SECOND AMENDED AND RESTATED INVESTORS' RIGHTS AGREEMENT

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Exhibit 10.1

Execution Copy

TECHTARGET, INC.

SECOND AMENDED AND RESTATED INVESTORS' RIGHTS AGREEMENT

        This Second Amended and Restated Investors' Rights Agreement is entered into as of the 17th day of December, 2004, by and among TechTarget, Inc., a Delaware corporation (the " Company "), the persons and entities listed on Exhibit A hereto under the heading "Investors" (individually, an " Investor ", and, collectively, the " Investors ") and, for the purposes of Articles II and V only, SG Cowen Securities Corporation, a New York corporation (" SG Cowen ").

Recitals

        WHEREAS, the Company and certain of the Investors are parties to an Amended and Restated Investors' Rights Agreement dated as of May 21, 2004 (the " Existing Agreement ");

        WHEREAS, certain Investors have on this date acquired shares of the Company's Series C Convertible Preferred Stock, $.001 par value per share (the " Series C Preferred Stock "), pursuant to a Series C Convertible Preferred Stock Purchase Agreement (the " Purchase Agreement ");

        WHEREAS, the execution of this Agreement is a condition to the Investors' acquisition of the shares of Series C Preferred Stock; and

        WHEREAS, the Company desires to grant to the Investors registration rights and certain other rights on the terms and conditions hereinafter set forth by amending and restating in its entirety the Existing Agreement.

        NOW, THEREFORE, in consideration of the mutual promises and covenants contained in this Agreement, and for other valuable consideration, receipt of which is hereby acknowledged, the parties hereto agree that the Existing Agreement be amended and restated in its entirety as follows:

ARTICLE I. DEFINITIONS

        As used in this Agreement, the following terms shall have the following respective meanings:

        " Commission " means the United States Securities and Exchange Commission, or any other federal agency at the time administering the Securities Act.

        " Common Stock " means the common stock, $0.001 par value per share, of the Company.

        " Exchange Act " means the Securities Exchange Act of 1934, as amended, or any similar federal statute, and the rules and regulations of the Commission issued under such Act, as they each may, from time to time, be in effect.

        " Initial Public Offering " means the sale of shares of Common Stock in a firm commitment underwritten public offering pursuant to a Registration Statement at a price to the public per share of at least $4.44 (subject to appropriate adjustment for stock splits, stock dividends, reclassifications, recapitalizations and other similar events affecting such shares).

         " Registration Statement " means a registration statement filed by the Company with the Commission for a public offering and sale of Common Stock by the Company (other than a registration statement on Form S-8 or Form S-4, or their successors, or any other form for a similar limited purpose, or any registration statement covering only securities proposed to be issued in exchange for securities or assets of another corporation).

        " Registration Expenses " means the expenses described in Section 2.4 below.

        " Registrable Shares " means (i) the shares of Common Stock issued or issuable upon conversion of the Shares, (ii) any shares of Common Stock, and any shares of Common Stock issued or issuable upon the conversion or exercise of any other securities, acquired by the Investors, (iii) any other shares of Common Stock issued in respect of such shares (because of stock splits, stock dividends, reclassifications, recapitalizations, or similar events) and (iv) shares of Common Stock issued or issuable upon exercise of SG Cowen Warrants; provided, however, that shares of Common Stock which are Registrable Shares shall cease to be Registrable Shares (a) upon any sale of such shares pursuant to a Registration Statement or Rule 144 under the Securities Act, (b) upon any sale of such shares in any manner to a person or entity which, by virtue of Section 5.2 of this Agreement, is not entitled to the rights provided by this Agreement, or (c) at such time as they become eligible for resale pursuant to Rule 144(k) under the Securities Act. Wherever reference is made in this Agreement to a request or consent of holders of a certain percentage of Registrable Shares, the determination of such percentage shall include the shares of Common Stock issuable upon conversion of the Shares even if such conversion has not yet been effected.

        " Securities Act " means the Securities Act of 1933, as amended, or any similar federal statute, and the rules and regulations of the Commission issued under such Act, as they each may, from time to time, be in effect.

        " SG Cowen Warrants " means one or more warrants granted to SG Cowen pursuant to the letter agreement between the Company and SG Cowen dated April 6, 2000, as amended by the letter agreement dated February 2, 2001.

        " Shares " means the Company's outstanding Series A Convertible Preferred Stock, $.001 par value per share, the Series B Convertible Preferred Stock, $.001 par value per share, and the Series C Preferred Stock.

        " Stockholders " means the Investors and any persons or entities to whom the rights granted to the Investors under this Agreement are transferred by the Investors, their successors or permitted assigns pursuant to Section 5.2 below.

ARTICLE II. REGISTRATION RIGHTS

        2.1.     Required Registrations.     

        (a)   At any time after the earlier of (i) six (6) months after the closing of the Company's first underwritten public offering of shares of Common Stock pursuant to a Registration Statement or (ii) the second anniversary of the date hereof, a Stockholder or Stockholders or SG Cowen (each a " Holder " and, collectively, the " Holders ") may request, in writing, that the Company effect the registration on Form S-1 or Form S-2 (or any successor form) of Registrable Shares owned by such Holders having an aggregate offering price of at least $7,500,000 (based on the market price or fair value at the time of such request). Upon receipt of any such request, the Company shall promptly give written notice of such proposed registration to all Holders. Such Holders shall have the right, by giving written notice to the Company within ten (10) business days after the Company provides its notice, to elect to have included in such registration such of their Registrable Shares as such Holders may request in such notice of election. If the Holders initiating the registration intend to distribute the Registrable Shares by means of an underwriting, they shall so advise the Company in their request. Thereupon, the Company shall, as expeditiously as possible, use its reasonable best efforts to effect the registration on Form S-1 or Form S-2 (or any successor form) of all Registrable Shares which the Company has been requested to so register.

        (b)   At any time after the Company becomes eligible to file a Registration Statement on Form S-3 (or any successor form relating to secondary offerings), a Holder or Holders may request the Company, in writing, to effect the registration on Form S-3 (or such successor form), of Registrable Shares having

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an aggregate offering price of at least $1,000,000 (based on the public market price at the time of such request). Upon receipt of any such request, the Company shall promptly give written notice of such proposed registration to all Holders. Such Holders shall have the right, by giving written notice to the Company within ten (10) business days after the Company provides its notice, to elect to have included in such registration such of their Registrable Shares as such Holders may request in such notice of election; provided, however, that if the underwriter (if any) managing the offering determines that, because of marketing factors, not all of the Registrable Shares requested to be registered by all of the Holders may be included in the offering, then, all securities held by other parties shall first be excluded, and thereafter all Holders who have requested registration shall participate in the registration pro rata based upon the number of Registrable Shares which they have requested to be so registered (the " Requested Investor Shares "). Thereupon, subject to this Section 2.1(b), the Company shall, as expeditiously as possible, use its best efforts to effect the registration on Form S-3 (or such successor form) of all Registrable Shares which the Company has been requested to so register. The Company shall have the right to approve (such approval to not be unreasonably withheld) the managing underwriter of any underwritten offering effected pursuant to Section 2.1(a) or this Section 2.1(b).

        (c)   The Company shall not be required to effect more than two registrations pursuant to paragraph (a) above; provided, however, that such obligations shall be deemed satisfied only when a registration statement covering the applicable Registrable Shares shall have (i) become effective or (ii) been withdrawn at the request of the Holders requesting such registration (other than as a result of information concerning the business or financial condition of the Company which is made known to the Holders after the date on which such registration was requested).

        (d)   If at the time of any request to register Registrable Shares pursuant to this Section 2.1, the Company is engaged or has plans to engage within 60 days of the time of the request in a registered public offering of securities for its own account or is engaged in any other activity which, in the good faith determination of the Company's Board of Directors, would be adversely affected by the requested registration to the material detriment of the Company, then the Company may at its option direct that such request be delayed for a period not in excess of three months from the effective date of such offering or the date of commencement of such other material activity, as the case may be, such right to delay a request to be exercised by the Company not more than once in any 12-month period.

        2.2.     Incidental Registration.     

        Except for the Company's first underwritten public offering of shares of Common Stock pursuant to a Registration Statement, whenever the Company proposes to file a Registration Statement at any time and from time to time, it will, prior to such filing, give written notice to all Holders of its intention to do so and, upon the written request of a Holder or Holders, given within ten (10) business days after the Company provides such notice (which request shall state the intended method of disposition of such Registrable Shares), the Company shall use its best efforts to cause all Registrable Shares which the Company has been requested by such Holder or Holders to register, to be registered under the Securities Act to the extent necessary to permit their sale or other disposition in accordance with the intended methods of distribution specified in the request of such Holder or Holders; provided, however, that the Company shall have the right to postpone or withdraw any registration effected pursuant to this Section 2.2 without obligation to any Holder.

        (b)   In connection with any registration under this Section 2.2 involving an underwriting, the Company shall not be required to include any Registrable Shares in such registration unless the holders thereof accept the terms of the underwriting as agreed upon between the Company and the underwriters selected by it. If in the opinion of the managing underwriter it is desirable because of marketing factors to limit the number of Registrable Shares to be included in the offering, then the Company shall be required to include in the registration only that number of Registrable Shares, if any, which the managing underwriter believes should be included therein; provided, however, that no

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persons or entities other than the Company, the Holders and other persons or entities holding registration rights shall be permitted to include securities in the offering. If the number of Registrable Shares to be included in the offering in accordance with the foregoing is less than the total number of shares which the holders of Registrable Shares have requested to be included, then, all securities held by other parties shall first be excluded, and thereafter the holders of Registrable Shares who have requested registration shall participate in the registration pro rata based upon their total ownership of shares of Common Stock (giving effect to the conversion into Common Stock of all convertible securities). If any holder would thus be entitled to include more securities than such holder requested to be registered, the excess shall be allocated among other requesting holders pro rata in the manner described in the preceding sentence.

        2.3.     Registration Procedures.     If and whenever the Company is required by the provisions of this Agreement to use its best efforts to effect the registration of any of the Registrable Shares under the Securities Act, the Company shall:

        (a)   file with the Commission a Registration Statement with respect to such Registrable Shares and use its best efforts to cause that Registration Statement to become effective;

        (b)   as expeditiously as possible prepare and file with the Commission any amendments and supplements to the Registration Statement and the prospectus included in the Registration Statement as may be necessary to keep the Registration Statement effective, in the case of a firm commitment underwritten public offering, until each underwriter has completed the distribution of all securities purchased by it and, in the case of any other offering, until the earlier of the sale of all Registrable Shares covered thereby or 120 days after the effective date thereof;

        (c)   as expeditiously as possible furnish to each selling Holder such reasonable number of copies of the prospectus, including any preliminary prospectus, in conformity with the requirements of the Securities Act, and such other documents as the selling Holder may reasonably request in order to facilitate the public sale or other disposition of the Registrable Shares owned by the selling Holder; and

        (d)   as expeditiously as possible use its best efforts to register or qualify the Registrable Shares covered by the Registration Statement under the securities or Blue Sky laws of such states as the selling Holders shall reasonably request, and do any and all other acts and things that may be necessary or desirable to enable the selling Holders to consummate the public sale or other disposition in such states of the Registrable Shares owned by the selling Holders; provided, however, that the Company shall not be required in connection with this paragraph (d) to qualify as a foreign corporation or execute a general consent to service of process in any jurisdiction; and

        If the Company has delivered preliminary or final prospectuses to the selling Holders and after having done so the prospectus is amended to comply with the requirements of the Securities Act, the Company shall promptly notify the selling Holders and, if requested, the selling Holders shall immediately cease making offers of Registrable Shares and return all prospectuses to the Company. The Company shall promptly provide each selling Holder with revised prospectuses and, following receipt of the revised prospectuses, the selling Holder shall be free to resume making offers of the Registrable Shares.

        Notwithstanding the foregoing, each selling Holder shall cease making offers or sales pursuant to a "shelf" Registration Statement during any Postponement Period (not to exceed 90 days in the aggregate in any 12-month period). A " Postponement Period " shall be any period in which there exists at the time material non-public information relating to the Company disclosure of which the Company, in its good faith judgment by the Board of Directors, reasonably believes:

          (i)  that the filing thereof at the time requested, or the offering of Registrable Shares pursuant thereto, would materially and adversely affect (A) a pending or scheduled public offering or private placement of the Company's securities, (B) an acquisition, merger, consolidation or any

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other similar transaction by or of the Company, or (C) pre-existing and continuing negotiations, discussions or pending proposals with respect to any of the foregoing transactions; and

         (ii)  that the failure to disclose any material information with respect to the foregoing would cause a violation of the Securities Act or the Exchange Act.

        If, after a registration statement becomes effective, the Company becomes engaged in any activity which, in the good faith determination of the Company's Board of Directors, involves information that would have to be disclosed in the Registration Statement but which the Company desires to keep confidential for valid business reasons, including any event giving rise to a Postponement Period, then the Company may at its option, by notice to such Holders, require that the Holders who have included Shares in such Registration Statement cease sales of such Shares under such Registration Statement for a period not in excess of 90 days in the aggregate in any 12-month period. If, in connection therewith, the Company considers it appropriate for such Registration Statement to be amended, the Company shall so amend such Registration Statement as promptly as practicable and such Holders shall suspend any further sales of their Shares until the Company advises them that such Registration Statement has been amended. The time periods referred to in this Section 2.3 during which such Registration Statement must be kept effective shall be extended for an additional number of days equal to the number of days during which the right to sell shares was suspended pursuant to this paragraph.

        2.4.     Allocation of Expenses.     The Company will pay all Registration Expenses of all registrations under this Agreement; provided, however, that if a registration under Section 2.1 is withdrawn at the request of the initiating Holders (other than as a result of information concerning the business or financial condition of the Company which is made known to the Holders after the date on which such registration was requested) and if the initiating Holders elect not to have such registration counted as a registration requested under Section 2.1, the requesting Holders shall pay the Registration Expenses of such registration pro rata in accordance with the number of their Registrable Shares included in such registration or in such other manner as they may among themselves agree. For purposes of this Section 2.4, the term " Registration Expenses " shall mean all expenses incurred by the Company in complying with Article II, including, without limitation, all registration and filing fees, exchange listing fees, printing expenses, fees and expenses of counsel for the Company and the reasonable fees and expenses of one counsel selected by the selling Holder(s) to represent the selling Holder(s), state Blue Sky fees and expenses, the expense of any special audits incident to or required by any such registration, but excluding underwriting discounts, selling commissions and the fees and expenses of any Selling Holders' counsel other than one counsel referred to above.

        2.5.     Indemnification and Contribution.     

        (a)   In the event of any registration of any of the Registrable Shares under the Securities Act pursuant to this Agreement, the Company will indemnify and hold harmless the seller of such Registrable Shares, the partners, members, officers, directors and stockholders of such seller of Registrable Shares, each underwriter of such Registrable Shares, and each other person, if any, who controls such seller or underwriter within the meaning of the Securities Act or the Exchange Act against any losses, claims, damages or liabilities, joint or several, to which such seller, underwriter or controlling or aforementioned person may become subject under the Securities Act, the Exchange Act, state securities or Blue Sky laws or otherwise, insofar as such losses, claims, damages or liabilities (or actions in respect thereof) arise out of or are based upon any untrue statement or alleged untrue statement of any material fact contained in any Registration Statement under which such Registrable Shares were registered under the Securities Act, any preliminary prospectus or final prospectus contained in the Registration Statement, or any amendment or supplement to such Registration Statement, or arise out of or are based upon the omission or alleged omission to state a material fact required to be stated therein or necessary to make the statements therein not misleading or arise out of or are based upon any violation or alleged violation by the Company of the Securities Act, the

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Exchange Act, state securities or Blue Sky laws; and the Company will reimburse such seller, underwriter and each such controlling or aforementioned person for any legal or any other expenses reasonably incurred by such seller, underwriter or controlling person in connection with investigating or defending any such loss, claim, damage, liability or action as such expenses are incurred; provided, however, that the Company will not be liable in any such case to the extent that any such loss, claim, damage or liability arises out of or is based upon any untrue statement or omission made in such Registration Statement, preliminary prospectus or final prospectus, or any such amendment or supplement, in reliance upon and in conformity with information furnished to the Company, in writing, by or on behalf of such seller, underwriter or controlling person specifically for use in the preparation thereof.

        (b)   In the event of any registration of any of the Registrable Shares under the Securities Act pursuant to this Agreement, each seller of Registrable Shares, severally and not jointly, will indemnify and hold harmless the Company, each of its directors and officers, each other seller of Registrable Shares and each underwriter (if any) and each person, if any, who controls the Company or any such other seller or underwriter within the meaning of the Securities Act or the Exchange Act, against any losses, claims, damages or liabilities, joint or several, to which the Company, such directors and officers, other seller, underwriter or controlling person may become subject under the Securities Act, Exchange Act, state securities or Blue Sky laws or otherwise, insofar as such losses, claims, damages or liabilities (or actions in respect thereof) arise out of or are based upon any untrue statement or alleged untrue statement of a material fact contained in any Registration Statement under which such Registrable Shares were registered under the Securities Act, any preliminary prospectus or final prospectus contained in the Registration Statement, or any amendment or supplement to the Registration Statement, or arise out of or are based upon any omission or alleged omission to state a material fact required to be stated therein or necessary to make the statements therein not misleading, if the statement or omission was made in reliance upon and in conformity with information relating to such seller furnished in writing to the Company by or on behalf of such seller specifically for use in connection with the preparation of such Registration Statement, prospectus, amendment or supplement; provided, however, that the obligations of such Holders hereunder shall be limited to an amount equal to the net proceeds to each Holder of Registrable Shares sold in connection with such registration.

        (c)   Each party entitled to indemnification under this Section 2.5 (the " Indemnified Party ") shall give notice to the party required to provide indemnification (the " Indemnifying Party ") promptly after such Indemnified Party has actual knowledge of any claim as to which indemnity may be sought, and shall permit the Indemnifying Party to assume the defense of any such claim or any litigation resulting therefrom; provided, however, that counsel for the Indemnifying Party, who shall conduct the defense of such claim or litigation, shall be approved by the Indemnified Party (whose approval shall not be unreasonably withheld); and, provided that the failure of any Indemnified Party to give notice as provided herein shall not relieve the Indemnifying Party of its obligations under this Section 2.5, unless and except to the extent that the Indemnifying Party is prejudiced by the failure of the Indemnified Party to provide timely notice. The Indemnified Party may participate in such defense at such party's expense; provided, however, t