Document:

EX-10.1

EMPLOYMENT AGREEMENT

THIS EMPLOYMENT AGREEMENT (the “Agreement”) is entered into by and between Michael Chasen (“you”)
and Blackboard Inc. (“Blackboard”).

WHEREAS, Blackboard desires to continue to employ you on the terms and conditions hereinafter
set forth and you desire to accept such employment;

NOW, THEREFORE, in consideration of the promises and the mutual agreements contained herein,
the parties agree as follows:

1. Responsibilities. Blackboard agrees to continue to employ you as the Chief Executive
Officer and President. You shall devote your entire business time, attention, skill and energy
exclusively to the business of Blackboard and perform the responsibilities assigned to you in
accordance with the standards and policies that Blackboard may from time to time establish. You
may engage in appropriate civic or charitable activities and devote a reasonable amount of time to
private investments or boards or other activities provided that such activities do not interfere or
conflict with your responsibilities and are not or are not likely to be contrary to Blackboard’s
interests. You and Blackboard agree that your position is essential to Blackboard’s success and
that the highest level of performance is required from you.

2. Term of Employment. Blackboard agrees to employ you, and you agree to remain in
employment with Blackboard, from November 14, 2005 until November 14, 2009 (the “Initial Term”),
unless your employment terminates earlier pursuant to Section 5 below. This Agreement shall
automatically renew for successive one (1) year periods (each, a “Renewal Term” and together with
the Initial Term, the “Term”) unless either party provides prior written notice of its intent not
to renew within thirty (30) days of the applicable Renewal Term.

3. Compensation.

(a) Base Compensation. Your annual base compensation shall initially be US$350,000
(“Base Compensation”), less applicable taxes and withholdings, payable in accordance with
Blackboard’s regular payroll practices from time to time in effect. Blackboard’s Board of
Directors (the “Board”) may review and adjust your Base Compensation periodically.

(b) Bonus Compensation. To be eligible to receive an annual bonus for any year, you
must meet financial performance targets set by the Board and be employed through March
31st of the following year. Your target bonus during the initial year of this Agreement
shall be 70% of your Base Compensation. The actual amount of the bonus, if any, will be determined
by the Board in its sole discretion (the “Bonus”). If a Bonus is awarded, it will be paid in the
year following that for which the Bonus is being awarded. You will receive your Bonus for the
initial year of this Agreement, if any, in fiscal year 2006 for fiscal year 2005.

(c) Business Expenses. During the Term, Blackboard shall pay or reimburse you for all
ordinary and reasonable business-related expenses you incur in the performance of your duties under
this Agreement. Blackboard will reimburse you for all such expenses upon the presentation by you
of an itemized account of such expenditures, together with supporting receipts and other
appropriate documentation.

4. Employee Benefits.

(a) In General. During the Term, you shall be eligible for all employee benefits that
Blackboard may provide to employees who are officers of Blackboard, which may include, but are not
limited to benefits such as health insurance plans, a stock option plan, paid holidays and 401(k),
subject in each case to the generally applicable terms and conditions of any such plan or program
in question and to the determinations of any person or committee administering any such plan or
program. Blackboard reserves the right to modify or terminate any such benefit at any time.

(b) Vacation. You shall be eligible to take paid vacation during each calendar year
in accordance with Blackboard’s Employment Handbook.

5. Termination of Employment. Upon the effective date of termination of your employment
with Blackboard (the “Termination Date”), you will not be eligible for further compensation,
benefits or perquisites under Sections 3 and 4 of this Agreement, other than those that have
already accrued or vested as of the Termination Date. Termination of your employment may occur
under any of the following circumstances:

(a) Expiration of Term. Your employment will terminate if the Term provided for under
Section 2 expires pursuant to the notice requirements of Section 2; or

(b) Termination of Employment by Blackboard. Blackboard has the right to terminate
your employment at any time with or without Cause. For all purposes under this Agreement,
(“Cause”) shall mean:

(i) non-feasance or your material breach of this Agreement, provided that Blackboard first
provides you with written notice of such failure and you fail to cure it within ten (10) days of
such notice;

(ii) an act or omission by you that constitutes gross misconduct, moral turpitude or
fraud;

	 	(iii)	 	a conviction for, or a plea of “guilty” or “no contest” to, a
felony;

(iv) a material breach of any legally recognized duty owed to Blackboard (e.g., your duty of
loyalty and confidentiality); or

(c) Resignation by You. You have the right to resign your employment with Blackboard
at any time, with or without Good Reason, provided that you may resign with Good Reason only if you
provide notice of such reason for resignation to Blackboard stating that such reason will be
grounds for resignation with Good Reason, and if Blackboard fails to cure such reason within thirty
(30) days following receipt of such notice.

(i) For purposes of this Agreement, “Good Reason” shall mean (A) a material failure by
Blackboard to perform its obligations under this Agreement; (B) your relocation outside of your
current residential area without your consent; or (C) a material diminution of your compensation,
duties, or responsibilities at any time or for any reason other than for Cause during the Term of
this Agreement;

(ii) During the Term, you agree to provide Blackboard ninety (90) days’ prior written notice
of your resignation, with or without Good Reason. Blackboard may in its sole discretion place you
on paid administrative leave as of any date prior to the end of such ninety (90) day notice period
and request that you no longer be present on Blackboard premises. During any period of paid
administrative leave, you will not be authorized to act as a representative, or make any statements
on behalf of, Blackboard; or

(d) Death or Disability. Your employment shall be deemed to have been terminated by
you upon your (i) death or (ii) inability to perform your duties under this Agreement, even with
reasonable accommodation, for more than twenty-six (26) weeks, whether or not consecutive, in any
twelve-month period (“Disability”). Termination will be effective upon the occurrence of such
event.

6. Severance Benefits.

(a) If, during the Term of this Agreement, Blackboard terminates your employment without Cause
(as defined in Section 5(b)) or if you terminate your employment with Good Reason (as defined in
Section 5(c)), then Blackboard will pay you $999,999 (“Severance Payment”). The Severance Payment
shall be less applicable taxes and withholdings. To receive the Severance Payment you must sign a
release of any and all claims in the form provided by Blackboard. The Severance Payment shall be
made on one lump sum, unless otherwise agreed by you and Blackboard, at the later of (i) the first
pay period following your Termination Date or (ii) ten (10) days after you deliver the signed
release.

7. Return of Property. Upon termination of your employment with Blackboard for any reason,
you agree to immediately return to Blackboard all equipment, credit cards and other property
belonging to Blackboard. This includes all documents and other information prepared by you or on
your behalf or provided to you in connection with performing your duties for Blackboard, regardless
of the form in which such documents or information are maintained or stored, including computer,
typed, written, imaged, audio, video, micro-fiche, electronic or any other means of recording or
storing documents or other information. You hereby warrant that you will not retain in any form
any such document or other information or copies thereof, except as provided in the following
sentence. You may retain a copy of any documents describing any rights or obligations you may have
after the Termination Date under any employee benefit plan or other agreements.

8. Confidentiality, Non-Solicitation and Non-Competition Agreement.

(a) Confidential Information. You shall not disclose or use at any time, either
during your employment or after your Termination Date, any confidential information, including, but
not limited to, the terms of this Agreement, existing and prospective investments, trade secrets or
proprietary information, strategic sourcing information or analysis, financing information and
sources, patents, patent applications, developmental or experimental work, formulas, test data,
prototypes, models, know how and product specifications, financial information, financial
projections and pro forma financial information, sales and marketing strategies, plans and programs
and product development information, employees’ and consultants’ benefits, perquisites, salaries,
stock options, compensation, formulas or bonuses, and their non-business addresses and telephone
numbers, organizational structure and reporting relationships, business plans, names, addresses,
phone numbers of customers, contracts, including contracts with clients, suppliers, independent
contractors or employees, business plans and forecasts, and existing and prospective projects or
business opportunities (“Confidential Information”) of Blackboard, whether patentable or not, which
you learn as a result of your employment with Blackboard, whether or not you developed such
information. “Confidential Information” shall not include, without limitation, information that is
or later becomes publicly available in a manner wholly unrelated to any breach of this Agreement by
you as of the date it enters the public domain. If you are uncertain whether something is
Confidential Information you should treat it as Confidential Information until you receive
clarification from Blackboard that it is not Confidential Information. Confidential Information
shall remain at all times the property of Blackboard. You may use or disclose Confidential
Information only as authorized and necessary in performing your responsibilities under this
Agreement during your employment with Blackboard; with the General Counsel’s prior written consent;
in a legal proceeding between you and Blackboard to establish the rights of either party under this
Agreement, provided that you stipulate to a protective order to prevent any unnecessary use or
disclosure; or subject to a compulsory legal process that requires disclosure of such information,
provided that you have complied with the following procedures to ensure that Blackboard has an
adequate opportunity to protect its legal interests in preventing disclosure. Upon receipt of a
subpoena that could possibly require disclosure of Confidential Information, you shall provide a
copy of the compulsory process and complete information regarding the circumstances under which you
received it to Blackboard by hand delivery within twenty-four (24) hours. You will not make any
disclosure until the latest possible date for making such disclosure in accordance with the
compulsory process (“Latest Possible Date”). If Blackboard seeks to prevent disclosure in
accordance with the applicable legal procedures, and provides you with notice before the Latest
Possible Date that it has initiated such procedures, you will not make disclosures of any
Confidential Information that is the subject of such procedures, until such objections are
withdrawn or ruled on. You hereby acknowledge that any breach of this Section 8(a) would cause
Blackboard irreparable harm.

(b) Outside Activities. You shall submit to Blackboard’s General Counsel, within a
reasonable time prior to dissemination, the text of any speech, professional paper, article or
similar communication created by you which relates to Blackboard’s present or future business or
research and development endeavors. The General Counsel then will notify you if the dissemination
of the communication is permitted under the terms of this Agreement.

(c) Ownership of Confidential Information; Return of Materials. All Confidential
Information, including without limitation that which is produced by or for Blackboard by you or
anyone else, all materials embodying Confidential Information, and all copies thereof, will remain
the property of Blackboard or of the third party who has furnished it to Blackboard. On your
Termination Date, or at the written request of Blackboard at any time, you will immediately deliver
to Blackboard all materials, and copies thereof, which are in your possession or control and which
contain or are related in any way to any Confidential Information. This includes all documents and
other information prepared by you or on your behalf or provided to you in connection with your
duties while employed by Blackboard, regardless of the form in which such document or information
are maintained or stored, including computer, typed, written, imaged, audio, video, micro-fiche,
electronic or any other means of recording or storing documents or other information. You hereby
warrant that you will not retain in any form any such document or other information or copies
thereof. You may retain a copy of this Agreement and any other document or information describing
any rights you may have after the termination of your employment.

(d) Intellectual Property.

(i) For purposes of this Agreement the following terms will be defined as indicated:

(A) “Inventions” shall mean inventions, ideas, formula, developments, designs, systems,
software, discoveries, and improvements to existing technology, whether or not patentable.

(B) “Improvements” shall mean all inventions, developments, modifications, changes, whether or
not patentable, made to any Inventions and/or Confidential Information.

(C) “Copyrighted Work” shall mean any work of authorship eligible for copyright protection
under the federal and state laws of the United States and foreign countries.

(D) “Copyrights” shall mean any and all rights granted in Copyrighted Works under the laws of
the United States and foreign countries.

(ii) Exclusions. An Invention, Copyright or Copyrighted Work will not be subject to
this Agreement when all the following criteria are met: (A) no equipment, supplies, facilities, or
Confidential Information of Blackboard was used in developing the Invention or Copyrighted Work or
in applying for or obtaining a patent or Copyright; (B) the Invention or Copyrighted Work was
developed entirely on your own time; (C) the Invention or Copyrighted Work does not relate directly
to the business of Blackboard or to Blackboard’s actual or demonstrably anticipated research or
development; and (D) the Invention, Copyright or Copyrighted Work does not result from any work
performed by you for Blackboard or at the request of Blackboard.

(iii) Ownership and Assignment of Rights.

(A) All Inventions, Improvements, or Confidential Information that you have or will conceive
or develop, either alone or with others, shall be the exclusive property of Blackboard. You hereby
assign, and agree to assign, to Blackboard your entire right, title, and interest in and to (I) any
and all such Improvements and Inventions, (II) any and all applications for patent, domestic and
foreign that may be filed on said Improvements and Inventions, and (III) any and all patents that
may issue or be granted on such applications, except those excluded under Section 8(d)(ii) of this
Agreement. Both during and after your Termination Date you will on request immediately sign and
deliver to Blackboard without further consideration any and all documents necessary to perfect the
assignments granted in this Section.

(B) You understand and agree that all Copyrighted Works conceived, developed, created or
contributed to by you shall be considered works made for hire under the copyright laws of the
United States and shall be the exclusive property of Blackboard. Blackboard shall be considered
the author of such Copyrighted Works. You further understand and agree that in the event any
Copyrighted Work created by you within the scope of, or in connection with, your work with
Blackboard, or at the request of Blackboard, fails to meet the legal requirements of a work made
for hire owned by Blackboard, then this Agreement shall operate to assign to Blackboard all of your
rights, title, and interest, including copyrights, in, to and under such Copyrighted Works.
Blackboard shall have sole and absolute discretion to register, enforce, and/or assign Copyrights
for such Copyrighted Works.

(iv) Assistance and Designation of Agent.

(A) Both during and after your Termination Date, you will on request immediately sign and
deliver to Blackboard without further consideration, all instruments in writing requiring your
signature and deemed by Blackboard to be necessary or advisable in, or in connection with, filing
or prosecuting of any application for any patent covering Improvements, Inventions or any
divisional, continuing, renewal or reissue application or reexamination request based upon any
application for patent. In the event that Blackboard is unable for any reason whatsoever to secure
your signature to any lawful and necessary documents required to apply for or execute any patent
application with respect to such idea, process, development, design, system, program, discovery,
invention, improvement or writing (including renewals, extensions, continuations, divisions or
continuations in pat thereof), you hereby irrevocably designate and appoint Blackboard and its
officers and agents, as your agents and attorneys-in-fact to act for and on your behalf and instead
of you, to execute and file any such application and to do all other lawfully permitted acts to
further the prosecution and issuance of patents thereon with the same legal force and effect as if
executed by you.

(B) You will aid Blackboard promptly on request, and without further consideration, in any
matter pertaining to or relating to the protection of any of the Improvements, Inventions,
applications for patents covering Inventions or Improvements, and/or Copyrighted Works. If such
request is made after your employment has ended, Blackboard will reimburse you for any expenses
incurred and compensate for any services rendered in complying with such request at the same rate
at which you were compensated during the final month of your employment.

9. Non-Solicitation/Non-Competition.

During your employment and for one (1) year following your Termination Date (the “Restricted
Period”) you will not, except with prior written approval of Blackboard’s General Counsel, directly
or indirectly, individually or as part of or on behalf of any other person, company, employer or
other entity: (a) hire or attempt to solicit for hire, or encourage to end their relationship with
Blackboard, any persons who have been employed by Blackboard at any time within the previous six
(6) months (a “Covered Employee”); (b) sell or otherwise provide, or solicit for the purposes of
selling or otherwise providing, services or products that are similar or related to those sold by
Blackboard as of the Termination Date to any person or entity that has within the twelve (12)
months preceding the Termination Date purchased any such services or products from Blackboard and
with whom you had direct contact on behalf of Blackboard during that time; or (c) own, manage,
operate, control, be employed by, participate in, work in, advise, consult or contract with, or
support in any manner any business that is similar to the type of business conducted by Blackboard
as of the Termination Date within the geographical area in which, as of the Termination Date,
Blackboard is actively marketing or has made a significant investment in time and money to prepare
to market its products or services within the six (6) month period after the Termination Date. You
agree that these provisions are necessary to protect Blackboard’s legitimate business interests.
You warrant that the provisions will not unreasonably interfere in your ability to earn a living or
to pursue your occupation after the Termination Date. You agree to notify any person or entity to
which you provide services during the Restricted Period of your obligations under this Section 9.

10. Non-Disparagement. You agree to refrain from making any derogatory or defamatory
remarks or comments that may disparage Blackboard, or any officer, employee or agent of Blackboard
during your employment or after your Termination Date.

11. Other Obligations. You warrant that you are not subject to any other obligations
that would conflict with or inhibit your ability to perform your duties under this Agreement. You
represent that you have disclosed to Blackboard the existence and contents of all covenants not to
compete that you have entered into with any other entity. You further warrant that you have not
and will not bring to Blackboard or use in the performance of your responsibilities at Blackboard
any equipment, supplies, facility or trade secret information (that is not generally available to
the public) of any current or former employer or organization other than Blackboard to which you
provided services, unless you have obtained written authorization for their possession and use.

12. Miscellaneous Provisions.

(a) Notices. Unless otherwise provided herein, any notice or other communication
required to be given under the terms of this Agreement must be in writing and must be personally
delivered (i.e., left with an individual 18 years of age or older) or sent by overnight delivery.
Documents sent by overnight delivery will be presumed received on the next business day following
the day sent.

	 	 	 
	If notice is to be sent to Blackboard, it will be sent to:

	 	

	Matthew Small, Esq.

Blackboard Inc

1899 L Street, N.W., 5th Floor

Washington DC 20036

With a copy to:

	 	

	Douglas B. Mishkin, Esq.

	 	If notice is to be sent to you, it will be sent to:
	Patton Boggs, LLP

2550 M Street, NW

Washington, DC 20037

	 	Michael Chasen

8000 Ashboro Court

Chevy Chasen, MD 20815
	 

	 	

(b) Dispute Resolution. You and Blackboard agree that any dispute between you and
Blackboard will be finally resolved by binding arbitration in the District of Columbia in
accordance with the Federal Arbitration Act (“FAA”). You and Blackboard agree to follow the
Dispute Resolution Procedures set forth in Attachment A to this Agreement.

(c) Nature of Agreement. This Agreement and the attachment hereto constitute the
entire agreement between you and Blackboard and supercede all prior agreements and understandings
between you and Blackboard relating to the matters covered by this Agreement, except for the
existing stock option agreements between you and Blackboard, which remain in full force and effect.
Any long-term equity incentives between Blackboard and you shall be contained in a separate
agreement. In making this Agreement, the parties warrant that they did not rely on any
representations or statements other than those contained in this Agreement. No modification of or
amendment to this Agreement will be effective unless in writing and signed by Blackboard’s General
Counsel. A delay or failure by Blackboard to exercise any right that is the subject of this
Agreement will not be construed as a waiver of that right. A waiver of a breach on any one
occasion will not be construed as a waiver of any other breach. Regardless of the choice of law
provisions of the District of Columbia or any other jurisdiction, the parties agree that this
Agreement shall be otherwise interpreted, enforced and governed by the laws of the District of
Columbia. This Agreement will continue in effect until all obligations under it are fulfilled. If
any part of this Agreement is held by a court of competent jurisdiction to be void or
unenforceable, the remaining provisions shall continue with full force and effect. This Agreement
is not assignable by you. This Agreement is binding on you with respect to Blackboard, its
successors or assigns. This Agreement may be executed in any number of counterparts each of which
shall be an original, but all of which together shall constitute one instrument. The headings in
this Agreement are for convenience only and shall not effect the interpretation of this Agreement.
You further certify that you fully understand the terms of this Agreement and have entered into it
knowingly and voluntarily.

IN WITNESS WHEREOF, each of the parties has executed this Agreement, in the case of
Blackboard by its authorized officer, as of the day and year set forth under their signatures
below.

Blackboard Inc.

	 	 	 
	/s/ Michael Chasen

	 	By:/s/ Matthew Small
	 

	 	 
	Michael Chasen

	 	Matthew Small, Senior Vice President

and General Counsel

	 	 	 
	 	 	Date:	 	 	11/14/2005	 	 	Date: 11/14/2005
	 	 	 	 	 	 	 	 	Attachment A

DISPUTE RESOLUTION PROCEDURES

The parties agree to make a good faith effort to informally resolve any dispute before submitting
the dispute to arbitration in accordance with the following procedures:

	 	A.	 	The party claiming to be aggrieved shall furnish to the other a written statement of the
grievance, all persons whose testimony would support the grievance, and the relief requested
or proposed. The written statements must be delivered to the other party within the time
limits for bringing an administrative or court action based on that claim.

	 	B.	 	If the other party does not agree to furnish the relief requested or proposed, or otherwise
does not satisfy the demand of the party claiming to be aggrieved within thirty (30) days and
the aggrieved party wishes to pursue the issue, the aggrieved party shall by written notice
demand that the dispute be submitted to non-binding mediation before a mediator jointly
selected by the parties.

	 	C.	 	If mediation does not produce a resolution of the dispute and either party wishes to pursue
the issue, that party shall request arbitration of the dispute by giving written notice to the
other party within thirty (30) days after mediation. The parties will attempt to agree on a
mutually acceptable arbitrator and, if no agreement is reached, the parties will request a
list of nine arbitrators from the American Arbitration Association and select by alternately
striking names. The arbitration will be conducted consistent with JAMS/Endispute’s rules
governing employment disputes (“Rules”) that are in effect at the time of the arbitration. If
there is any conflict between those Rules and the terms of the Employment Agreement
(“Agreement”), including all attachments thereto, the Agreement will govern. The arbitrator
shall have authority to decide whether the conduct complained of under Subsection (a) above
violates the legal rights of the parties. In any such arbitration proceeding, any hearing
must be transcribed by a certified court reporter and any decision must be supported by
written findings of fact and conclusions of law. The arbitrator’s findings of fact must be
supported by substantial evidence on the record as a whole and the conclusions of law and any
remedy must be provided for by and consistent with the laws of District of Columbia and
federal law. The arbitrator shall have no authority to add to, modify, change or disregard
any lawful term of the Agreement. Blackboard will pay the arbitrator’s fee.

	 	D.	 	Arbitration shall be the exclusive means for final resolution of any dispute between the
parties, except (1) for workers’ compensation and unemployment claims and (2) when injunctive
relief is necessary to preserve the status quo or to prevent irreparable injury, including,
without limitation, any claims concerning an alleged or threatened breach of the
Confidentiality, Non-Solicitation and Non-Competition provisions of your Agreement.
Injunctive relief may be sought from any court of competent jurisdiction located in the
District of Columbia.EX-10.2

EMPLOYMENT AGREEMENT

THIS EMPLOYMENT AGREEMENT (the “Agreement”) is entered into by and between Matthew Pittinsky
(“you”) and Blackboard Inc. (“Blackboard”).

WHEREAS, Blackboard desires to continue to employ you on the terms and conditions hereinafter
set forth and you desire to accept such employment;

NOW, THEREFORE, in consideration of the promises and the mutual agreements contained herein,
the parties agree as follows:

1. Responsibilities. Blackboard agrees to continue to employ you as the Chairman. You
shall devote your entire business time, attention, skill and energy exclusively to the business of
Blackboard and perform the responsibilities assigned to you in accordance with the standards and
policies that Blackboard may from time to time establish. You may engage in appropriate civic or
charitable activities and devote a reasonable amount of time to private investments or boards or
other activities provided that such activities do not interfere or conflict with your
responsibilities and are not or are not likely to be contrary to Blackboard’s interests. You and
Blackboard agree that your position is essential to Blackboard’s success and that the highest level
of performance is required from you. For the avoidance of doubt, this Agreement applies only to
your role as an employee of Blackboard and not to your membership or position on Blackboard’s Board
of Directors (the “Board”).

2. Term of Employment. Blackboard agrees to employ you, and you agree to remain in
employment with Blackboard, from November 14, 2005 until November 14, 2009 (the “Initial Term”),
unless your employment terminates earlier pursuant to Section 5 below. This Agreement shall
automatically renew for successive one (1) year periods (each, a “Renewal Term” and together with
the Initial Term, the “Term”) unless either party provides prior written notice of its intent not
to renew within thirty (30) days of the applicable Renewal Term.

3. Compensation.

(a) Base Compensation. Your annual base compensation shall initially be US$245,000
(“Base Compensation”), less applicable taxes and withholdings, payable in accordance with
Blackboard’s regular payroll practices from time to time in effect. The Boardmay review and adjust
your Base Compensation periodically.

(b) Bonus Compensation. To be eligible to receive an annual bonus for any year, you
must meet financial performance targets set by the Board and be employed through March
31st of the following year. Your target bonus during the initial year of this Agreement
shall be 50% of your Base Compensation. The actual amount of the bonus, if any, will be determined
by the Board in its sole discretion (the “Bonus”). If a Bonus is awarded, it will be paid in the
year following that for which the Bonus is being awarded. You will receive your Bonus for the
initial year of this Agreement, if any, in fiscal year 2006 for fiscal year 2005.

(c) Business Expenses. During the Term, Blackboard shall pay or reimburse you for all
ordinary and reasonable business-related expenses you incur in the performance of your duties under
this Agreement. Blackboard will reimburse you for all such expenses upon the presentation by you
of an itemized account of such expenditures, together with supporting receipts and other
appropriate documentation.

4. Employee Benefits.

(a) In General. During the Term, you shall be eligible for all employee benefits that
Blackboard may provide to employees who are officers of Blackboard, which may include, but are not
limited to benefits such as health insurance plans, a stock option plan, paid holidays and 401(k),
subject in each case to the generally applicable terms and conditions of any such plan or program
in question and to the determinations of any person or committee administering any such plan or
program. Blackboard reserves the right to modify or terminate any such benefit at any time.

(b) Vacation. You shall be eligible to take paid vacation during each calendar year
in accordance with Blackboard’s Employment Handbook.

5. Termination of Employment. Upon the effective date of termination of your employment
with Blackboard (the “Termination Date”), you will not be eligible for further compensation,
benefits or perquisites under Sections 3 and 4 of this Agreement, other than those that have
already accrued or vested as of the Termination Date. Termination of your employment may occur
under any of the following circumstances:

(a) Expiration of Term. Your employment will terminate if the Term provided for under
Section 2 expires pursuant to the notice requirements of Section 2; or

(b) Termination of Employment by Blackboard. Blackboard has the right to terminate
your employment at any time with or without Cause. For all purposes under this Agreement,
(“Cause”) shall mean:

(i) non-feasance or your material breach of this Agreement, provided that Blackboard first
provides you with written notice of such failure and you fail to cure it within ten (10) days of
such notice;

(ii) an act or omission by you that constitutes gross misconduct, moral turpitude or
fraud;

	 	(iii)	 	a conviction for, or a plea of “guilty” or “no contest” to, a
felony;

(iv) a material breach of any legally recognized duty owed to Blackboard (e.g., your duty of
loyalty and confidentiality); or

(c) Resignation by You. You have the right to resign your employment with Blackboard
at any time, with or without Good Reason, provided that you may resign with Good Reason only if you
provide notice of such reason for resignation to Blackboard stating that such reason will be
grounds for resignation with Good Reason, and if Blackboard fails to cure such reason within thirty
(30) days following receipt of such notice.

(i) For purposes of this Agreement, “Good Reason” shall mean (A) a material failure by Blackboard
to perform its obligations under this Agreement; (B) your relocation outside of your current
residential area without your consent; or (C) a material diminution of your compensation or status
at any time or for any reason other than for Cause during the Term of this Agreement.
Notwithstanding the foregoing, you agree that a change of your current role to the position of
Chief Executive Officer, Chief Education Officer, Chief Strategy Officer or Vice-Chairman of
Blackboard shall not be deemed to be a material diminution of your status under Section 5(c)(i)(C).

(ii) During the Term, you agree to provide Blackboard ninety (90) days’ prior written notice
of your resignation, with or without Good Reason. Blackboard may in its sole discretion place you
on paid administrative leave as of any date prior to the end of such ninety (90) day notice period
and request that you no longer be present on Blackboard premises. During any period of paid
administrative leave, you will not be authorized to act as a representative, or make any statements
on behalf of, Blackboard; or

(d) Death or Disability. Your employment shall be deemed to have been terminated by
you upon your (i) death or (ii) inability to perform your duties under this Agreement, even with
reasonable accommodation, for more than twenty-six (26) weeks, whether or not consecutive, in any
twelve-month period (“Disability”). Termination will be effective upon the occurrence of such
event.

6. Severance Benefits.

(a) If, during the Term of this Agreement, Blackboard terminates your employment without Cause
(as defined in Section 5(b)) or if you terminate your employment with Good Reason (as defined in
Section 5(c)), then Blackboard will pay you $750,000 (“Severance Payment”). The Severance Payment
shall be less applicable taxes and withholdings. To receive the Severance Payment you must sign a
release of any and all claims in the form provided by Blackboard. The Severance Payment shall be
made in one lump sum, unless otherwise agreed by you and Blackboard, at the later of (i) the first
pay period following your Termination Date or (ii) ten (10) days after you deliver the signed
release.

7. Return of Property. Upon termination of your employment with Blackboard for any reason,
you agree to immediately return to Blackboard all equipment, credit cards and other property
belonging to Blackboard. This includes all documents and other information prepared by you or on
your behalf or provided to you in connection with performing your duties for Blackboard, regardless
of the form in which such documents or information are maintained or stored, including computer,
typed, written, imaged, audio, video, micro-fiche, electronic or any other means of recording or
storing documents or other information. You hereby warrant that you will not retain in any form
any such document or other information or copies thereof, except as provided in the following
sentence. You may retain a copy of any documents describing any rights or obligations you may have
after the Termination Date under any employee benefit plan or other agreements.

8. Confidentiality, Non-Solicitation and Non-Competition Agreement.

(a) Confidential Information. You shall not disclose or use at any time, either
during your employment or after your Termination Date, any confidential information, including, but
not limited to, the terms of this Agreement, existing and prospective investments, trade secrets or
proprietary information, strategic sourcing information or analysis, financing information and
sources, patents, patent applications, developmental or experimental work, formulas, test data,
prototypes, models, know how and product specifications, financial information, financial
projections and pro forma financial information, sales and marketing strategies, plans and programs
and product development information, employees’ and consultants’ benefits, perquisites, salaries,
stock options, compensation, formulas or bonuses, and their non-business addresses and telephone
numbers, organizational structure and reporting relationships, business plans, names, addresses,
phone numbers of customers, contracts, including contracts with clients, suppliers, independent
contractors or employees, business plans and forecasts, and existing and prospective projects or
business opportunities (“Confidential Information”) of Blackboard, whether patentable or not, which
you learn as a result of your employment with Blackboard, whether or not you developed such
information. “Confidential Information” shall not include, without limitation, information that is
or later becomes publicly available in a manner wholly unrelated to any breach of this Agreement by
you as of the date it enters the public domain. If you are uncertain whether something is
Confidential Information you should treat it as Confidential Information until you receive
clarification from Blackboard that it is not Confidential Information. Confidential Information
shall remain at all times the property of Blackboard. You may use or disclose Confidential
Information only as authorized and necessary in performing your responsibilities under this
Agreement during your employment with Blackboard; with the General Counsel’s prior written consent;
in a legal proceeding between you and Blackboard to establish the rights of either party under this
Agreement, provided that you stipulate to a protective order to prevent any unnecessary use or
disclosure; or subject to a compulsory legal process that requires disclosure of such information,
provided that you have complied with the following procedures to ensure that Blackboard has an
adequate opportunity to protect its legal interests in preventing disclosure. Upon receipt of a
subpoena that could possibly require disclosure of Confidential Information, you shall provide a
copy of the compulsory process and complete information regarding the circumstances under which you
received it to Blackboard by hand delivery within twenty-four (24) hours. You will not make any
disclosure until the latest possible date for making such disclosure in accordance with the
compulsory process (“Latest Possible Date”). If Blackboard seeks to prevent disclosure in
accordance with the applicable legal procedures, and provides you with notice before the Latest
Possible Date that it has initiated such procedures, you will not make disclosures of any
Confidential Information that is the subject of such procedures, until such objections are
withdrawn or ruled on. You hereby acknowledge that any breach of this Section 8(a) would cause
Blackboard irreparable harm.

(b) Outside Activities. You shall submit to Blackboard’s General Counsel, within a
reasonable time prior to dissemination, the text of any speech, professional paper, article or
similar communication created by you which relates to Blackboard’s present or future business or
research and development endeavors. The General Counsel then will notify you if the dissemination
of the communication is permitted under the terms of this Agreement.

(c) Ownership of Confidential Information; Return of Materials. All Confidential
Information, including without limitation that which is produced by or for Blackboard by you or
anyone else, all materials embodying Confidential Information, and all copies thereof, will remain
the property of Blackboard or of the third party who has furnished it to Blackboard. On your
Termination Date, or at the written request of Blackboard at any time, you will immediately deliver
to Blackboard all materials, and copies thereof, which are in your possession or control and which
contain or are related in any way to any Confidential Information. This includes all documents and
other information prepared by you or on your behalf or provided to you in connection with your
duties while employed by Blackboard, regardless of the form in which such document or information
are maintained or stored, including computer, typed, written, imaged, audio, video, micro-fiche,
electronic or any other means of recording or storing documents or other information. You hereby
warrant that you will not retain in any form any such document or other information or copies
thereof. You may retain a copy of this Agreement and any other document or information describing
any rights you may have after the termination of your employment.

(d) Intellectual Property.

(i) For purposes of this Agreement the following terms will be defined as indicated:

(A) “Inventions” shall mean inventions, ideas, formula, developments, designs, systems,
software, discoveries, and improvements to existing technology, whether or not patentable.

(B) “Improvements” shall mean all inventions, developments, modifications, changes, whether or
not patentable, made to any Inventions and/or Confidential Information.

(C) “Copyrighted Work” shall mean any work of authorship eligible for copyright protection
under the federal and state laws of the United States and foreign countries.

(D) “Copyrights” shall mean any and all rights granted in Copyrighted Works under the laws of
the United States and foreign countries.

(ii) Exclusions. An Invention, Copyright or Copyrighted Work will not be subject to
this Agreement when all the following criteria are met: (A) no equipment, supplies, facilities, or
Confidential Information of Blackboard was used in developing the Invention or Copyrighted Work or
in applying for or obtaining a patent or Copyright; (B) the Invention or Copyrighted Work was
developed entirely on your own time; (C) the Invention or Copyrighted Work does not relate directly
to the business of Blackboard or to Blackboard’s actual or demonstrably anticipated research or
development; and (D) the Invention, Copyright or Copyrighted Work does not result from any work
performed by you for Blackboard or at the request of Blackboard.

(iii) Ownership and Assignment of Rights.

(A) All Inventions, Improvements, or Confidential Information that you have or will conceive
or develop, either alone or with others, shall be the exclusive property of Blackboard. You hereby
assign, and agree to assign, to Blackboard your entire right, title, and interest in and to (I) any
and all such Improvements and Inventions, (II) any and all applications for patent, domestic and
foreign that may be filed on said Improvements and Inventions, and (III) any and all patents that
may issue or be granted on such applications, except those excluded under Section 8(d)(ii) of this
Agreement. Both during and after your Termination Date you will on request immediately sign and
deliver to Blackboard without further consideration any and all documents necessary to perfect the
assignments granted in this Section.

(B) You understand and agree that all Copyrighted Works conceived, developed, created or
contributed to by you shall be considered works made for hire under the copyright laws of the
United States and shall be the exclusive property of Blackboard. Blackboard shall be considered
the author of such Copyrighted Works. You further understand and agree that in the event any
Copyrighted Work created by you within the scope of, or in connection with, your work with
Blackboard, or at the request of Blackboard, fails to meet the legal requirements of a work made
for hire owned by Blackboard, then this Agreement shall operate to assign to Blackboard all of your
rights, title, and interest, including copyrights, in, to and under such Copyrighted Works.
Blackboard shall have sole and absolute discretion to register, enforce, and/or assign Copyrights
for such Copyrighted Works.

(iv) Assistance and Designation of Agent.

(A) Both during and after your Termination Date, you will on request immediately sign and
deliver to Blackboard without further consideration, all instruments in writing requiring your
signature and deemed by Blackboard to be necessary or advisable in, or in connection with, filing
or prosecuting of any application for any patent covering Improvements, Inventions or any
divisional, continuing, renewal or reissue application or reexamination request based upon any
application for patent. In the event that Blackboard is unable for any reason whatsoever to secure
your signature to any lawful and necessary documents required to apply for or execute any patent
application with respect to such idea, process, development, design, system, program, discovery,
invention, improvement or writing (including renewals, extensions, continuations, divisions or
continuations in pat thereof), you hereby irrevocably designate and appoint Blackboard and its
officers and agents, as your agents and attorneys-in-fact to act for and on your behalf and instead
of you, to execute and file any such application and to do all other lawfully permitted acts to
further the prosecution and issuance of patents thereon with the same legal force and effect as if
executed by you.

(B) You will aid Blackboard promptly on request, and without further consideration, in any
matter pertaining to or relating to the protection of any of the Improvements, Inventions,
applications for patents covering Inventions or Improvements, and/or Copyrighted Works. If such
request is made after your employment has ended, Blackboard will reimburse you for any expenses
incurred and compensate for any services rendered in complying with such request at the same rate
at which you were compensated during the final month of your employment.

9. Non-Solicitation/Non-Competition.

During your employment and for one (1) year following your Termination Date (the “Restricted
Period”) you will not, except with prior written approval of Blackboard’s General Counsel, directly
or indirectly, individually or as part of or on behalf of any other person, company, employer or
other entity: (a) hire or attempt to solicit for hire, or encourage to end their relationship with
Blackboard, any persons who have been employed by Blackboard at any time within the previous six
(6) months (a “Covered Employee”); (b) sell or otherwise provide, or solicit for the purposes of
selling or otherwise providing, services or products that are similar or related to those sold by
Blackboard as of the Termination Date to any person or entity that has within the twelve (12)
months preceding the Termination Date purchased any such services or products from Blackboard and
with whom you had direct contact on behalf of Blackboard during that time; or (c) own, manage,
operate, control, be employed by, participate in, work in, advise, consult or contract with, or
support in any manner any business that is similar to the type of business conducted by Blackboard
as of the Termination Date within the geographical area in which, as of the Termination Date,
Blackboard is actively marketing or has made a significant investment in time and money to prepare
to market its products or services within the six (6) month period after the Termination Date. You
agree that these provisions are necessary to protect Blackboard’s legitimate business interests.
You warrant that the provisions will not unreasonably interfere in your ability to earn a living or
to pursue your occupation after the Termination Date. You agree to notify any person or entity to
which you provide services during the Restricted Period of your obligations under this Section 9.

10. Non-Disparagement. You agree to refrain from making any derogatory or defamatory
remarks or comments that may disparage Blackboard, or any officer, employee or agent of Blackboard
during your employment or after your Termination Date.

11. Other Obligations. You warrant that you are not subject to any other obligations
that would conflict with or inhibit your ability to perform your duties under this Agreement. You
represent that you have disclosed to Blackboard the existence and contents of all covenants not to
compete that you have entered into with any other entity. You further warrant that you have not
and will not bring to Blackboard or use in the performance of your responsibilities at Blackboard
any equipment, supplies, facility or trade secret information (that is not generally available to
the public) of any current or former employer or organization other than Blackboard to which you
provided services, unless you have obtained written authorization for their possession and use.

12. Miscellaneous Provisions.

(a) Notices. Unless otherwise provided herein, any notice or other communication
required to be given under the terms of this Agreement must be in writing and must be personally
delivered (i.e., left with an individual 18 years of age or older) or sent by overnight delivery.
Documents sent by overnight delivery will be presumed received on the next business day following
the day sent.

	 	 	 
	If notice is to be sent to Blackboard, it will be sent to:

	 	

	Matthew Small, Esq.

Blackboard Inc

1899 L Street, N.W., 5th Floor

Washington DC 20036

With a copy to:

	 	

	Douglas B. Mishkin, Esq.

	 	If notice is to be sent to you, it will be sent to:
	Patton Boggs, LLP

2550 M Street, NW

Washington, DC 20037

	 	Matthew Pittinsky

164 W. 79th Street, Apartment 8d

New York, NY 10024
	 

	 	

(b) Dispute Resolution. You and Blackboard agree that any dispute between you and
Blackboard will be finally resolved by binding arbitration in the District of Columbia in
accordance with the Federal Arbitration Act (“FAA”). You and Blackboard agree to follow the
Dispute Resolution Procedures set forth in Attachment A to this Agreement.

(c) Nature of Agreement. This Agreement and the attachment hereto constitute the
entire agreement between you and Blackboard and supercede all prior agreements and understandings
between you and Blackboard relating to the matters covered by this Agreement, except for the
existing stock option agreements between you and Blackboard, which remain in full force and effect.
Any long-term equity incentives between Blackboard and you shall be contained in a separate
agreement. In making this Agreement, the parties warrant that they did not rely on any
representations or statements other than those contained in this Agreement. No modification of or
amendment to this Agreement will be effective unless in writing and signed by Blackboard’s General
Counsel. A delay or failure by Blackboard to exercise any right that is the subject of this
Agreement will not be construed as a waiver of that right. A waiver of a breach on any one
occasion will not be construed as a waiver of any other breach. Regardless of the choice of law
provisions of the District of Columbia or any other jurisdiction, the parties agree that this
Agreement shall be otherwise interpreted, enforced and governed by the laws of the District of
Columbia. This Agreement will continue in effect until all obligations under it are fulfilled. If
any part of this Agreement is held by a court of competent jurisdiction to be void or
unenforceable, the remaining provisions shall continue with full force and effect. This Agreement
is not assignable by you. This Agreement is binding on you with respect to Blackboard, its
successors or assigns. This Agreement may be executed in any number of counterparts each of which
shall be an original, but all of which together shall constitute one instrument. The headings in
this Agreement are for convenience only and shall not effect the interpretation of this Agreement.
You further certify that you fully understand the terms of this Agreement and have entered into it
knowingly and voluntarily.

IN WITNESS WHEREOF, each of the parties has executed this Agreement, in the case of
Blackboard by its authorized officer, as of the day and year set forth under their signatures
below.

Blackboard Inc.

	 	 	 
	/s/ Matthew Pittinsky

	 	By:/s/ Matthew Small
	 

	 	 
	Matthew Pittinsky

	 	Matthew Small, Senior Vice President

and General Counsel

	 	 	 
	 	 	Date:	 	 	11/14/2005	 	 	Date: 11/14/2005
	 	 	 	 	 	 	 	 	Attachment A

DISPUTE RESOLUTION PROCEDURES

The parties agree to make a good faith effort to informally resolve any dispute before submitting
the dispute to arbitration in accordance with the following procedures:

	 	A.	 	The party claiming to be aggrieved shall furnish to the other a written statement of the
grievance, all persons whose testimony would support the grievance, and the relief requested
or proposed. The written statements must be delivered to the other party within the time
limits for bringing an administrative or court action based on that claim.

	 	B.	 	If the other party does not agree to furnish the relief requested or proposed, or otherwise
does not satisfy the demand of the party claiming to be aggrieved within thirty (30) days and
the aggrieved party wishes to pursue the issue, the aggrieved party shall by written notice
demand that the dispute be submitted to non-binding mediation before a mediator jointly
selected by the parties.

	 	C.	 	If mediation does not produce a resolution of the dispute and either party wishes to pursue
the issue, that party shall request arbitration of the dispute by giving written notice to the
other party within thirty (30) days after mediation. The parties will attempt to agree on a
mutually acceptable arbitrator and, if no agreement is reached, the parties will request a
list of nine arbitrators from the American Arbitration Association and select by alternately
striking names. The arbitration will be conducted consistent with JAMS/Endispute’s rules
governing employment disputes (“Rules”) that are in effect at the time of the arbitration. If
there is any conflict between those Rules and the terms of the Employment Agreement
(“Agreement”), including all attachments thereto, the Agreement will govern. The arbitrator
shall have authority to decide whether the conduct complained of under Subsection (a) above
violates the legal rights of the parties. In any such arbitration proceeding, any hearing
must be transcribed by a certified court reporter and any decision must be supported by
written findings of fact and conclusions of law. The arbitrator’s findings of fact must be
supported by substantial evidence on the record as a whole and the conclusions of law and any
remedy must be provided for by and consistent with the laws of District of Columbia and
federal law. The arbitrator shall have no authority to add to, modify, change or disregard
any lawful term of the Agreement. Blackboard will pay the arbitrator’s fee.

	 	D.	 	Arbitration shall be the exclusive means for final resolution of any dispute between the
parties, except (1) for workers’ compensation and unemployment claims and (2) when injunctive
relief is necessary to preserve the status quo or to prevent irreparable injury, including,
without limitation, any claims concerning an alleged or threatened breach of the
Confidentiality, Non-Solicitation and Non-Competition provisions of your Agreement.
Injunctive relief may be sought from any court of competent jurisdiction located in the
District of Columbia.

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