Document:

EX-10.1

TENTH AMENDMENT TO AMENDED AND RESTATED 

LOAN AND SECURITY AGREEMENT

THIS TENTH AMENDMENT TO AMENDED AND RESTATED LOAN AND SECURITY AGREEMENT (this “Agreement”) is
entered into as of November 30, 2004, by and among SILICON VALLEY BANK, a California chartered
bank, doing business in Virginia as “Silicon Valley East” (“Bank”) with its principal place of
business at 3003 Tasman Drive, Santa Clara, California 95054 and with a loan production office
located at 8020 Towers Crescent Drive, Suite 475, Vienna, Virginia 22182, (ii) BLACKBOARD INC., a
Delaware corporation, having an address at 1899 L Street, N.W., Washington, D.C. 20036 (“Company”),
BLACKBOARD ACQUISITION COMPANY, LLC, a Delaware limited liability company having an address at 1899
L Street, N.W., Washington, D.C. 20036 (“Blackboard Acquisition”), BLACKBOARD CAMPUSWIDE, INC., a
Delaware corporation, BLACKBOARD ICOLLEGE, INC., a Delaware corporation having an address at 1899 L
Street, N..W., Washington, D.C. 20036, BLACKBOARD CAMPUSWIDE OF TEXAS, INC., (formerly known as
AT&T Campuswide Access Solutions Of Texas, Inc.), a Texas corporation having an address at 1899 L
Street, N.W., Washington, D.C. 20036, and BB ACQUISITION CORP., a Delaware corporation, having an
address at 1899 L Street, N.W., Washington, D.C. 20036 (each a “Borrower” and collectively, the
“Borrowers”).

RECITALS.

A. The Borrowers and Bank are all parties to that certain Amended and Restated Loan and
Security Agreement dated November 30, 2001, but effective as of October 5, 2001, as amended by that
certain First Amendment to Amended and Restated Loan and Security Agreement dated as of January 11,
2002 among Borrowers and Bank, that certain Second Amendment to Amended and Restated Loan and
Security Agreement dated as of October 4, 2002 among Borrowers and Bank, that certain Third
Amendment to Amended and Restated Loan and Security Agreement dated as of February 17, 2003 among
Borrowers and Bank, that certain Fourth Amendment to Amended and Restated Loan and Security
Agreement dated effective as of May 28, 2003 among Borrowers and Bank, that certain Fifth Amendment
to Amended and Restated Loan and Security Agreement dated as of June 30, 2003 among Borrowers, Bank
and certain affiliates of Borrowers that were made “Borrowers” under the Amended and Restated Loan
and Security Agreement and subsequently removed as “Borrowers” under the Amended and Restated Loan
Documents, that certain Sixth Amendment to Amended and Restated Loan and Security Agreement dated
as of July 25, 2003 among Borrowers and Bank, that certain Seventh Amendment to Amended and
Restated Loan and Security Agreement dated as of April 4, 2004 among Borrowers and Bank, that
certain Eighth Amendment to Amended and Restated Loan and Security Agreement dated as of July 1,
2004 among Borrowers and Bank, and that certain Ninth Amendment to Amended and Restated Loan and
Security Agreement dated as of August 30, 2004 among Borrowers and Bank (as the same may be amended
from time to time, the “Loan Agreement”), pursuant to which Bank has agreed to establish (i) a
revolving line of credit in the maximum principal amount of Eight Million Dollars ($8,000,000) to
be used by Borrowers for working capital needs and general corporate purposes, (ii), an equipment
line of credit in the maximum principal amount of One Million Five Hundred Thousand Dollars
($1,500,000) and (iii) a supplemental equipment line of credit in the maximum principal amount of
Four Million Dollars ($4,000,000) to be used by the Borrowers for the purchase of equipment to be
used by the Borrowers for the purchase of equipment, all as more fully described in the Loan
Agreement.

B. The Borrowers have requested that Bank amend certain provisions of the Loan Agreement and
Bank has agreed on the condition, among others, that Borrowers execute and deliver this Agreement.

C. All capitalized terms used herein and not otherwise defined shall have the meanings given
to such terms in the Loan Agreement.

NOW, THEREFORE, in consideration of the foregoing, and for other good and valuable
consideration, the receipt and sufficiency of which is hereby acknowledged, Borrowers and Bank do
hereby agree as follows:

1. Recitals. The parties hereto acknowledge and agree that the above Recitals are
true and correct in all material respects and that the same are incorporated herein and made a part
hereof by reference.

2. Definitions. From and after the date hereof, the following definitions set forth
in Section 13.1 of the Loan Agreement are hereby amended and restated in their entirety as follows:

“Supplemental Commitment Termination Date” means April 30, 2005.

“Revolving Maturity Date” means April 30, 2005.

3. The Additional Equipment Line. Section 2.4 (c) of the Loan Agreement is amended
and restated in its entirety as follows:

2.4 (c) Subject to the terms and conditions of this Agreement, Bank agrees to lend to
Borrowers, from time to time prior to the Supplemental Commitment Termination Date, equipment
advances (each an “Supplemental Equipment Advance” and collectively the “Supplemental Equipment
Advances”) in an aggregate amount not to exceed the Committed Supplemental Equipment Line. When
repaid, the Supplemental Equipment Advances may not be reborrowed. The proceeds of the
Supplemental Equipment Advances will be used solely to reimburse Borrowers for the purchase of
Eligible Equipment or the purchase or license of Other Equipment (to the extent permitted in this
Agreement), purchased within ninety (90) days of the Supplemental Equipment Advance.
Notwithstanding the foregoing, the initial Supplemental Equipment Advance may be used to reimburse
Borrowers for the purchase of Eligible Equipment or the purchase or license of Other Equipment (to
the extent permitted in this Agreement), purchased at any time after January 1, 2003,
provided such Supplemental Equipment Advance is made no later than forty-five (45) days
after the Supplemental Closing Date and Borrowers provide Bank with accompanying invoices for the
Eligible Equipment or Other Equipment for which reimbursement is being sought. In addition,
notwithstanding the foregoing, the initial Supplemental Equipment Advance made after November 30,
2004 may be used to reimburse Borrowers for the purchase of Eligible Equipment or the purchase or
license of Other Equipment (to the extent permitted in this Agreement), purchased at any time after
February 29, 2004, provided such Supplemental Equipment Advance is made no later than
forty-five (45) days after November 30, 2004 and Borrowers provide Bank with accompanying invoices
for the Eligible Equipment or Other Equipment for which reimbursement is being sought. Bank’s
obligation to lend hereunder shall terminate on the earlier of (i) the occurrence and continuance
of an Event of Default of which the Company has been given notice if required under this Agreement,
or (ii) the Supplemental Commitment Termination Date. For purposes of this Section, the minimum
amount of each Equipment Advance is Twenty Five Thousand Dollars ($25,000) and the maximum number
of Equipment Advances that will be made is eight (8).

4. Facility Fee. Borrowers shall pay to Bank on the date hereof a loan fee on the
Committed Revolving Line in the amount of Eight Thousand Three Hundred Thirty-Three Dollars
($8,333) (the “Committed Revolving Line Fee”). The Committed Revolving Line Fee is considered
earned when paid and is not refundable.

5. Conditions Precedent. This Agreement shall become effective on the date the Bank
receives the following documents, each of which shall be satisfactory in form and substance to the
Bank:

(a) proof that Borrowers have paid all fees, costs and expenses to Bank in connection with
this Agreement, including but not limited to all the Bank’s reasonable attorneys fees and expenses;
and

(b) such other information, instruments, opinions, documents, certificates and reports as the
Bank may deem necessary.

6. Counterparts. This Agreement may be executed in any number of duplicate originals
or counterparts, each of which duplicate original or counterpart shall be deemed to be an original
and all taken together shall constitute one and the same instrument.

7. Loan Documents; Governing Law; Etc. This Agreement is one of the Loan Documents
defined in the Loan Agreement and shall be governed and construed in accordance with the laws of
the Commonwealth of Virginia. The headings and captions in this Agreement are for the convenience
of the parties only and are not a part of this Agreement.

8. Acknowledgments. The Borrowers hereby confirm to the Bank the enforceability and
validity of each of the Loan Documents. In addition, the Borrowers hereby agree that the execution
and delivery of this Agreement and the terms and provisions, covenants or agreements contained in
this Agreement shall not in any manner release, impair, lessen, modify, waive or otherwise limit
the liability and obligations of the Borrowers under the terms of any of the Loan Documents, except
as otherwise specifically set forth in this Agreement. Each Person included in the term “Borrower”
hereby issues, remakes, ratifies and confirms the representations, warranties and covenants
contained in the Loan Documents on and as of the date hereof, both before and after giving effect
to this Agreement except as may be modified by the provisions of this Agreement, and that no Event
of Default or Default has occurred and is continuing or exists or would occur or exist after giving
effect to this Agreement. Nothing in this Agreement shall be deemed to waive any defaults existing
under any of the Loan Documents as of the date hereof.

9. Modifications. This Agreement may not be supplemented, changed, waived,
discharged, terminated, modified or amended, except by written instrument executed by the parties.

10. Consistent Changes. The Loan Documents are hereby amended wherever
necessary to reflect the changes described above.

[SIGNATURES APPEAR ON FOLLOWING PAGE]

1

IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be executed as of the
date first above written.

	 	 	 	 	 
	WITNESS:

	 	SILICON VALLEY BANK
	 	

	 
	 	 	 	 
	/s/ David Steigerwald

	 	By:/s/ Tony Wolfe
	 	(SEAL)
	 

	 	 
	 	

	David Steigerwald

	 	Name: Tony Wolfe

Title: Relationship Manager
	 	

	 
	 	 	 	 
	WITNESS/ATTEST:

	 	BLACKBOARD INC.
	 	

	 
	 	 	 	 
	/s/ Justin Tan

	 	By: /s/ Michael L. Chasen
	 	(SEAL)
	 

	 	 
	 	

	
 
	 	Michael L. Chasen

Chief Executive Officer
	 	

	 
	 	 	 	 
	WITNESS/ATTEST:

	 	BLACKBOARD ACQUISITION

COMPANY, LLC

By:Blackboard Inc., its Member
	 	

	 
	 	 	 	 
	/s/ Justin Tan

	 	By: /s/ Michael L. Chasen
	 	(SEAL)
	 

	 	 
	 	

	
 
	 	Michael L. Chasen

President
	 	

	 
	 	 	 	 
	WITNESS/ATTEST:

	 	BLACKBOARD CAMPUSWIDE, INC.
	 	

	 
	 	 	 	 
	/s/ Justin Tan

	 	By: /s/ Michael L. Chasen
	 	(SEAL)
	 

	 	 
	 	

	
 
	 	Michael L. Chasen

President
	 	

	 
	 	 	 	 
	WITNESS/ATTEST:

	 	BLACKBOARD ICOLLEGE, INC.
	 	

	 
	 	 	 	 
	/s/ Justin Tan

	 	By: /s/ Michael L. Chasen
	 	(SEAL)
	 

	 	 
	 	

	
 
	 	Michael L. Chasen

President
	 	

	 
	 	 	 	 

2

	 	 	 	 	 
	 
	 	 	 	 
	 
	 	 	 	 
	WITNESS/ATTEST:

	 	BLACKBOARD CAMPUSWIDE OF TEXAS, INC.
	 	

	 
	 	 	 	 
	/s/ Justin Tan

	 	By: /s/ Michael L. Chasen
	 	(SEAL)
	 

	 	 
	 	

	
 
	 	Michael L. Chasen

President
	 	

	 
	 	 	 	 
	WITNESS/ATTEST:

	 	BB ACQUISITION CORP.
	 	

	 
	 	 	 	 
	/s/ Justin Tan

	 	By: /s/ Michael L. Chasen
	 	(SEAL)
	 

	 	 
	 	

	
 
	 	Michael L. Chasen

Chief Executive Officer
	 	

	 
	 	 	 	 

3EX-10.2

Blackboard Inc.

Incentive Stock Option Agreement

Granted Under 2004 Stock Incentive Plan

1. Grant of Option.

This agreement evidences the grant by Blackboard Inc., a Delaware corporation (the “Company”),
on [Date], (the “Grant Date”) to [Name], an employee of the Company (the “Participant”), of an
option to purchase, in whole or in part, on the terms provided herein and in the Company’s 2004
Stock Incentive Plan (the “Plan”), a total of [Number] shares (the “Shares”) of common stock, $0.01
par value per share, of the Company (“Common Stock”) at $[Price] per Share. Unless earlier
terminated, this option shall expire at 5:00 p.m., Eastern time, on the tenth anniversary of the
Grant Date (the “Final Exercise Date”).

It is intended that the option evidenced by this agreement shall be an incentive stock option
as defined in Section 422 of the Internal Revenue Code of 1986, as amended, and any regulations
promulgated thereunder (the “Code”). Except as otherwise indicated by the context, the term
“Participant”, as used in this option, shall be deemed to include any person who acquires the right
to exercise this option validly under its terms.

2. Vesting Schedule.

This option will become exercisable (“vest”) as to 25% of the original number of Shares on the
first anniversary of the Vesting Commencement Date and, as to the remaining 75% of the original
number of Shares, ratably on a monthly basis at the end of each of the 36 months following the
first anniversary of the Vesting Commencement Date. The “Vesting Commencement Date” is [Vesting
Commencement Date].

The right of exercise shall be cumulative so that to the extent the option is not exercised in
any period to the maximum extent permissible it shall continue to be exercisable, in whole or in
part, with respect to all Shares for which it is vested until the earlier of the Final Exercise
Date or the termination of this option under Section 3 hereof or the Plan.

3. Exercise of Option.

(a) Form of Exercise. Each election to exercise this option shall be in writing,
signed by the Participant, and received by the Company at its principal office, accompanied by this
agreement, and payment in full in the manner provided in the Plan. The Participant may purchase
less than the number of shares covered hereby, provided that no partial exercise of this option may
be for any fractional share.

(b) Continuous Relationship with the Company Required. Except as otherwise provided
in this Section 3, this option may not be exercised unless the Participant, at the time he or she
exercises this option, is, and has been at all times since the Grant Date, an employee or officer
of, or consultant or advisor to, the Company or any parent or subsidiary of the Company as defined
in Section 424(e) or (f) of the Code (an “Eligible Participant”).

(c) Termination of Relationship with the Company. If the Participant ceases to be an
Eligible Participant for any reason, then, except as provided in paragraphs (d) and (e) below, the
right to exercise this option shall terminate three months after such cessation (but in no event
after the Final Exercise Date), provided that this option shall be exercisable only
to the extent that the Participant was entitled to exercise this option on the date of such
cessation. Notwithstanding the foregoing, if the Participant, prior to the Final Exercise Date,
violates the non-competition or confidentiality provisions of any employment contract,
confidentiality and nondisclosure agreement or other agreement between the Participant and the
Company, the right to exercise this option shall terminate immediately upon such violation.

(d) Exercise Period Upon Death or Disability. If the Participant dies or becomes
disabled (within the meaning of Section 22(e)(3) of the Code) prior to the Final Exercise Date
while he or she is an Eligible Participant and the Company has not terminated such relationship for
“cause” as specified in paragraph (e) below, this option shall be exercisable, within the period of
one year following the date of death or disability of the Participant, by the Participant (or in
the case of death by an authorized transferee), provided that this option shall be
exercisable only to the extent that this option was exercisable by the Participant on the date of
his or her death or disability, and further provided that this option shall not be exercisable
after the Final Exercise Date.

(e) Discharge for Cause. If the Participant, prior to the Final Exercise Date, is
discharged by the Company for “cause” (as defined below), the right to exercise this option shall
terminate immediately upon the effective date of such discharge. “Cause” shall mean willful
misconduct by the Participant or willful failure by the Participant to perform his or her
responsibilities to the Company (including, without limitation, breach by the Participant of any
provision of any employment, consulting, advisory, nondisclosure, non-competition or other similar
agreement between the Participant and the Company), as determined by the Company, which
determination shall be conclusive. The Participant shall be considered to have been discharged for
“Cause” if the Company determines, within 30 days after the Participant’s resignation, that
discharge for cause was warranted.

4. Tax Matters.

(a) Withholding. No Shares will be issued pursuant to the exercise of this option
unless and until the Participant pays to the Company, or makes provision satisfactory to the
Company for payment of, any federal, state or local withholding taxes required by law to be
withheld in respect of this option.

(b) Disqualifying Disposition. If the Participant disposes of Shares acquired upon
exercise of this option within two years from the Grant Date or one year after such Shares were
acquired pursuant to exercise of this option, the Participant shall notify the Company in writing
of such disposition.

5. Nontransferability of Option.

This option may not be sold, assigned, transferred, pledged or otherwise encumbered by the
Participant, either voluntarily or by operation of law, except by will or the laws of descent and
distribution, and, during the lifetime of the Participant, this option shall be exercisable only by
the Participant.

6. Agreement in Connection with Public Offering.

The Participant agrees, in connection with an underwritten public offering of the Company’s
securities pursuant to a registration statement under the Securities Act, (i) not to sell, make
short sale of, loan, grant any options for the purchase of, or otherwise dispose of any shares of
Common Stock held by the Participant (other than those shares included in the offering) without the
prior written consent of the Company or the underwriters managing such initial underwritten public
offering of the Company’s securities for a period of 90 days from the effective date of such
registration statement, and (ii) to execute any agreement reflecting clause (i) above as may be
requested by the Company or the managing underwriters at the time of such offering.

7. Provisions of the Plan.

This option is subject to the provisions of the Plan, a copy of which is furnished to the
Participant with this option.

IN WITNESS WHEREOF, the Company has caused this option to be executed under its corporate seal
by its duly authorized officer. This option shall take effect as a sealed instrument.

Dated: [Grant Date]

	 
	 

	Blackboard Inc.

	 

	By:

	 

	Name:

	 

	Title:

	 

1

PARTICIPANT’S ACCEPTANCE

The undersigned hereby accepts the foregoing option and agrees to the terms and conditions
thereof. The undersigned hereby acknowledges receipt of a copy of the Company’s 2004 Stock
Incentive Plan.

	 
	 

	PARTICIPANT:

	 

	Print Name:

	 

	Address:

	 

	SSN:

	 

2

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