<PAGE>

                                                                   EXHIBIT 10.19

[LOGO] Silicon Valley Bank

AMENDMENT TO QUICKSTART LOAN AND SECURITY AGREEMENT

Borrower: DOCENT, INC.                 Address:     444 Castro Street, Suite 440
                                                    Mountain View, CA 94041
Date:     October 31, 1997

THIS AMENDMENT TO QUICKSTART LOAN AND SECURITY AGREEMENT IS ENTERED INTO ON THE
ABOVE DATE BETWEEN SILICON VALLEY BANK ("SILICON"), WHOSE ADDRESS IS 3003 TASMAN
DRIVE, SANTA CLARA, CALIFORNIA 95054 AND THE BORROWER NAMED ABOVE (JOINTLY AND
SEVERALLY, THE "BORROWER"), WHOSE CHIEF EXECUTIVE OFFICE IS LOCATED AT THE ABOVE
ADDRESS ("BORROWER'S ADDRESS").

          The parties hereto agree to amend the QuickStart Loan and Security
Agreement between them dated August 1, 1997 (the "Loan Agreement"), effective
as of the date hereof, as follow: Capitalized terms used but not defined herein
shall have the same meanings set forth in the Loan Agreement.

          1.   Amended Schedule. The Schedule to QuickStart Loan and Security
Agreement (Letters of Credit Sublimit is replaced, effective on the date hereof,
with the Amended Schedule XXX QuickStart Loan and Security Agreement (Merchant
Services Sublimit) attached hereto.

          2.   Representations True. Borrower represents and warrants to Silicon
that all representations and warranties set forth in the Loan Agreement, as
amended hereby, are true and correct.

          3.   General Provisions. This Amendment, the Loan Agreement, and any
prior written amendments to the Loan Agreement signed by Silicon and the
Borrower, and other written documents between Silicon and Borrower set forth in
full all of the representations and agreements, of the parties with respect to
the subject matter hereof and supersede all prior discussions, representation
agreements, and understandings between the parties with respect to the subject
matter hereof. Except as expressly amended, all of the terms and provisions of
the Loan Agreement, and all other documents and agreement between Silicon and
Borrower shall remain in full force and effect and the same are hereto ratified
and confirmed.

   Borrower:
        DOCENT, INC.


        By /s/ Julia A. O'Connor
          ---------------------------------------
              President or Vice President


   Silicon:
        SILICON VALLEY BANK


        By /s/ [ILLEGIBLE]
          ---------------------------------------
              Title Vice President
                   ------------------------------
<PAGE>

[LOGO] Silicon Valley Bank

Amended Schedule to
QuickStart Loan and Security Agreement (Merchant Services Sublimit)

BORROWER:     DOCENT, INC.

DATE:         October 31, 1997

      THIS AMENDED SCHEDULE REPLACES THE "SCHEDULE TO QUICKSTART LOAN AND
SECURITY AGREEMENT (LETTERS OF CREDIT SUBLIMIT)" and is an integral part of the
Loan and Security Agreement between Silicon Valley Bank ("Silicon") and the
above-named borrower ("Borrower") date as of August 1, 1997, as may be amended.

Merchant Services/
Business Credit Card
Sublimit (Section 1):    The aggregate Credit Limit shall be reduced by an
                         amount equal to the sum of $20,000.00 (the "Merchant
                         Service Reserve"). Silicon may, in its sole discretion,
                         charge as Loans, any amounts that may become due or
                         owing to Silicon in connection with merchant credit
                         card processing services furnished to Borrower by or
                         through Silicon (the "Credit Card Services"), Borrower
                         shall execute all standard form applications and
                         agreements, including without limitation, the
                         Indemnification and Pledge Agreement of Silicon in
                         connection with the Credit Card Services and, without
                         limiting any of the terms of such applications and
                         agreements, Borrower will pay all standard fees and
                         charges of Silicon in connection with the Credit Card
                         Services and, without limiting any of the terms of such
                         applications and agreements, Borrower will pay all
                         standard fees and charges of Silicon in connection with
                         the Credit Card Services.

Maturity Date (Section 4):    February 1, 1999


Borrower:                                    Silicon:
DOCENT, INC.                                 SILICON VALLEY BANK


By: /s/ Julia A. O'Connor                    By: /s/ [ILLEGIBLE]
   ----------------------------------        --------------------------------
       President or Vice President           Title  Vice President
                                             --------------------------------
<PAGE>

           Agreement Regarding Merchant Services/Business VISA Program

Client Name: Docent Software, Inc.

Service Type:

 .    Merchant Services (through Bank of America)
        Merchant #: 43013 435 515 __ __ __ __ __

 .    Business VISA (Processor:____________________ )
        Cardholders: (attach list if more than three names)
        1)________________________________  Credit Limit: _________________
        2)________________________________  Credit Limit: _________________
        3)________________________________  Credit Limit: _________________

Type of Coverage:

 .    Subfacility of existing line of credit
Line Amount: $750,000.00 Expiration Date: February 1, 1999
Reserve Amount: $20,000.00
                ----------
 .    Certificate of Deposit
        Amount:________________Certificate #.______________ Term:______________

The undersigned hereby indemnifies and holds Silicon Valley Bank ("SVB")
harmless from and against any and all claims, demands, liabilities, charges,
claims, costs, losses, damages, and expenses (including attorney's fees)
(collectively, the "Liabilities"), if any, that SVB incurs or may incur in
connection with the Merchant Services and/or Business VISA program referenced
above, To secure its obligations to SVB, the undersigned pledges and assigns to
SVB. and grants to SVB a security interest in, the above referenced certificate
of deposit(s) (the "Collateral"); and agrees that SVB, to satisfy all or any
portion of the Liabilities, may at any time or from time to time, exercise any
and all rights and remedies against said Collateral, all without notice to or
demand upon the undersigned, The undersigned further agrees that SVB may at
SVB's options, without notice or demand, pay any outstanding Liabilities by
charging such amount and/or making reserves against any line-of-credit the
undersigned may have with SVB, The foregoing agreements, indemnification
obligations, and pledge, assignment, and security interest grant shall survive
termination of the underlying programs.

Client Name: Docent Software, Inc.
            ---------------------

By: /s/ Julia A. O'Connor                 By:
   --------------------------------          _________________________________
Title: VP and CFO                         Title:
      -----------------------------             ______________________________
Date:  11/4/97                            Date:
     ------------------------------             ______________________________
<PAGE>

[LOGO] Silicon Valley Bank

QUICKSTART LOAN AND SECURITY AGREEMENT

Borrower: Docent, Inc.                Address:    444 Castro St. Suite 440
          -----------------------                 ------------------------------
Date:     August l, 1997                          Mountain View, CA 94041
         ------------------------                 ------------------------------

SILICON'S OFFER TO EXTEND FINANCING ON THE TERMS SET FORTH HEREIN SHALL EXPIRE
IF THIS AGREEMENT IS NOT EXECUTED BY BORROWER AND RETURNED TO SILICON WITHIN 30
DAYS OF THE ABOVE DATE.

THIS LOAN AND SECURITY AGREEMENT is entered into on the above date between
SILICON VALLEY BANK ("Silicon"), whose address is 3003 Tasman Drive, Santa
Clara, California 95054 and the borrower named above (joint and severally, the
"Borrower"), whose chief executive office is located at the above address
("Borrower's Address").

1.   Loans. Silicon will make loans to Borrower (the "Loans") in amounts
determined by Silicon in its reasonable business judgment up to the amount (the
"Credit Limit") shown on the Schedule to this Agreement (the "Schedule"),
provided no Event Default and no event which, with notice or passage of time or
both would constitute an Event of Default has occurred. All Loans and other
monetary Obligations will bear interest at the rate shown on the Schedule.
Interest will be payable monthly, on the date shown on the monthly billing from
Silicon. Silicon may, in its discretion, charge interest to Borrower's deposit
accounts maintained with Silicon.

2.   Security Interest. As security for all present and future indebtedness,
guarantees, Liabilities, and other obligations, of Borrower to Silicon
(collectively, the "Obligations"), Borrower hereby grants Silicon a continuing
security interest in all of Borrower's interest in the following types of
property, whether now owned or hereafter acquired, and wherever located
(collectively, the "Collateral"): All "accounts," "general intangibles,"
"contract rights," "chattel paper," "documents," "letters of credit,"
"instruments," "deposit accounts," "inventory," "farm products, "investment
property," "fixtures" and "equipment," as such terms defined in Division 9 of
the California Uniform Commercial Code in effect on the date hereof, and all
products, proceeds and insurance proceeds of the foregoing.

3.   Representations and Agreements Of Borrower. Borrower represents to Silicon
as follows, and Borrower agrees that the following representations will continue
to be true, and that Borrower will comply with all of the following agreements
throughout the term of this Agreement:

   3.1  Corporate Existence and Authority. Borrower, if a corporation, is and
will continue to be, duly authorized, validly existing and in good standing
under the laws of the jurisdiction of its incorporation The execution, delivery
and performance by Borrower of this Agreement, and all other documents
contemplated hereby have been duly and validly authorized, and do not violate
any law or any provision of, and are not grounds for acceleration under, any
agreement or instrument which is binding upon Borrower.

   3.2  Name; Places of Business. The name of Borrower set forth in this
Agreement is its correct name. Borrower shall give Silicon l5 days' prior
written notice before changing its name. The address set forth in the heading to
this Agreement is Borrower's chief executive office. In addition, Borrower has
places of business and Collateral is located only at the locations set forth on
the Schedule. Borrower will give Silicon at least 15 days prior written notice
before changing its chief executive office or locating the Collateral: any other
location.

   3.3  Collateral. Silicon has and will at all times continue to have a
first-priority perfected security interest in all of the Collateral other than
specific equipment. Borrower will immediately advise Silicon in writing of any
material loss or damage to the Collateral.

   3.4  Financial Condition and Statements. All financial statements now or in
the future delivered to Silicon have been, and will be, prepared in conformity
with generally accepted accounting principles. Since the last date covered by
any such statement, there has been no material adverse change in the financial
condition or business of Borrower. Borrower will provide Silicon: (i) within 30
days after the end of each mouth, a monthly financial statement prepared by
Borrower, and such other information as Silicon shall reasonably request; (ii)
within 120 days following the end of Borrower's fiscal year, complete annual
financial statements, certified by independent certified public accountants
acceptable to Silicon and accompanied by the unqualified report thereon by said
independent certified public accountants; and (iii) other financial information
reasonably requested by Silicon from time to time.

   3.5  Taxes; Compliance with Law. Borrower has filed and will file, when due,
all tax returns and reports required by applicable law, and Borrower has paid,
and will pay, when due, all taxes, assessments, deposits and contributions now
or in the future owed by Borrower. Borrower has complied and will comply, in all
material respects, with all applicable news, rules and regulations.

   3.6  Insurance. Borrower shall at all times insure all of the tangible and
personal property Collateral and carry such other business insurance as is
customary in Borrower's industry.

   3.7  Access to Collateral and Books and Records. At reasonable times, on one
business day notice, Silicon, or its

                                      -1-
<PAGE>

Silicon Valley Bank                       QuickStart Loan and Security Agreement
--------------------------------------------------------------------------------

agents, shall have the right to inspect the Collateral, and the right to audit
and copy Borrower's books and records.

      3.8 Operating Account. Borrower shall maintain its primary operating
accounts with Bank.

      3.9 Additional Agreement. Borrower shall not, without Silicon's prior
written consent, do any of the following: (i) enter into any transaction outside
the ordinary course of business except for the sale of capital stock to venture
investors, provided that Borrower promptly delivers written notification to
Silicon of any such sale; (ii) sell or transfer any Collateral, except in the
ordinary course of business; (iii) pay or declare any dividends on Borrower's
stock (except for dividends payable solely in stock of Borrower); or (iv)
redeem, retire, purchase or otherwise acquire, directly or indirectly, any of
Borrower's stock other than the repurchase of up to five percent (5%) of
Borrower's then issued stock in any fiscal year from Borrower's employees or
directors pursuant to written agreement with Borrower.

4. Term. This Agreement shall continue in effect until the maturity date set
forth on the Schedule (the "Maturity Date"). This Agreement may be terminated,
without penalty, prior to the Maturity Date as follows: (i) by Borrower,
effective three business days after written notice of termination is given to
Silicon; or (ii) by Silicon at any time after the occurrence of an Event of
Default, without notice, effective immediately. On the Maturity Date or on any
earlier effective date of termination, Borrower shall pay all Obligations in
full, whether or not such Obligations are otherwise then due and payable. No
termination shall in any way affect or impair any security interest or other
right or remedy of Silicon, nor shall any such termination relieve Borrower of
any Obligation to Silicon, until all of the Obligations have been paid and
performed in full.

5. Events of Default and Remedies. The occurrence of any of the following events
shall constitute an "Event of Default" under this Agreement: (a) Any
representation, statement, report or certificate given to Silicon by Borrower or
any of its officers, employees or agents, now or in the future, is untrue or
misleading in a material respect; or (b) Borrower fails to pay when due any Loan
or any interest thereon or any other monetary Obligation; or (c) the total
Obligations outstanding at any time exceed the Credit Limit; or (d) Borrower
fails to perform any other non-monetary Obligation, which failure is not cured
within 5 business days after the date due; or (e) Dissolution, termination of
existence, failure of Borrower, or appointment of a receiver, trustee or
custodian, for all or any part of the property of, assignment for the benefit of
creditors by, or the commencement of any proceeding by or against Borrower under
any reorganization, bankruptcy, insolvency, arrangement, readjustment of debt,
dissolution or liquidation law or statute of any jurisdiction, now or in the
future in effect; or (f) a material adverse change in the business, operations,
or financial or other condition of Borrower. If an Event of Default occurs,
Silicon, shall have the right to accelerate and declare all of the Obligations
to be immediately due and payable, increase the interest rate by an additional
four percent per annum, and exercise all rights and remedies accorded it by
applicable law.

6. General. If any provision of this Agreement is held to be unenforceable, the
remainder of this Agreement shall still continue in full force and effect. This
Agreement and any other written agreements, documents and instruments executed
in connection herewith are the complete agreement between Borrower and Silicon
and supersede all prior and contemporaneous negotiations and oral
representations and agreements, all of which are merged and integrated in this
Agreement. There are no oral understandings, representations or agreements
between the parties which are not in this Agreement or in other written
agreements signed by the parties in connection this Agreement. The failure of
Silicon at any time to require Borrower to comply strictly with any of the
provisions of this Agreement shall not waive Silicon's right later to demand and
receive strict compliance. Any waiver of a default shall not waive any other
default. None of the provisions of this Agreement may be waived except by a
specific written waiver signed by an officer of Silicon and delivered to
Borrower. The provisions of this Agreement may not be mended, except in a
writing signed by Borrower and Silicon. Borrower shall reimburse Silicon for all
reasonable attorneys' fees and all other reasonable costs incurred by Silicon,
in connection with this Agreement (whether or not a lawsuit is filed). If
Silicon or Borrower files any lawsuit against the other predicated on a breach
of this Agreement, the prevailing party shall be entitled to recover its
reasonable costs and attorneys' fees from the non-prevailing party. Borrower may
not assign any rights under this Agreement without Silicon's prior written
consent This Agreement shall be governed by the laws of the State of California.

7. Mutual Waiver of Jury Trial. BORROWER AND SILICON EACH HEREBY WAIVE THE RIGHT
TO TRIAL BY JURY IN ANY ACTION OR PROCEEDING BASED UPON, ARISING OUT OF, OR IN
WAY RELATING TO, THIS AGREEMENT OR ANY CONDUCT, ACT OR OMISSION OF SILICON OR
BORROWER OR ANY OF THEIR DIRECTORS, OFFICERS, EMPLOYEES, AGENTS, ATTORNEY OR
AFFILIATES.

  Borrower:
                Docent, Inc.
       ---------------------------------


       By /s/ Pardner Wynn
          ------------------------------
           President or Vice President


  Silicon:
       SILICON VALLEY BANK


       By /s/ [ILLEGIBLE]^^
          ------------------------------
       Title           VP
             ---------------------------


                                       -2-
<PAGE>

[LOGO] Silicon Valley Bank

Schedule to
QuickStart Loan and Security Agreement (Master)

BORROWER:      Docent, Inc.
           --------------------------

DATE:          August l, 1997
           --------------------------

      This Schedule is an integral part of the Loan and Security Agreement
between Silicon Valley Bank ("Silicon") and the above-named borrower
("Borrower") of even date.

Credit Limit (Aggregate)
(Section 1):                        $750,000.00 (includes, without limitation,
                                     ----------
                                    Equipment Advances and the Merchant Services
                                    and Business Visa Reserve, if any)


Interest Rate (Section 1):          A rate equal to the "Prime Rate" in effect
                                    from time to time, plus. 0 %, per annum.
                                                            ---
                                    Interest shall be calculated on the basis of
                                    a 360-day year for the actual number of days
                                    elapsed. "Prime Rate" means the rate
                                    amounted from time to time by Silicon as its
                                    "prime rate;" it is a base rate upon which
                                    other rates charged by Silicon are based,
                                    and it is not necessarily the best rate
                                    available at Silicon. The interest rate
                                    applicable to the Obligations shall change
                                    on each date there is a change in the Prime
                                    Rate.

Maturity Date (Section 4):          February 1, 1999
                                    ----------------

Other Locations and Addresses
(Section 3.2):                      624 West Hastings Road, Spokane, WA 99218
                                    -----------------------

Other Agreements:                   Borrower also agrees as follows:

                                    1. Loan Fee. Borrower shall concurrently pay
                                    Silicon a non-refundable Loan Fee in the
                                    amount of $ 0
                                               ---

                                    2. Banking Relationship. Borrower shall at
                                    all times maintain its primary banking
                                    relationship with Silicon.

Borrower:                               Silicon:

         Docent, Inc.                   SILICON VALLEY BANK
-----------------------------


By /s/ Pardner Wynn                     By /s/ [ILLEGIBLE]^^
  ---------------------------             ----------------------------
  President or Vice President           Title    VP
                                             -------------------------
<PAGE>

[LOGO] Silicon Valley Bank

Schedule to
QuickStart Loan and Security Agreement (Equipment Advance)

BORROWER:         Docent, Inc.
                --------------------------

DATE:             August l, 1997
                --------------------------

         This Schedule is an integral part of the Loan and Security Agreement
between Silicon Valley Bank ("Silicon") and the above-named borrower
("Borrower") of even date.

Credit Limit (Equipment)
(Section 1):                   $750,000,00 (such, amount to be funded under
                                ----------
                               the aggregate Credit Limit). Equipment Advances
                               will be made only an or prior to May 1, 1998 (the
                                                                ------
                              "Last Advance Date") and only for the purpose of
                               purchasing equipment reasonably acceptable to
                               Silicon. Borrower must provide invoices for the
                               equipment to Silicon on or before the Last
                               Advance Date.


Interest Rate (Section 1):     A rate equal to the "Prime Rate" in effect from
                               time to time, plus 0 % per annum. Interest shall
                               be calculated on the basis of a 360-day year for
                               the actual number of days elapsed. "Prime Rate"
                               means the rate amounted from time to time by
                               Silicon as its "prime rate," it is a base rate
                               upon which other rates charged by Silicon are
                               based, and it is not necessarily the best rate
                               available at Silicon. The interest rate
                               applicable to the Obligations shall change on
                               each date there is a change in the Prime Rate.

Maturity Date (Section 4):     After the Last Advance Date, the unpaid principal
                               balance of the Equipment Advances shall be repaid
                               in 33 equal monthly installments of principal,
                                  --
                               plus interest, commencing on July 1, 1998 and
                                                            ------------
                               continuing on the same day of each month
                               thereafter until the entire unpaid principal
                               balance of the Equipment Advances unpaid
                               interest have been paid (subject to Silicon's
                               right to accelerate the Equipment Advances on an
                               Event of Default).



Borrower:                               Silicon:

         Docent, Inc.                   SILICON VALLEY BANK
-----------------------------


By /s/ Pardner Wynn                     By /s/ [ILLEGIBLE]^^
  ---------------------------              ----------------------------
  President or Vice President           Title    VP
                                             --------------------------
<PAGE>

[LOGO] Silicon Valley Bank

Schedule to QuickStart Loan and Security Agreement (Letters of Credit Sublimit)

BORROWER:   Docent, Inc.                  DATE:   August l, 1997
          -------------------------             --------------------------

      This Schedule is an integral part of the Loan and Security Agreement
between Silicon Valley Bank ("Silicon") and the above-named borrower
("Borrower") of even date.

Letters of Credit
Sublimit (Section 1):       The aggregate Credit limit shall be reduced by an
                            amount equal to the sum of the face amounts of all
                            outstanding letters of credit (including drawn but
                            unreimbursed letters of credit). Silicon agrees to
                            issue or cause to be issued letters of credit for
                            the account of Borrower, provided that the face
                            amount of outstanding letters of credit (including
                            drawn but unreimbursed letters of credit) shall not
                            in any case exceed Forty Thousand Dollars
                                               --------------
                            ($40,000.00). Each such letter of credit shall have
                              ---------
                            an expiry date no later than one hundred eighty
                            (180) days alter the Maturity Date as stated in the
                            Schedule to QuickStart Loan and Security Agreement
                            of even date ("Maturity Date") provided that
                            Borrower's letter of credit reimbursement obligation
                            shall be secured by cash on terms acceptable to
                            Silicon at any time after the Maturity Date. All
                            such letters of credit shall be, in form and
                            substance, acceptable to Silicon in its sole
                            discretion and shall be subject to the terms and
                            conditions of Silicon's form of application and
                            letter of credit agreement.

                            Borrower shall indemnify, defend and hold Silicon
                            harmless from any loss, cost, expense or liability,
                            including, without limitation, reasonable attorneys'
                            fees, arising out of or in connection with any
                            letters of credit.

                            Borrower may request that Silicon issue a letter of
                            credit payable in a currency other than United
                            states Dollars. If a demand for payment is made
                            under any such letter of credit, Silicon shall treat
                            such demand as an Advance to Borrower of the
                            equivalent of the amount thereof (plus cable
                            charges) in United States currency at the then
                            prevailing rate of exchange in San Francisco,
                            California, for sales of that other currency for
                            cable transfer to the country of which it is the
                            currency.

                            Upon the issuance of any letter of credit payable in
                            a currency other than United States Dollars, Silicon
                            shall create a reserve (the "Letter of Credit
                            Reserve") under the aggregate Credit Limit for
                            letters of credit against fluctuations in currency
                            exchange rates, in an amount equal to ten percent
                            (10%) of the face amount of such letter of credit.
                            The amount of such reserve may be amended by Silicon
                            from time to time to account for fluctuations in the
                            exchange rate. The availability of funds under the
                            Credit Limit shall be reduced bit the amount of such
                            reserve for so long as such letter of credit remains
                            outstanding.


Borrower:                               Silicon:

         Docent, Inc.                   SILICON VALLEY BANK
----------------------------


By /s/ Pardner Wynn                     By /s/ [ILLEGIBLE]^^
  --------------------------              ----------------------------
  President or Vice President           Title    VP
                                             -------------------------