Warrant to Purchase Stock



 Exhibit 4.1 
 THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AND PURSUANT TO THE PROVISIONS OF ARTICLE 5 BELOW,
MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAW OR, IN THE OPINION OF LEGAL COUNSEL IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER OF THESE
SECURITIES, SUCH OFFER, SALE OR TRANSFER, PLEDGE OR HYPOTHECATION IS EXEMPT FROM REGISTRATION. 
 WARRANT TO PURCHASE STOCK 

 

			
	Corporation:	  	EGAIN COMMUNICATIONS CORPORATION
	Number of Shares:	  	73,889 ($66,500/ Initial Exercise Price)
	Class of Stock:	  	Common
	Initial Exercise Price:	  	$0.90 (average trading price in the preceding 5 days prior to execution of warrant)
	Issue Date:	  	June 24, 2008
	Expiration Date:	  	June 24, 2011

 THIS WARRANT CERTIFIES THAT,
for good and valuable consideration, the receipt of which is hereby acknowledged, BRIDGE BANK N.A. or its assignee (“Holder”) is entitled to purchase the number of fully paid and
nonassessable shares of the class of securities (the “Shares”) of the corporation (the “Company”) at the initial exercise price per Share (the “Warrant Price”) all as set forth
above and as adjusted pursuant to Article 2 of this warrant, subject to the provisions and upon the terms and conditions set forth in this warrant. 
 ARTICLE 1 
 EXERCISE 
 1.1 Method of Exercise. Holder may exercise this warrant by delivering this warrant and a duly executed Notice of Exercise in substantially the form attached as Appendix 1 to the principal office of the
Company. Unless Holder is exercising the conversion right set forth in Section 1.2, Holder shall also deliver to the Company a check for the aggregate Warrant Price for the Shares being purchased. 
 1.2 Conversion Right. In lieu of exercising this warrant as specified in Section 1.1, Holder may from time to time convert this warrant, in
whole or in part, into a number of Shares determined by dividing (a) the aggregate fair market value of the Shares or other securities otherwise issuable upon exercise of this warrant minus the aggregate Warrant Price of such Shares by
(b) the fair market value of one Share. The fair market value of the Shares shall be determined pursuant to Section 1.3. 
 1.3
Fair Market Value. If the Shares are traded regularly in a public market, the fair market value of the Shares shall be the closing price of the Shares (or the closing price of the Company’s stock into which the Shares are convertible)
reported for the business day immediately before Holder delivers its Notice of Exercise to the Company. If the Shares are not regularly traded in a public market, the Board of Directors of the Company shall determine fair market value in its
reasonable good faith judgment. 
 1.4 Put Option. Upon the Expiration Date or an Exit Event, Holder shall have the right to require
the Company to purchase the Warrant in consideration of the Company’s payment to Holder (due twenty (20) business days after receipt of Holder’s written notice) of $133,000. An “Exit Event” is defined herein as one of the
following: (i) the early termination of the loan from Holder to Company pursuant to that certain Loan and Security Agreement dated June 24, 2008 (the “Loan Agreement”); (ii) a Change in Control (as defined under the Loan
Agreement); (iii) a sale of substantially all of the equity ownership of Company; (iv) an uncured Event of Default under the Loan Agreement (as defined under the Loan Agreement); and (v) June 24, 2011. 
  

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 1.5 Delivery of Certificate and New Warrant. Promptly after Holder exercises or converts this
warrant, the Company shall deliver to Holder certificates for the Shares acquired and, if this warrant has not been fully exercised or converted and has not expired, a new warrant representing the Shares not so acquired. 
 1.6 Replacement of Warrants. On receipt of evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation of this
warrant and, in the case of loss, theft or destruction, on delivery of an indemnity agreement reasonably satisfactory in form and amount to the Company or, in the case of mutilation, on surrender and cancellation of this warrant, the Company at its
expense shall execute and deliver, in lieu of this warrant, a new warrant of like tenor. 
 ARTICLE 2 
 ADJUSTMENTS TO THE SHARES 
 2.1
Stock Dividends, Splits, Etc. If the Company declares or pays a dividend on its common stock payable in common stock, or other securities, or subdivides the outstanding common stock into a greater amount of common stock, then upon exercise of
this warrant, for each Share acquired, Holder shall receive, without cost to Holder, the total number and kind of securities to which Holder would have been entitled had Holder owned the Shares of record as of the date the dividend or subdivision
occurred. 
 2.2 Reclassification, Exchange or Substitution. Upon any reclassification, exchange, substitution, or other event that
results in a change of the number and/or class of the securities issuable upon exercise or conversion of this warrant, Holder shall be entitled to receive, upon exercise or conversion of this warrant, the number and kind of securities and property
that Holder would have received for the Shares if this warrant had been exercised immediately before such reclassification, exchange, substitution, or other event. The Company or its successor shall promptly issue to Holder a new warrant for such
new securities or other property. The new warrant shall provide for adjustments which shall be as nearly equivalent as may be practicable to the adjustments provided for in this Article 2 including, without limitation, adjustments to the Warrant
Price and to the number of securities or property issuable upon exercise of the new warrant. The provisions of this Section 2.2 shall similarly apply to successive reclassifications, exchanges, substitutions, or other events. 
 2.3 Adjustments for Mergers, Combinations, Etc. If the outstanding Shares are combined or consolidated, by reclassification or otherwise, into a
lesser number of shares, the Warrant Price shall be proportionately increased. If the outstanding Shares are combined or consolidated, by reclassification or otherwise, into a greater number of shares, the Warrant Price shall be proportionately
decreased. Upon the closing of any acquisition of all or substantially all of Holder’s assets or capital stock, the successor entity shall assume the obligations of this warrant, then this warrant shall be exercisable for the same securities,
cash, and property as would be payable for the Shares issuable upon exercise of the unexercised portion of this warrant as if such Shares were outstanding on the record date for the acquisition and subsequent closing. The Warrant Price shall be
adjusted accordingly. 
 2.4 No Impairment. The Company shall not, by amendment of its Certificate of Incorporation or through a
reorganization, transfer of assets, consolidation, merger, dissolution, issue, or sale of securities or any other voluntary action, avoid or seek to avoid the observance or performance of any of the terms to be observed or performed under this
warrant by the Company, but shall at all times in good faith assist in carrying out all the provisions of this Article 2 and in taking all such action as may be necessary or appropriate to protect Holder’s rights under this Article against
impairment, provided, however, this Section 2.4 shall not restrict or impair the Company’s right to effect any amendment of its Certificate of Incorporation, reorganization, transfer of assets, consolidation, merger, dissolution, issue or
sale of securities or any other voluntary action so long as such amendment, transaction or action affects the rights associated with the Shares in the same manner as such amendment, transaction or action affects the rights associated with all other
shares of the class of securities comprising the Shares. 
 2.5 Certificate as to Adjustments. Upon each adjustment of the Warrant
Price, the Company at its expense shall promptly compute such adjustment, and furnish Holder with a certificate of its Chief Financial Officer setting forth such adjustment and the facts upon which such adjustment is based. The Company shall, upon
written request, furnish Holder a certificate setting forth the Warrant Price in effect upon the date thereof and the series of adjustments leading to such Warrant Price. 
  


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 2.6 Fractional Shares. No fractional Shares shall be issuable upon exercise or conversion of the
Warrant and the Number of Shares to be issued shall be rounded down to the nearest whole Share. If a fractional share interest arises upon any exercise or conversion of the Warrant, the Company shall eliminate such fractional share interest by
paying Holder amount computed by multiplying the fractional interest by the fair market value of a full Share. 
 ARTICLE 3 

REPRESENTATIONS AND COVENANTS OF THE COMPANY 
 3.1 Representations and Warranties. The Company hereby represents and warrants to the Holder as follows: 
 (a) The initial Warrant Price referenced on the first page of this warrant is not greater than the fair market value of the Shares as of the date of this warrant. 
 (b) All Shares which may be issued upon the exercise of the purchase right represented by this warrant, and all securities, if any, issuable upon
conversion of the Shares, shall, upon issuance, be duly authorized, validly issued, fully paid and nonassessable, and free of any liens and encumbrances except for restrictions on transfer provided for herein or under applicable federal and state
securities laws. 
 (c) The Company’s capitalization table attached to this warrant is true and complete as of the Issue Date.

 3.2 Notice of Certain Events. If the Company proposes at any time (a) to declare any dividend or distribution upon its common
stock, whether in cash, property, stock, or other securities and whether or not a regular cash dividend; (b) to offer for subscription pro rata generally to the holders of its common stock any additional shares of stock of any class or series
or other rights; (c) to effect any reclassification or recapitalization of common stock; or (d) to merge or consolidate with or into any other corporation, or sell, lease, license, or convey all or substantially all of its assets, or to
liquidate, dissolve or wind up, then, in connection with each such event, the Company shall give Holder (1) at least 20 days prior written notice (or such shorter period of notice as the Company provides to its stockholders consistent with its
Certificate of Incorporation) of the date on which a record will be taken for such dividend, distribution, or subscription rights (and specifying the date on which the holders of common stock will be entitled thereto) or for determining rights to
vote, if any, in respect of the matters referred to in (a) and (b) above; and (2) in the case of the matters referred to in (c) and (d) above at least 20 days prior written notice (or such shorter period of notice as the
Company provides to its stockholders consistent with its Certificate of Incorporation) of the date when the same will take place (and specifying the date on which the holders of common stock will be entitled to exchange their common stock for
securities or other property deliverable upon the occurrence of such event). 
 3.3 Information Rights. So long as the Holder holds
this warrant and/or any of the Shares, at such time as Company is not subject to the reporting requirements of the Securities Act of 1933, as amended, the Company shall deliver to the Holder (a) promptly after mailing, copies of all communiques
to the shareholders of the Company, (b) within ninety (90) days after the end of each fiscal year of the Company, the annual audited financial statements of the Company certified by independent public accountants of recognized standing and
(c) within forty-five (45) days after the end of each of the first three quarters of each fiscal year, the Company’s quarterly, unaudited financial statements. 
  

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 ARTICLE 4 
 MISCELLANEOUS 
 4.1 Term: Exercise Upon Expiration. This warrant is exercisable in whole or in
part, at any time and from time to time on or before the Expiration Date set forth above; provided, however, that if the Company completes its initial public offering within the three-year period immediately prior to the Expiration Date, the
Expiration Date shall automatically be extended until the third anniversary of the effective date of the Company’s initial public offering. If this warrant has not been exercised prior to the Expiration Date, this warrant shall be deemed to
have been automatically exercised on the Expiration Date by “cashless” conversion pursuant to Section 1.2. 
 4.2 Legends.
This warrant and the Shares (and the securities issuable, directly or indirectly, upon conversion of the Shares, if any) shall be imprinted with a legend in substantially the following form: 
 THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED UNLESS
AND UNTIL REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAW OR, IN THE OPINION OF LEGAL COUNSEL IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER OF THESE SECURITIES, SUCH OFFER, SALE OR TRANSFER, PLEDGE OR HYPOTHECATION IS EXEMPT FROM
REGISTRATION. 
 4.3 Compliance with Securities Laws on Transfer. This warrant and the Shares issuable upon exercise of this warrant
(and the securities issuable, directly or indirectly, upon conversion of the Shares, if any) may not be transferred or assigned in whole or in part without compliance with applicable federal and state securities laws by the transferor and the
transferee. 
 4.4 Transfer Procedure. Subject to the provisions of Section 4.3, Holder may transfer all or part of this warrant
or the Shares issuable upon exercise of this warrant (or the securities issuable, directly or indirectly, upon conversion of the Shares, if any) by giving the Company notice of the portion of the warrant being transferred setting forth the name,
address and taxpayer identification number of the transferee and surrendering this warrant to the Company for reissuance to the transferee(s) (and Holder, if applicable). 
 4.5 Notices. All notices and other communications from the Company to the Holder, or vice versa, shall be deemed delivered and effective when given personally or mailed by first-class registered or certified
mail, postage prepaid, at such address as may have been furnished to the Company or the Holder, as the case may be, in writing by the Company or such Holder from time to time. All notices to the Holder shall be addressed as follows: 
 Bridge Bank N.A. 
 55 Almaden Blvd.

 San Jose, CA 95113 
 Attn:
Technology Division 
 4.6 Amendments. This warrant and any term hereof may be changed, waived, discharged or terminated only by an
instrument in writing signed by the party against which enforcement of such change, waiver, discharge or termination is sought. 
 4.7
Attorneys’ Fees. In the event of any dispute between the parties concerning the terms and provisions of this warrant, the party prevailing in such dispute shall be entitled to collect from the other party all costs incurred in such dispute,
including reasonable attorneys’ fees. 
 4.8 Governing Law. This warrant shall be governed by and construed in accordance with
the laws of the State of California, without giving effect to its principles regarding conflicts of law. 
  

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	EGAIN COMMUNICATIONS CORPORATION
		
	By:	 	 /s/ Eric Smit

	Name:	 	Eric Smit
	Title:	 	Chief Financial Officer


  

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