DIGITAL GENERATION SYSTEMS INC
SC 13D/A, 1998-05-18
ADVERTISING AGENCIES
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<PAGE>
 
                                 UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                  SCHEDULE 13D

                   UNDER THE SECURITIES EXCHANGE ACT OF 1934
                              (AMENDMENT NO. 1 )*

                        Digital Generation Systems, Inc.
- --------------------------------------------------------------------------------
                                (Name of Issuer)

                                  Common Stock
- --------------------------------------------------------------------------------
                         (Title of Class of Securities)

                                  253921 10 0
- --------------------------------------------------------------------------------
                                 (CUSIP Number)

                                Robert C. Bensky
                       c/o Technology Crossover Ventures
                 56 Main Street, Suite 210, Millburn, NJ 07041
                                 (973) 467-5320
- --------------------------------------------------------------------------------
                                        
(Name, Address and Telephone Number of Person Authorized to Receive Notices and
                                Communications)

                                August 26, 1997
- --------------------------------------------------------------------------------
            (Date of Event which Requires Filing of this Statement)

If the filing person has previously filed a statement on Schedule 13G to report
the acquisition that is the subject of this Schedule 13D, and is filing this
schedule because of Rule 13d-1(e), 13d-1(f) or 13d-1(g), check the following box
[_].

NOTE: Schedules filed in paper format shall include a signed original and five
copies of the schedule, including all exhibits. See Rule 13d-7(b) for other
parties to whom copies are to be sent.

*The remainder of this cover page shall be filled out for a reporting person's
initial filing on this form with respect to the subject class of securities, and
for any subsequent amendment containing information which would alter
disclosures provided in a prior cover page.

The information required on the remainder of this cover page shall not be deemed
to be "filed" for the purpose of Section 18 of the Securities Exchange Act of
1934 ("Act") or otherwise subject to the liabilities of that section of the Act
but shall be subject to all other provisions of the Act (however, see the
Notes).
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 2 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TECHNOLOGY CROSSOVER VENTURES, L.P.
      SEE ITEM 2 FOR IDENTIFICATION OF GENERAL PARTNER
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      WC
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Delaware

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            440,594 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             440,594 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      440,594 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      3.5%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      PN

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

(A)  Excludes an aggregate of 691,863 shares owned beneficially by the other
     reporting persons indicated in this Schedule 13D, as to which this
     reporting person disclaims beneficial ownership.  Includes 262,128 shares
     of Series A Convertible Preferred Stock which are immediately convertible
     into Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 3 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TECHNOLOGY CROSSOVER VENTURES, C.V.
      SEE ITEM 2 FOR LIST OF GENERAL PARTNERS
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      WC
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Netherlands Antilles

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            34,892 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             34,892 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      34,892 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      0.3%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      PN

- ------------------------------------------------------------------------------
(A) Excludes an aggregate of 1,097,565 shares owned beneficially by the other
    reporting persons indicated in this Schedule 13D, as to which this reporting
    person disclaims beneficial ownership.  Includes 20,758 shares of Series A
    Convertible Preferred Stock which are immediately convertible into Common
    Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 4 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TECHNOLOGY CROSSOVER MANAGEMENT, L.L.C.
      SEE ITEM 2 FOR LIST OF MANAGING MEMBERS
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      OO
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Delaware

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            475,486 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             475,486 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      475,486 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      3.8%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      OO

- ------------------------------------------------------------------------------
(A)  Excludes an aggregate of 656,971 shares owned beneficially by the other
     reporting persons indicated in this Schedule 13D, as to which this
     reporting person disclaims beneficial ownership.  Includes 282,886 shares
     of Series A Convertible Preferred Stock which are immediately convertible
     into Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 5 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TECHNOLOGY CROSSOVER VENTURES II, L.P.
      SEE ITEM 2 FOR IDENTIFICATION OF GENERAL PARTNER
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      WC
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Delaware

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            314,278 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             314,278 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      314,278 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      2.5%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      PN

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

(A) Excludes an aggregate of 818,179 shares owned beneficially by the other
    reporting persons indicated in this Schedule 13D, as to which this reporting
    person disclaims beneficial ownership.  Includes 270,650 shares of Series A
    Convertible Preferred Stock which are immediately convertible into Common
    Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 6 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TCV II (Q), L.P.
      SEE ITEM 2 FOR IDENTIFICATION OF GENERAL PARTNER
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      WC
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Delaware

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            241,619 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             241,619 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      241,619 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      1.9%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      PN

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

(A)  Excludes an aggregate of 890,838 shares owned beneficially by the other
     reporting persons indicated in this Schedule 13D, as to which this
     reporting person disclaims beneficial ownership.  Includes 208,079 shares
     of Series A Convertible Preferred Stock which are immediately convertible
     into Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 7 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TCV II STRATEGIC PARTNERS, L.P.
      SEE ITEM 2 FOR IDENTIFICATION OF GENERAL PARTNER
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      WC
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Delaware

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            42,880 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             42,880 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      42,880 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      0.4%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      PN

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

(A)  Excludes an aggregate of 1,089,577 shares owned beneficially by the other
     reporting persons indicated in this Schedule 13D, as to which this
     reporting person disclaims beneficial ownership.  Includes 36,927 shares of
     Series A Convertible Preferred Stock which are immediately convertible into
     Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 8 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TECHNOLOGY CROSSOVER VENTURES II, C.V.
      SEE ITEM 2 FOR A LIST OF GENERAL PARTNERS
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      WC
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Netherlands Antilles

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            47,986 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             47,986 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      47,986 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      0.4%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      PN

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

(A)  Excludes an aggregate of 1,084,471 shares owned beneficially by the other
     reporting persons indicated in this Schedule 13D, as to which this
     reporting person disclaims beneficial ownership.  Includes 41,323 shares of
     Series A Convertible Preferred Stock which are immediately convertible into
     Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 9 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TCV II, V.O.F
      SEE ITEM 2 FOR A LIST OF MANAGING GENERAL PARTNERS
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      WC
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Netherlands Antilles

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            10,208 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             10,208 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      10,208 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      0.1%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      PN

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

(A)  Excludes an aggregate of 1,122,249 shares owned beneficially by the other
     reporting persons indicated in this Schedule 13D, as to which this
     reporting person disclaims beneficial ownership.  Includes 8,792 shares of
     Series A Convertible Preferred Stock which are immediately convertible into
     Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 10 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
 1    NAME OF REPORTING PERSON  TECHNOLOGY CROSSOVER MANAGEMENT II, L.L.C.
      SEE ITEM 2 FOR A LIST OF MANAGING MEMBERS
      I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      OO
- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      Delaware

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            656,971 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          0 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             656,971 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      656,971 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [X]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      5.1%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      OO

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

(A)  Excludes an aggregate of 475,486 shares owned beneficially by the other
     reporting persons indicated in this Schedule 13D, as to which this
     reporting person disclaims beneficial ownership.  Includes 565,771 shares
     of Series A Convertible Preferred Stock which are immediately convertible
     into Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 11 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
      NAME OF REPORTING PERSON  JAY C. HOAG
 1    I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3

- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      00

- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      U.S. Citizen

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            0 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          1,132,457 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             1,132,457 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      1,132,457 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [_]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      8.7%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      IN

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

(A)   Includes 848,657 shares of Series A Convertible Preferred Stock which are
      immediately convertible into Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 12 OF 18 PAGES
- ------------------------------------------------------------------------------
 
- ------------------------------------------------------------------------------
      NAME OF REPORTING PERSON  RICHARD H. KIMBALL
 1    I.R.S. IDENTIFICATION NO. OF ABOVE PERSON (ENTITIES ONLY)

- ------------------------------------------------------------------------------
      CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP  (SEE INSTRUCTIONS)
 2                                                              (a) [_]
                                                                (b) [X]
 
- ------------------------------------------------------------------------------
      SEC USE ONLY
 3
 
- ------------------------------------------------------------------------------
      SOURCE OF FUNDS  (SEE INSTRUCTIONS)
 4    
      OO

- ------------------------------------------------------------------------------
      CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO
 5    ITEMS 2(d) or 2(e)                                                   [_]
 
      
- ------------------------------------------------------------------------------
      CITIZENSHIP OR PLACE OF ORGANIZATION
 6    
      U.S. Citizen

- ------------------------------------------------------------------------------
                          SOLE VOTING POWER
                     7   
     NUMBER OF            0 (A)
 
      SHARES       -----------------------------------------------------------
                          SHARED VOTING POWER
   BENEFICIALLY      8
                          1,132,457 (A)
     OWNED BY
                   -----------------------------------------------------------
       EACH               SOLE DISPOSITIVE POWER
                     9    
    REPORTING             1,132,457 (A)
 
      PERSON       -----------------------------------------------------------
                          SHARED DISPOSITIVE POWER
       WITH         10
                          0 (A)
- ------------------------------------------------------------------------------
      AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON
11  
      1,132,457 (A)

- ------------------------------------------------------------------------------
      CHECK IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES   [_]
12    (SEE INSTRUCTIONS)
      
 
- ------------------------------------------------------------------------------
      PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)
13    
      8.7%

- ------------------------------------------------------------------------------
      TYPE OF REPORTING PERSON (SEE INSTRUCTIONS)
14
      IN

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

(A)  Includes 848,657 shares of Series A Convertible Preferred Stock which are
     immediately convertible into Common Stock on a one-to-one basis.
<PAGE>
 
                                 SCHEDULE 13D


- ------------------------------------------------------------------------------
 CUSIP NO. 253921 10 0                                     PAGE 13 OF 18 PAGES
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Defined Terms.
- ------------- 

  Capitalized terms not otherwise defined herein shall have the meanings given
them in the original Schedule 13D relating to the Common Stock of the Issuer
filed by the undersigned with the Commission on September 5, 1997 (file number
005-49603).

  Item 1.           
            Security and Issuer.    
            -------------------          

  The title of the class of securities to which this Schedule 13D relates is
Common Stock ("Common Stock") of Digital Generation Systems, Inc., a California
corporation (the "Issuer"). This Schedule 13D also relates to Common Stock 
issuable upon the conversion of Series A Convertible Preferred Stock (which
currently is convertible on a 1:1 basis). The principal executive offices of
the Issuer are located at 875 Battery Street, Suite 1850, San Francisco, CA
94111

  Item 3.
            Source and Amount of Funds or Other Consideration.
            ------------------------------------------------- 

  All of the securities of the Issuer disclosed on the cover pages to this
Schedule 13D are held of record by the entities listed below.  The source of
funds used in the acquisition of such securities, in each case, was the general
working capital of such entities.  Such working capital was contributed by such
entities' respective partners.

<TABLE>
<CAPTION>
                               Aggregate
                               ---------
                               Number of     Aggregate      Weighted Average  
                               ---------     ---------      ----------------
Holder                         Shares(1)    Amount Paid      Price Per Share      
- -------                        ----------   ------------     ---------------
<S>                            <C>          <C>             <C>
TCV I, L.P.                       440,594     $2,134,344              $4.84
TCV I, C.V.                        34,892     $  169,034              $4.84
TCV II, V.O.F.                     10,208     $   35,743              $3.50
TCV II, L.P.                      314,278     $1,100,425              $3.50
TCV II (Q)                        241,619     $  846,015              $3.50
TCV II Strategic Partners          42,880     $  150,142              $3.50
TCV II, C.V.                       47,986     $  168,019              $3.50
Totals                          1,132,457     $4,603,722              $4.07
</TABLE>
- ------------------------------------------
(1) Includes both open market purchases of Common Stock and Series A Convertible
    Preferred Stock purchased from the Issuer in a private placement
    transaction.
 
Item 5.
            Interest in Securities of the Issuer.
            ------------------------------------  

  (a) and (b) Except to the extent otherwise expressly stated herein, this
Schedule 13D shall not be construed as an admission that any Item 2 Person is,
either for purposes of Section 13(d) or 13(g) of the Act or for other purposes,
the beneficial owner of any Common Stock disclosed in this Schedule 13D. The
aggregate number and percentage of the class of securities identified pursuant
to 
<PAGE>
 
                                 SCHEDULE 13D


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 CUSIP NO. 253921 10 0                                     PAGE 14 OF 18 PAGES
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Item 1 of this Schedule 13D that, pursuant to Rule 13d-3, may be deemed to be
beneficially owned by each Item 2 Person are as follows:

<TABLE>
<CAPTION>
                                    
                           Common Stock 
                           ------------          
                           Beneficially                                   Dispositive
                           ------------                                   -----------
   Item 2 Person              Owned        % of Class(1)   Voting Power      Power
   -------------              -----        -------------   ------------      -----
<S>                           <C>          <C>             <C>               <C>
TCV I, L.P. (2)              440,594          3.5%            sole            sole 
TCV I, C.V. (2)               34,892          0.3%            sole            sole 
TCM I                        475,486          3.8%            sole            sole 
TCA I                              0            0%            N/A             N/A  
TCV II, L.P. (3)             314,278          2.5%            sole            sole 
TCV II (Q)  (3)              241,619          1.9%            sole            sole 
TCV II Strategic              42,880          0.4%            sole            sole 
 Partners  (3)                                                                     
TCV II, C.V. (3)              47,986          0.4%            sole            sole 
TCV II, V.O.F.(3)             10,208          0.1%            sole            sole 
TCM II                       656,971          5.1%            sole            sole 
TCA II                             0            0%            N/A             N/A  
Hoag (4)                   1,132,457          8.7%            shared          sole 
Kimball (4)                1,132,457          8.7%            shared          sole  
</TABLE>

____________________________________
    (1)
          All percentages in this table are based, pursuant to Rule 13d-1(j) of
  the Securities Exchange Act of 1934, on the 12,210,625 shares of Common Stock
  of the Company outstanding as of March 27, 1998, as reported in the Company's
  Annual Report on Form 10-K for the fiscal year ended December 31, 1997, and on
  the shares of Series A Convertible Preferred Stock of the Company beneficially
  owned by the listed Item 2 Persons which have been included on an as-converted
  to Common Stock basis.

    (2)
          Each noted entity (together, the "TCV I Funds") is the holder of
  record of the securities set forth opposite the name of such entity and has
  sole voting and investment power with respect to such securities.  TCM I, as
  sole General Partner of TCV I, L.P. and as Investment General Partner of TCV
  I, C.V., may also be deemed to have sole voting and investment power with
  respect to such securities.  TCM I disclaims beneficial ownership of such
  securities except to the extent of its pecuniary interest therein.

     (3)
          Each noted entity (together, the "TCV II Funds") is the holder of
  record of the securities set forth opposite the name of such entity and has
  sole voting and investment power with respect to such securities.  TCM II, as
  sole General 
<PAGE>
 
                                 SCHEDULE 13D


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 CUSIP NO. 253921 10 0                                     PAGE 15 OF 18 PAGES
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  Partner of TCV II, L.P., TCV II (Q) and TCV II Strategic Partners and as
  Investment General Partner of TCV II, C.V. and TCV II, V.O.F., may also be
  deemed to have sole voting and investment power with respect to such
  securities. TCM II disclaims beneficial ownership of such securities except to
  the extent of its pecuniary interest therein.

    (4)
          Under the operating agreements of both TCM I and TCM II, Hoag and
  Kimball have the independent power to cause the funds managed by such entities
  to buy and sell securities of publicly traded portfolio companies, however, in
  general, they must act by unanimous consent with respect to all other matters,
  including directing the voting of such securities.  As a result, Hoag and
  Kimball may also be deemed to have sole dispositive power and shared voting
  power with respect to the securities held by the TCV I Funds and the TCV II
  Funds.  Hoag and Kimball disclaim beneficial ownership of such securities
  except to the extent of their respective pecuniary interests therein.
 
(c)       The following is a list of all transactions in the Issuer's securities
by the Item 2 Persons effected during the past sixty days. All of such
transactions were open market transactions.

<TABLE>
<CAPTION>

                                                                                       
                                                      Aggregate Percentage Ownership   
                                                      ------------------------------
                                             Price     of All Item 2 Persons After  
                                             -----     --------------------------
                                Shares       Per      Transactions Effected  on Date   
                                ------       ---      ------------------------------
  Purchaser            Date    Purchased     Share                Listed               
  ---------            ----    ---------     ------               ------               
<S>                   <C>      <C>           <C>                  <C> 
TCV I, L.P.           5-6-98      10,749      $3.75               8.7%(1)               
TCV I, C.V.           5-6-98         851      $3.75               8.7%(1)               
TCV II, V.O.F.        5-6-98         363      $3.75               8.7%(1)               
TCV II, L.P.          5-6-98      11,194      $3.75               8.7%(1)               
TCV II (Q)            5-6-98       8,606      $3.75               8.7%(1)               
TCV II Strategic      5-6-98       1,528      $3.75               8.7%(1)               
 Partners                                                                               
TCV II, C.V.          5-6-98       1,709      $3.75               8.7%(1)               
</TABLE>

___________________________________
     (1)  
          This percentage is based, pursuant to Rule 13d-1(j) of the Securities
  Exchange Act of 1934, on the 12,210,625 shares of Common Stock of the Company
  outstanding as of March 27, 1998, as reported in the Company's Annual Report
  on Form 10-K for the fiscal year ended December 31, 1997, and on the shares of
  Series A Convertible Preferred Stock of the Company beneficially owned by the
  listed Item 2 Persons which have been included on an as-converted to Common
  Stock basis.

  (d)     Inapplicable.

  (e)     Inapplicable.
<PAGE>
 
                                 SCHEDULE 13D


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 CUSIP NO. 253921 10 0                                     PAGE 16 OF 18 PAGES
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Item 7.
     Material to be Filed as Exhibits.
     -------------------------------- 

  The following exhibit was filed as Exhibit A to the Schedule 13D relating to
the Common Stock of the Issuer filed by the undersigned with the Commission on
September 5, 1997 and is hereby incorporated herein by reference:

  A - Statement Appointing Designated Filer and Authorized Signer dated
      September 5, 1997

  The following exhibits were filed with the Commission by the Issuer as
Exhibits 2.2 and 2.3 to its Current Report on Form 8-K on August 1, 1997 and are
incorporated herein by reference.

  B - Preferred Stock Purchase Agreement by and among Digital Generation
      Systems, Inc. and the parties named therein, dated as of July 14, 1997.

  C - Amendment to Preferred Stock Purchase Agreement, dated as of July 23,
      1997.
<PAGE>
 
                                 SCHEDULE 13D


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 CUSIP NO. 253921 10 0                                     PAGE 17 OF 18 PAGES
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                                   SIGNATURE

  After reasonable inquiry and to the best of my knowledge and belief, I certify
that the information set forth in this statement is true, complete and correct.

Dated May 18, 1998

TECHNOLOGY CROSSOVER VENTURES, L.P.,
a Delaware Limited Partnership

By:     /s/ Robert C. Bensky
      ----------------------
     Robert C. Bensky, Authorized Signatory

TECHNOLOGY CROSSOVER VENTURES, C.V.,
a Netherlands Antilles Limited Partnership

By:     /s/ Robert C. Bensky
      ----------------------
     Robert C. Bensky, Authorized Signatory

TECHNOLOGY CROSSOVER MANAGEMENT, L.L.C.,
a Delaware Limited Liability Company
 
By:    /s/ Robert C. Bensky
     ----------------------
   Robert C. Bensky, Authorized Signatory

TECHNOLOGY CROSSOVER VENTURES II, L.P.,
a Delaware Limited Partnership

By:    /s/ Robert C. Bensky
     ----------------------
   Robert C. Bensky, Authorized Signatory

TCV II (Q), L.P.,
a Delaware Limited Partnership

By:   /s/ Robert C. Bensky
    ----------------------
   Robert C. Bensky, Authorized Signatory

TCV II STRATEGIC PARTNERS, L.P.,
a Delaware Limited Partnership

By:    /s/ Robert C. Bensky
     ----------------------
   Robert C. Bensky, Authorized Signatory

TECHNOLOGY CROSSOVER VENTURES II, C.V.,
a Netherlands Antilles Limited Partnership

By:    /s/ Robert C. Bensky
     ----------------------
   Robert C. Bensky, Authorized Signatory

TCV II, V.O.F.,
a Netherlands Antilles General Partnership

By:    /s/ Robert C. Bensky
     ----------------------
   Robert C. Bensky, Authorized Signatory
<PAGE>
 
                                 SCHEDULE 13D


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 CUSIP NO. 253921 10 0                                     PAGE 18 OF 18 PAGES
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TECHNOLOGY CROSSOVER MANAGEMENT II, L.L.C.,
a Delaware Limited Liability Company

By:    /s/ Robert C. Bensky
     ----------------------
   Robert C. Bensky, Authorized Signatory

Jay C. Hoag

By:    /s/ Robert C. Bensky
     ----------------------
   Robert C. Bensky, Authorized Signatory

Richard H. Kimball

By:    /s/ Robert C. Bensky
     ----------------------
   Robert C. Bensky, Authorized Signatory


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