Document:

exv10w1

 

Exhibit 10.1

February 22, 2007

D. Michael Keenan

1135 Bellview Road

McLean, VA 22102

      Re:     Separation Agreement

Dear Mr. Keenan:

     This letter (“Separation Agreement”) sets forth our understanding with respect to the
termination of your service as Chief Executive Officer of Global Telecom & Technology, Inc. (the
“Company”) and in any other offices and positions you hold as an employee with respect to the
Company and any of its affiliated entities and subsidiaries pursuant to the Employment Agreement
dated October 15, 2006 between you and the Company (the “Employment Agreement”). Your last day of
employment shall be February 23, 2007 (the “Separation Date”). We have also agreed that you will
remain as a director of the Company (subject to shareholder approval requirements) until such time
as your direct ownership interest in the Company represents less than five percent (5%) of the
outstanding shares of common stock of the Company (excluding warrants and stock options), following
which time you agree to resign from the Company’s Board of Directors immediately upon request from
the Chairman.

Separation Payments and Benefits

     We have both agreed that you will receive payment of your base salary, plus any earned but
unused vacation, through the Separation Date. In addition, the Company will, consistent with its
normal payroll cycle and benefit administration processes as applicable to its employees, continue
to pay your salary and make health benefits available to you for a period of twelve (12) months
from the Separation Date (“Severance Period”). At the conclusion of the Severance Period, you will
be eligible to continue your health coverage pursuant to COBRA, and you will be provided with
notice about your rights under COBRA at that time. You will also receive a bonus payment in cash
equal to $166,667, payable upon the earlier of the expiration of the Severance Period or such time
as the Company awards bonuses to its executives with respect to its 2007 fiscal year. Finally, we
have agreed that your grant of restricted stock as contemplated in the Employment Agreement shall
vest in full at the same time as the bonus is paid pursuant to the preceding sentence (but in any
event shall vest no later than the last day of the Severance Period) in lieu of the vesting
schedules set forth in Section 5.4 of the Employment Agreement and in the associated restricted
stock agreement. The Company may withhold from any amounts payable under this Separation Agreement
such federal, state, local or foreign taxes as shall be required to be withheld pursuant to any
applicable law or regulation.

 

 

Waivers and Releases

     By our mutual signatures below, we have agreed that: (i) the Company will have no further
obligations under the Employment Agreement to make payments of money in the form of salary, bonus,
or otherwise, benefit contributions, transfers of stock or other things of value (including, but
not limited to, perquisites) except as provided in this Separation Agreement; and (ii) the Company
shall have no liability with respect to termination of your employment except as expressly set
forth herein.

     In exchange for the payments and benefits set forth herein, you hereby release, acquit and
forever discharge the Company and its subsidiaries and affiliates, and each of their respective
officers, directors, associates, agents, employees, attorneys, shareholders, successors, assigns
and affiliates, past present and future, of and from any and all claims, liabilities, demands,
causes of action, costs, expenses, attorneys’ fees, damages, indemnities and obligations of every
kind and nature, in law, equity, or otherwise, known and unknown, suspected and unsuspected,
disclosed and undisclosed, arising out of or in any way related to your employment (including
termination thereof) at any time up to and including the Separation Date.

     Without limitation of the foregoing releases, you acknowledge that you knowingly and
voluntarily waive and release any rights you may have under the federal Age Discrimination in
Employment Act of 1967, as amended (“ADEA”), and that the consideration given for the waiver and
releases herein is in addition to anything of value to which you were already entitled. You further
acknowledge that you have been advised by this writing, as required by the ADEA, that: (a) your
waiver and release do not apply to any rights or claims that may arise after the date you sign this
Separation Agreement; (b) you should consult with an attorney prior to signing this Separation
Agreement (although you may choose voluntarily not to do so); (c) you have twenty-one (21) days to
consider this Separation Agreement (although you may choose voluntarily to execute this Separation
Agreement earlier); (d) you have seven (7) days following the date you sign this Separation
Agreement to revoke the Separation Agreement by providing written notice of such revocation to the
Company’s General Counsel; and (e) this Separation Agreement will not be effective until the date
upon which the revocation period has expired, which will be the eighth day after this Separation
Agreement is signed by you.

     Notwithstanding the foregoing, this release of claims does not include a release of any claims
you may have for workers’ compensation or unemployment insurance benefits, for claims arising out
of the Stock Purchase Agreement, dated May 23, 2006, as amended, the two Promissory Notes each
dated October 15, 2006, the two Escrow Agreements each dated October 15, 2006, or for the Company’s
failure to comply with this Separation Agreement.

     To the Company’s actual knowledge, based upon facts known to it as of the Separation Date
without further inquiry or investigation, there is no claim arising since October 15, 2006 through
the Separation Date with respect to your employment by the Company. Nothing in the preceding
sentence shall be construed to waive any rights the Company may have with respect to claims
relating to or arising out of the Stock Purchase Agreement, dated May 23, 2006, as amended, or any
failure on your part to comply with this Separation Agreement.

 

 

Cooperation and Post-Employment Obligations

     Until March 31, 2007, the Company will retain the files existing as of the Separation Date on
your computer and your laptop, as well as the files and records existing in your voice-mail and
e-mail accounts as of the Separation Date. During that period of time, the Company will provide
you with reasonable access to the computer, laptop, and voicemail and e-mail accounts to review and
make hard copies or electronic copies of personal files, documents, and e-mail, including, for
example, copies of the Stock Purchase Agreement and related documents, documents related to your
compensation and benefits during your employment with the Company, and Outlook contacts. Such
access shall be provided on the Company’s premises during normal business hours, and the Company
shall be entitled to review all copies that you wish to remove from the premises prior to such
removal. The Company will arrange to permit you to receive voicemail and review e-mails that come
in after the Separation Date for a reasonable period of time, not to be less than a period of two
weeks.

     You agree to cooperate fully, at the Company’s request, to promptly sign and execute all
documents and to do all such deeds, acts and things as the Company may reasonably request, which
may be necessary or appropriate to effectuate the termination of your employment and affiliation
with the Company and its affiliated entities. The Company agrees that it is responsible for
drafting for your review any public filings necessitated by the termination of your employment with
the Company. The Company will indemnify you for all actions within the authorized course and scope
of your employment with the Company (for the length of your employment with the Company) to the
extent permitted by the Company’s by-laws as in effect on the signing of this Separation Agreement.
The Company shall take no actions to remove you from coverage under the Company’s directors’ and
officers’ liability insurance policy as in effect on the Separation Date. You shall continue to be
covered under such policy and any replacement policy to the extent the terms of such policies cover
former officers and directors. You agree not to defame or disparage the Company, its affiliates,
its shareholders, directors, officers, employees, or business or employment practices at any time.
Notwithstanding the foregoing, you will respond accurately and fully to any question, inquiry or
request for information when required by legal process. The Company agrees to instruct its Board
of Directors and officers not to defame or disparage you at any time. You will have final approval
of the Press Release that is issued by the Company regarding the termination of your employment.

     We both further hereby agree and reaffirm our mutual intent to be bound, as applicable, by all
terms and conditions of the Employment Agreement following its termination (including, but not
limited to, the Executive Assignment of Inventions and Confidentiality Agreement) pursuant to
Section 7.8 of the Employment Agreement.

Miscellaneous

     This Separation Agreement constitutes the complete, final and exclusive embodiment of the
entire agreement between you and the Company with regard to the termination of your employment. It
is entered into without reliance on any promise or representation, written or oral, other than
those expressly contained herein, and it supersedes any other such promises, warranties or
representations. You agree that neither this Separation Agreement nor performance

 

 

hereunder constitutes an admission by the Company of any violation of any federal, state or local
law, regulation, common law, of any breach of any contract or any other wrongdoing of any type.
This Separation Agreement may not be modified or amended except in a writing signed by both you and
the Company’s Executive Chairman or Chief Executive Officer at that time. This Separation Agreement
shall bind the heirs, personal representatives, successors and assigns of both you and the Company,
and inure to the benefit of both you and the Company, their heirs, successors and assigns. If any
provision of this Separation Agreement is determined to be invalid or unenforceable, in whole or in
part, this determination will not affect any other provision of this Separation Agreement and the
provision in question shall be modified by the court so as to be rendered enforceable in a manner
consistent with the intent of the parties insofar as possible.

     This Separation Agreement shall be deemed to have been entered into and shall be construed and
enforced in accordance with the laws of the State of Delaware, without giving effect to the
principles of conflicts of laws. Any ambiguity in this Separation Agreement shall not be construed
against either party as the drafter. Any waiver of a breach of this Separation Agreement shall be
in writing and shall not be deemed to be a waiver of any successive breach.

     If this Separation Agreement is acceptable to you, please sign below and return the original
to me as promptly as possible, but in any event no later than twenty-one (21) days after you
receive this document. We thank you for your attention to this correspondence, and we wish you the
best in your future endeavors.

	 	 	 	 	 
	 	Sincerely,

 	 
	 	/s/ H. Brian Thompson
 	 
	 	H. Brian Thompson 	 
	 	Executive Chairman 	 
	 

BY SIGNING THIS SEPARATION AGREEMENT BELOW, I ACKNOWLEDGE THAT I HAVE CAREFULLY READ AND FULLY
UNDERSTAND ALL OF THE PROVISIONS OF THIS SEPARATION AGREEMENT AND VOLUNTARILY ENTER INTO THIS
SEPARATION AGREEMENT.

	 	 	 	 	 
	AGREED AND ACCEPTED:

 	 
	/s/ D. Michael Keenan
 	 
	D. Michael Keenanexv10w7

 

Exhibit 10.7

EMPLOYMENT AGREEMENT

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

     WHEREAS, Blackboard desires 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 hire you as the Senior Vice President, Sales.
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. With prior written notice to Blackboard,
you may engage in appropriate civic or charitable activities during business hours 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 the date hereof until June 3, 2006 (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 ninety (90) days of the applicable Renewal Term.

3. Compensation.

     (a) Base Compensation. Your annual base compensation shall initially be US$225,000
(“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, and to be eligible to receive a quarterly bonus for any
quarter, you must remain employed for at least thirty one (31) days following the end of such
quarter. Your initial on-target bonus will be 100% of your Base Compensation. The actual amount
of the bonus, if any, will be determined by the Board in its sole discretion. If an annual bonus
is awarded, it will be paid in the year following that for which the bonus is being awarded, and if
a quarterly bonus is awarded, it will be paid in the quarter following that for which the bonus is
being awarded.

     (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.

     (d) Relocation Expenses. Blackboard will provide you with temporary housing and
reimbursement for reasonable travel expenses for necessary travel between Concord, Massachusetts
and Washington DC for a period of up to three (3) months; provided, however, that such three (3)
month period may be extended by Blackboard on a month-to-month basis for up to an additional three
(3) months. In addition, for your relocation to the metropolitan D.C. area, Blackboard will
arrange for (i) the reasonable shipment of your household goods to the metropolitan D.C. area at
Blackboard’s expense and (ii) reimbursement of up to $25,000 in other documented reasonable
relocation expenses. To receive reimbursement, you must submit to Blackboard receipts documenting
the expenses incurred.

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) a failure by you to substantially perform your duties under this Agreement or your job
responsibilities, other than a failure resulting from your complete or partial incapacity due to
physical or mental illness or impairment;

          (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; or

          (iv) a material breach of any duty owed to Blackboard, including but not limited to the duties
of loyalty and confidentiality.

     (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 the your
current residential area without your consent; or (C) a material diminution of your compensation,
duties or responsibilities.

          (ii) During the Term, you agree to provide Blackboard six (6) months’ 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 6-month 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 Payments.

     (a) After the first six (6) months of your Initial Term have elapsed, if during the remainder
of the Term Blackboard terminates your employment without Cause (as defined in Section 5(b)) or
fails to renew this Agreement pursuant to Section 2, then Blackboard will pay you your then current
Base Salary, less applicable taxes and withholdings, and COBRA premiums for the six (6) months
immediately following the Termination Date (“Severance Payments”). The Severance Payments shall be
made consistent with Blackboard’s regular payroll schedule. To

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receive the Severance Payments you must sign a release of any and all claims in the form
provided by Blackboard. Such Severance Payments shall begin at the later of (i) the first pay
period following your Termination Date or (ii) ten (10) days after you deliver the signed release
to Blackboard. The Severance Payments will end the earlier of (A) six (6) months after they begin
or (B) upon your employment in a position with no less seniority and compensation, including as an
employee, owner or independent contractor. You have a duty to take all reasonable measures to find
employment promptly after your employment with Blackboard terminates.

     (b) If during the Term you resign for Good Reason, as defined in Section 5(c), you shall be
entitled to the Severance Payment as described in Section 6(a), provided that you continue working
for Blackboard for a period of at least six (6) months following Blackboard’s receipt of written
notice from you of your resignation pursuant to Section 5(c)(i)(A), unless you are placed on
administrative leave by Blackboard; in such case, you shall be entitled to six (6) months’
severance under this Section 6 as well as regular compensation under Section 3 until the
Termination Date. To receive the Severance Payment, you must sign a release of any and all claims
in the form provided by Blackboard. Such Severance Payment shall begin at the later of (i) the
first pay period following your Termination Date or (ii) ten (10) days after you deliver the signed
release to Blackboard. The Severance Payments will end the earlier of (A) six (6) months after
they begin or (B) upon your employment in any capacity, including as an employee, owner or
independent contractor. You have a duty to take all reasonable measures to find employment
promptly after your employment with Blackboard terminates.

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 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

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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 external 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. Notwithstanding the foregoing,
you shall have sole ownership to Copyright or Copyright Work developed by you if advance written
permission was obtained from Blackboard’s General Counsel to develop such material.

          (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

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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”). If during the Restricted Period any Covered Employee accepts
employment with any person, company, employer or other entity of which you are an officer,
director, employee, partner, shareholder (other than of less than 5% of the stock in a publicly
traded company) or joint venture, it will be presumed that the Covered Employee was hired in
violation of this provision (the “Presumption”). This Presumption may only be overcome by your
showing by a preponderance of the evidence that you were not directly or indirectly involved in
hiring, soliciting or encouraging the Covered Employee to leave employment with Blackboard; (b)
sell or otherwise provide, or solicit for the purposes of selling or otherwise providing, services
or products that directly or indirectly compete with 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

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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 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.

     (b) Dispute Resolution. You and Blackboard agree that any dispute between you and
Blackboard will be finally resolved by binding arbitration 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. 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 the Senior Vice President for Human Resources of
Blackboard. 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/ David Sample

	 	 	 	By:
	 	/s/ Michael Chasen
	 

	 	 	 	 	 	 
	David Sample

	 	 	 	 	 	Michael Chasen, CEO and President
	 
	 	 	 	 	 	 
	Date: June 3, 2005	 	Date: June 3, 2005

-6-

 

AMENDMENT TO EMPLOYMENT AGREEMENT

Blackboard Inc. (“Blackboard”) and David Sample hereby enter into this Amendment to the June 3,
2005 Employment Agreement (“Agreement”) between them.

The parties, for good and valuable consideration, the sufficiency of which is hereby acknowledged,
hereby agree as follows:

1. The first sentence of Section 3(d) of the Agreement is hereby amended and restated as follows:

“(d) Relocation Expenses. (i) Blackboard will provide you with temporary housing
and reimbursement for reasonable travel expenses for necessary travel between Concord,
Massachusetts and Washington DC until April 30, 2006 as follows: Blackboard will (i)
directly pay for your temporary housing from July 5, 2005 to October 5, 2005 in the amount
of $11,453.89 and will withhold the appropriate taxes for such amount, and (ii) reimburse
you for your temporary housing from October 5, 2005 to April 30, 2005 in the amount of
$2,166 per month and will gross up such amounts for the applicable tax.”

2. Except as expressly provided herein, the terms and conditions of the Agreement remain
unmodified. All capitalized terms not defined herein shall have the meaning set forth in the
Agreement. This Amendment shall be governed by laws of the District of Columbia and shall be
subject to the Dispute Resolution provisions set forth in Section 12 of the Agreement. If any part
of this Amendment is held by a court of competent jurisdiction to be void or unenforceable, the
remaining provisions shall continue with full force and effect.

This Amendment has been agreed to and executed by the following parties on the dates set forth
opposite their names:

	 	 	 	 	 	 	 
	 	 	 	 	Blackboard Inc.
	 
	 	 	 	 	 	 
	/s/ David Sample

	 	 	 	By:
	 	/s/ Michael Chasen
	 

	 	 	 	 	 	 
	David Sample

	 	 	 	 	 	Michael Chasen, CEO and President
	 
	 	 	 	 	 	 
	January 31, 2006	 	 	 	January 31, 2006

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