     No


FINANCIAL COVENANT                          REQUIRED                   ACTUAL                COMPLIES
------------------                          --------                   ------                --------

Maintain on a Monthly Basis:
    Minimum Quick Ratio                       1.75:1.00                 _____:1.00            Yes    No
    Minimum Liquidity                       $12,000,000                $_____                 Yes    No

Have there been updates to Borrower's intellectual property, if appropriate?                  Yes    No
Has Borrower added any new offices or business locations since the prior
compliance certificate?                                                                       Yes    No
</TABLE>


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                    BANK USE ONLY


Received by:
             ---------------------------------------
                  AUTHORIZED SIGNER


Date:
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Verified:
          ------------------------------------------
                  AUTHORIZED SIGNER


Date:
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Compliance Status:                        Yes     No
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COMMENTS REGARDING EXCEPTIONS:  See Attached.

Sincerely,


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