Warrant to Purchase Common Stock



 Exhibit 4.1 
 THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933. SUCH SECURITIES AND ANY SECURITIES OR SHARES ISSUED HEREUNDER MAY NOT BE SOLD OR TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR AN EXEMPTION
THEREFROM UNDER SAID ACT. COPIES OF THE AGREEMENT COVERING THE PURCHASE OF THESE SECURITIES AND RESTRICTING THEIR TRANSFER OR SALE MAY BE OBTAINED AT NO COST BY WRITTEN REQUEST MADE BY THE HOLDER OF RECORD HEREOF TO THE SECRETARY OF THE COMPANY AT
ITS PRINCIPAL EXECUTIVE OFFICES. 
 No. WC-2007-A 
 WARRANT TO PURCHASE COMMON STOCK 
 OF 
 eGAIN COMMUNICATIONS CORPORATION 
 This certifies that, for value received, Ashutosh Roy or his
registered assigns (“Holder”) is entitled, subject to the terms and conditions set forth below, to purchase from eGAIN COMMUNICATIONS CORPORATION (the “Company”), in whole or in part that number of
fully paid and nonassessable shares (the “Warrant Shares”) of Common Stock (as defined below) determined in accordance with Section 2 below and at a purchase price per share (the “Exercise Price”)
determined in accordance with Section 2 below. The number, character and Exercise Price of such shares of Common Stock are subject to adjustment as provided below and all references to “Warrant Shares” and “Exercise Price”
herein shall be deemed to include any such adjustment or series of adjustments. The term “Warrant” as used herein shall mean this Warrant, and any warrants delivered in substitution or exchange therefor as provided herein. This Warrant is
issued in connection with the issuance by the Company of a certain Subordinated Secured Promissory Note of even date herewith (the “Note”) issued pursuant to that certain Note and Warrant Purchase Agreement and Amendment to
Subordinated Secured Promissory Notes (the “Purchase Agreement”) by and between the Company and Holder dated as of June 29, 2007. 
 1. Term of Warrant. Subject to the terms and conditions set forth herein, this Warrant shall be exercisable, in whole or in part, during the term commencing on the date hereof and ending at 5:00 p.m.,
Pacific time, three (3) years from the date hereof, and shall be void thereafter (the “Exercise Period”). 
 2.
Exercise Price; Common Stock; Number of Shares. 
 (a) Exercise Price. The term “Exercise Price” shall mean the
greater of (i) $1.20 (as adjusted for stock splits, dividends and combinations occurring after the date hereof) or (ii) one hundred ten percent (110%) of the fair market value of one (1) share of Common Stock, such fair market
value to be determined based on the average closing price of the Common Stock for the fifteen (15) consecutive trading days immediately prior to but not including the date of the Note, on the OTC Bulletin Board. 







 (b) Common Stock. The term “Common Stock” shall mean the Company’s
common stock, par value $0.001 per share. 
 (c) Number of Shares. Subject to the provisions of Section 1, this Warrant shall be
exercisable for up to that number of shares of Common Stock determined according to the following formula: 
  

			
	x =	  	    $400,000    
		  	Exercise Price
		
	x =	  	the maximum number of shares of Common Stock which may be purchased.

 The number of shares subject to the Warrant shall be subject to adjustment as set forth in Section 11.

 3. Exercise of Warrant. 
 (a) Cash Exercise. This Warrant may be exercised by the Holder during the Exercise Period by (i) the surrender of this Warrant to the Company, with the Notice of Exercise annexed hereto duly completed and executed on behalf of
the Holder, at the office of the Company (or such other office or agency of the Company as it may designate by notice in writing to the Holder at the address of the Holder appearing on the books of the Company) during the Exercise Period and
(ii) the delivery of payment to the Company, for the account of the Company, by cash, wire transfer of immediately available funds to a bank account specified by the Company, or by certified or bank cashier’s check, of the Exercise Price
for the number of Warrant Shares specified in the Exercise Form in lawful money of the United States of America. The Company agrees that such Warrant Shares shall be deemed to be issued to the Holder as the record holder of such Warrant Shares as of
the close of business on the date on which this Warrant shall have been surrendered and payment made for the Warrant Shares as aforesaid. A stock certificate or certificates for the Warrant Shares specified in the Exercise Form shall be delivered to
the Holder as promptly as practicable, and in any event within 10 days, thereafter. If this Warrant shall have been exercised only in part, the Company shall, at the time of delivery of the stock certificate or certificates, deliver to the Holder a
new Warrant evidencing the rights to purchase the remaining Warrant Shares, which new Warrant shall in all other respects be identical with this Warrant. 
 (b) Net Issue Exercise. In lieu of exercising this Warrant pursuant to Section 3(a), this Warrant may be exercised by the Holder by the surrender of this Warrant to the Company, with a duly executed
Exercise Form marked to reflect Net Issue Exercise and specifying the number of shares of Common Stock to be purchased, during normal business hours on any Business Day during the Exercise Period. The Company agrees that such shares of Common Stock
shall be deemed to be issued to the Holder as the record holder of such shares of Common Stock as of the close of business on the date on which this Warrant shall have been surrendered as aforesaid. Upon such exercise, the Holder shall be entitled
to receive shares equal to the value of this Warrant (or the portion thereof being canceled) by surrender of this Warrant to the 

  

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Company together with notice of such election in which event the Company shall issue to Holder a number of shares of Common Stock computed as of the date of
surrender of this Warrant to the Company using the following formula: 
  

			
	X =	  	Y(A-B)
		  	     A

  

					
	Where	 	X =	  	the number of shares of Common Stock to be issued to Holder under this Section 3(b);
			
		 	Y =	  	the number of shares of Common Stock otherwise purchasable under this Warrant (as adjusted to the date of such calculation);
			
		 	A =	  	the fair market value of one share of the Common Stock at the date of such calculation; and
			
		 	B =	  	the Exercise Price (as adjusted to the date of such calculation).

 (c) Fair Market Value. For purposes of Section 3(b) only, fair market value of one
share of the Company’s Common Stock shall mean, as of any date: 
 (i) the last closing price per share of the
Company’s Common Stock on the principal national securities exchange on which the Common Stock is listed or admitted to trading, or 
 (ii) the last reported sales price per share of the Company’s Common Stock on the Nasdaq Stock Market (“Nasdaq”) or the OTC Bulletin Board (the “OTCBB”) if the
Company’s Common Stock is not listed or traded on any such exchange, or 
 (iii) the average of the bid and asked price
per share as reported in the “pink sheets” published by the National Quotation Bureau, Inc. (the “pink sheets”) if the Company’s Common Stock is not listed or traded on any exchange, Nasdaq or the OTCBB, or

 (iv) if such quotations are not available, the fair market value per share of the Company’s Common Stock on the date
such notice was received by the Company as reasonably determined in good faith by the Board of Directors of the Company. 
 (d) This Warrant
shall be deemed to have been exercised immediately prior to the close of business on the date of its surrender for exercise as provided above, and the person entitled to receive the shares of Common Stock issuable upon such exercise shall be treated
for all purposes as the holder of record of such shares as of the close of business on such date. As promptly as practicable on or after such date and in any event within ten (10) days thereafter, the Company at its expense shall issue and
deliver to the person or persons entitled to receive the same a certificate or certificates for the number of shares issuable upon such exercise. In the event that this Warrant is exercised in part, the Company at its expense will execute and
deliver a new Warrant of like tenor exercisable for the number of shares for which this Warrant may then be exercised. 
  

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 4. No Fractional Shares or Scrip. No fractional shares or scrip representing fractional shares
shall be issued upon the exercise of this Warrant. In lieu of any fractional share to which the Holder would otherwise be entitled, the Company shall make a cash payment equal to the Exercise Price multiplied by such fraction. 
 5. Replacement of Warrant. 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 substance 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 and amount. 
 6. Rights of Stockholders.
Subject to Sections 9 and 11 of this Warrant, the Holder shall not be entitled to vote or receive dividends or be deemed the holder of Common Stock or any other securities of the Company that may at any time be issuable on the exercise hereof
for any purpose, nor shall anything contained herein be construed to confer upon the Holder, as such, any of the rights of a stockholder of the Company or any right to vote for the election of directors or upon any matter submitted to stockholders
at any meeting thereof, or to give or withhold consent to any corporate action (whether upon any recapitalization, issuance of stock, reclassification of stock, change of par value, or change of stock to no par value, consolidation, merger,
conveyance, or otherwise) or to receive notice of meetings, or to receive dividends or subscription rights or otherwise until the Warrant shall have been exercised as provided herein. 
 7. Transfer of Warrant. 
 (a)
Warrant Register. The Company will maintain a register (the “Warrant Register”) containing the names and addresses of the Holder or Holders. Any Holder of this Warrant or any portion thereof may change his address as
shown on the Warrant Register by written notice to the Company requesting such change. Any notice or written communication required or permitted to be given to the Holder may be delivered or given by mail to such Holder as shown on the Warrant
Register and at the address shown on the Warrant Register. Until this Warrant is transferred on the Warrant Register of the Company, the Company may treat the Holder as shown on the Warrant Register as the absolute owner of this Warrant for all
purposes, notwithstanding any notice to the contrary. 
 (b) Warrant Agent. The Company may, by written notice to the Holder, appoint
an agent for the purpose of maintaining the Warrant Register referred to in Section 7(a) above, issuing the Warrant Shares or other securities then issuable upon the exercise of this Warrant, exchanging this Warrant, replacing this Warrant, or
any or all of the foregoing. Thereafter, any such registration, issuance, exchange, or replacement, as the case may be, shall be made at the office of such agent. 
 (c) Transferability and Nonnegotiability of Warrant. This Warrant may only be transferred or assigned in whole or in part in accordance with the transfer and assignment provisions set forth in Section 9.13
of the Purchase Agreement and compliance with all applicable federal and state securities laws by the transferor and the transferee (including the delivery of investment representation letters and legal opinions reasonably satisfactory to the


  

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Company, if such are requested by the Company). Notwithstanding the foregoing, no investment representation letter or opinion of counsel shall be required
for any transfer of this Warrant (or any portion thereof) or any shares of Common Stock issued upon exercise hereof (i) in compliance with Rule 144 or Rule 144A of the Act, or (ii) by gift, will or intestate succession by the
Holder to his or her spouse or lineal descendants or ancestors or any trust for any of the foregoing; provided that in each of the foregoing cases the transferee agrees in writing to be subject to the terms of this Section 7(c). Subject to the
provisions of this Warrant with respect to compliance with the Securities Act of 1933, as amended (the “Act”), title to this Warrant may be transferred by endorsement (by the Holder executing the Assignment Form annexed
hereto) and delivery in the same manner as a negotiable instrument transferable by endorsement and delivery. 
 (d) Exchange of Warrant
Upon a Transfer. On surrender of this Warrant for exchange, properly endorsed on the Assignment Form and subject to the provisions of this Warrant with respect to compliance with the Act and with the limitations on assignments and transfers and
contained in this Section 7, the Company at its expense shall issue to or on the order of the Holder a new warrant or warrants of like tenor, in the name of the Holder or as the Holder (on payment by the Holder of any applicable transfer taxes)
may direct, for the number of shares issuable upon exercise hereof. 
 (e) Compliance with Securities Laws. 
 (i) The Holder of this Warrant, by acceptance hereof, acknowledges that this Warrant and the shares of Common Stock to be issued upon
exercise hereof are being acquired solely for the Holder’s own account and not as a nominee for any other party, and for investment, and that the Holder will not offer, sell or otherwise dispose of this Warrant or any shares of Common Stock to
be issued upon exercise hereof except under circumstances that will not result in a violation of the Act or any applicable state securities laws. Upon exercise of this Warrant, the Holder shall, if requested by the Company, confirm in writing, in a
form satisfactory to the Company, that the shares of Common Stock so purchased are being acquired solely for the Holder’s own account and not as a nominee for any other party, for investment, and not with a view toward distribution or resale.

 (ii) This Warrant and all shares of Common Stock issued upon exercise hereof shall be stamped or imprinted with a legend in
substantially the following form (in addition to any legend required by state securities laws): 
 THE SECURITIES REPRESENTED HEREBY HAVE NOT
BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933. SUCH SECURITIES AND ANY SECURITIES OR SHARES ISSUED HEREUNDER MAY NOT BE SOLD OR TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR AN EXEMPTION THEREFROM UNDER SAID ACT. COPIES OF THE AGREEMENT
COVERING THE PURCHASE OF THESE SECURITIES AND RESTRICTING THEIR TRANSFER OR SALE MAY BE OBTAINED AT NO COST BY WRITTEN REQUEST MADE BY THE HOLDER OF RECORD HEREOF TO THE SECRETARY OF THE COMPANY AT ITS PRINCIPAL EXECUTIVE OFFICES. 
  

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 (iii) The Company agrees to remove promptly, upon the request of the holder of this
Warrant and Securities issuable upon exercise of the Warrant, the legend set forth in Section 7(e)(ii) above from the documents/certificates for such securities upon full compliance with this Agreement and Rules 144 and 145. 
 8. Reservation of Stock. The Company covenants that during the term this Warrant is exercisable, the Company will reserve from its authorized and
unissued Common Stock a sufficient number of shares to provide for the issuance of Common Stock upon the exercise of this Warrant and, from time to time, will take all steps necessary to amend its Restated Certificate of Incorporation (the
“Restated Certificate”) to provide sufficient reserves of shares of Common Stock issuable upon exercise of the Warrant. The Company further covenants that all shares that may be issued upon the exercise of rights represented
by this Warrant, upon exercise of the rights represented by this Warrant and payment of the Exercise Price, all as set forth herein, will be free from all taxes, liens and charges in respect of the issue thereof (other than taxes in respect of any
transfer occurring contemporaneously or otherwise specified herein). 
 9. Notices. 
 (a) Whenever the Exercise Price or number of shares purchasable hereunder shall be adjusted pursuant to Section 11 hereof, the Company shall issue a
certificate signed by its Chief Financial Officer setting forth, in reasonable detail, the event requiring the adjustment, the amount of the adjustment, the method by which such adjustment was calculated, and the Exercise Price and number of shares
purchasable hereunder after giving effect to such adjustment, and shall cause a copy of such certificate to be mailed (by first-class mail, postage prepaid) to the Holder of this Warrant. 
 (b) In case: 
 (i) the
Company shall take a record of the holders of its Common Stock (or other stock or securities at the time receivable upon the exercise of this Warrant) for the purpose of entitling them to receive any dividend or other distribution, or any right to
subscribe for or purchase any shares of stock of any class or any other securities, or to receive any other right; 
 (ii) of
any capital reorganization of the Company, any reclassification of the capital stock of the Company, any consolidation or merger of the Company with or into another corporation, or any conveyance of all or substantially all of the assets of the
Company to another corporation; 
 (iii) of any voluntary dissolution, liquidation or winding-up of the Company; or

 (iv) of any redemption or conversion of all outstanding Common Stock; 
 then, and in each such case, the Company will mail or cause to be mailed to the Holder or Holders a notice specifying, as the case may be, (A) the date on which a
record is to be taken for the purpose of such dividend, distribution or right, and stating the amount and character of such dividend, distribution or right, or (B) the date on which such reorganization, reclassification, 

  

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consolidation, merger, conveyance, dissolution, liquidation, winding-up, redemption or conversion is to take place, and the time, if any is to be fixed, as
of which the holders of record of Common Stock (or such stock or securities at the time receivable upon the exercise of this Warrant) shall be entitled to exchange their shares of Common Stock (or such other stock or securities) for securities or
other property deliverable upon such reorganization, reclassification, consolidation, merger, conveyance, dissolution, liquidation or winding-up. Such notice shall be mailed at least fifteen (15) days prior to the date therein specified.

 (c) All such notices, advices and communications shall be deemed to have been received in accordance with Section 9.7 of the Purchase
Agreement. 
 10. 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. 
 11.
Adjustments. The Exercise Price and the number of shares purchasable hereunder are subject to adjustment from time to time as follows: 
 (a) Reclassification, etc. If the Company, at any time while this Warrant, or any portion thereof, remains outstanding and unexpired by reclassification of securities or otherwise, shall change any of the securities as to which
purchase rights under this Warrant exist into the same or a different number of securities of any other class or classes, this Warrant shall thereafter represent the right to acquire such number and kind of securities as would have been issuable as
the result of such change with respect to the securities that were subject to the purchase rights under this Warrant immediately prior to such reclassification or other change and the Exercise Price therefor shall be appropriately adjusted, all
subject to further adjustment as provided in this Section 11. 
 (b) Split, Subdivision or Combination of Shares. If the Company
at any time while this Warrant, or any portion thereof, remains outstanding and unexpired shall split, subdivide or combine the securities as to which purchase rights under this Warrant exist, into a different number of securities of the same class,
then (i) in the case of a split or subdivision, the Exercise Price for such securities shall be proportionately decreased and the securities issuable upon exercise of this Warrant shall be proportionately increased, and (ii) in the case of
a combination, the Exercise Price for such securities shall be proportionately increased and the securities issuable upon exercise of this Warrant shall be proportionately decreased. 
 (c) Adjustments for Dividends in Stock or Other Securities or Property. If while this Warrant, or any portion hereof, remains outstanding and
unexpired the holders of the securities as to which purchase rights under this Warrant exist at the time shall have received, or, on or after the record date fixed for the determination of eligible stockholders, shall have become entitled to
receive, without payment therefor, other or additional stock or other securities or property (other than cash) of the Company by way of dividend, then and in each case, this Warrant shall represent the right to acquire, in addition to the number of
shares of the security receivable upon exercise of this Warrant, and without payment of any additional consideration therefor, the amount of such other or additional stock or other securities or property (other than cash) of the Company that such
holder would hold on the date of such exercise had it been the 

  

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holder of record of the security receivable upon exercise of this Warrant on the date hereof and had thereafter, during the period from the date hereof to
and including the date of such exercise, retained such shares and/or all other additional stock available by it as aforesaid during such period, giving effect to all adjustments called for during such period by the provisions of this
Section 11. 
 (d) Certificate as to Adjustments. Upon the occurrence of each adjustment or readjustment pursuant to this
Section 11, the Company at its expense shall promptly compute such adjustment or readjustment in accordance with the terms hereof and furnish to each Holder of this Warrant a certificate setting forth such adjustment or readjustment and showing
in detail the facts upon which such adjustment or readjustment is based. The Company shall, upon the written request, at any time, of any such Holder, furnish or cause to be furnished to such Holder a like certificate setting forth: (i) such
adjustments and readjustments; (ii) the Exercise Price at the time in effect; and (iii) the number of shares and the amount, if any, of other property that at the time would be received upon the exercise of the Warrant. 
 (e) No Impairment. The Company will not, by any voluntary action, avoid or seek to avoid the observance or performance of any of the terms to be
observed or performed hereunder by the Company, but will at all times in good faith assist in the carrying out of all the provisions of this Section 11 and in the taking of all such action as may be necessary or appropriate in order to protect
the rights of the Holders of this Warrant against impairment. 
 12. Miscellaneous. 
 (a) This Warrant shall be governed by the laws of the State of California as applied to agreements entered into in the State of California by and among
residents of the State of California. 
 (b) In the event of a dispute with regard to the interpretation of this Warrant, the prevailing
party may collect the cost of attorneys’ fees, litigation expenses or such other expenses as may be incurred in the enforcement of the prevailing party’s rights hereunder. 
 (c) This Warrant shall be exercisable as provided for herein, except that in the event that the expiration date of this Warrant shall fall on a Saturday,
Sunday and or United States federally recognized holiday, this expiration date for this Warrant shall be extended to 5:00 p.m. Pacific standard time on the business day following such Saturday, Sunday or recognized holiday. 
  

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 IN WITNESS WHEREOF, eGAIN COMMUNICATIONS CORPORATION has caused this Warrant to be executed by its
officers thereunto duly authorized. 
 Dated: June 29, 2007 
  

			
	COMPANY:
	
	eGAIN COMMUNICATIONS CORPORATION
		
	By	 	 /s/ Eric Smit

	Its:	 	Eric Smit
	Title:	 	Chief Financial Officer


  

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 NOTICE OF EXERCISE 
 To: eGAIN COMMUNICATIONS CORPORATION 
 (1) The undersigned hereby elects to purchase
                     shares of Common Stock of eGAIN COMMUNICATIONS CORPORATION, pursuant to the terms of the attached Warrant, and tenders
herewith payment of the purchase price for such shares in full. 
 (2) In exercising this Warrant, the undersigned hereby confirms and
acknowledges that the shares of Common Stock to be issued upon exercise hereof are being acquired solely for the account of the undersigned and not as a nominee for any other party, or for investment, and that the undersigned will not offer, sell or
otherwise dispose of any such shares of Common Stock except under circumstances that will not result in a violation of the Securities Act of 1933, as amended, or any applicable state securities laws. 
 (3) Please issue a certificate or certificates representing said shares of Common Stock in the name of the undersigned or in such other name as is
specified below: 
  

					
		 		 	  

		 		 	(Name)
			
		 		 	  

		 		 	(Name)
	
	 (4) Please issue a new Warrant for the unexercised portion of the attached Warrant in the name of the undersigned or
in such other name as is specified below:
  

		 		 	  

		 		 	(Name)
			
	  
	 		 	  

	 (Date)
	 		 	(Signature)

  

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 ASSIGNMENT FORM 
 FOR VALUE RECEIVED, the undersigned registered owner of this Warrant hereby sells, assigns and transfers unto the Assignee named below all of the rights of the under¬signed under the within Warrant, with respect
to the number of shares of Common Stock set forth below: 
  

					
	 Name of Assignee
	  	Address	  	No. of Shares
		  		  	
		  		  	
		  		  	
		  		  	

 and does hereby irrevocably constitute and appoint Attorney
                                 to make such transfer on the books of eGAIN
COMMUNICATIONS CORPORATION, maintained for the purpose, with full power of substitution in the premises. 
 The undersigned also represents
that, by assignment hereof, the Assignee acknowledges that this Warrant and the shares of stock to be issued upon exercise hereof or conversion thereof are being acquired for investment and that the Assignee will not offer, sell or otherwise dispose
of this Warrant or any shares of stock to be issued upon exercise hereof or conversion thereof except under circumstances which will not result in a violation of the Securities Act of 1933, as amended, or any applicable state securities laws.
Further, the Assignee has acknowledged that upon exercise of this Warrant, the Assignee shall, if requested by the Company, confirm in writing, in a form satisfactory to the Company, that the shares of stock so purchased are being acquired for
investment and not with a view toward distribution or resale. 
 Dated:
                                 
  

	
	  

	Signature of Holder


  

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