Document:

EX-10.5

 Exhibit 10.5 
 THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE SOLD, PLEDGED OR OTHERWISE TRANSFERRED EXCEPT IN ACCORDANCE WITH
APPLICABLE LAW. 
 WARRANT TO PURCHASE STOCK 

 

			
	Corporation:	  	CHANNELADVISOR CORPORATION, a Delaware corporation
	Number of Shares:	  	36,496 (Subject to Section 1.8)
	Class of Stock:	  	Series C Preferred Stock
	Initial Exercise Price:	  	$0.685 per share
	Issue Date:	  	September 7, 2007
	Expiration Date:	  	September 7, 2014

 THIS WARRANT CERTIFIES
THAT, for good and valuable consideration, the receipt of which is hereby acknowledged, SQUARE 1 BANK or its assignee (“Holder”) is
entitled to purchase the number of fully paid and nonassessable shares of the class of securities (the “Shares”) of CHANNELADVISOR 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 1.4. 

1.3 Intentionally Omitted. 
 1.4 Fair Market Value. If the Company’s common stock is traded in a public market and the Shares are common stock, the fair market value of the Shares shall be the closing price of the Shares
reported for the business day immediately before Holder delivers its Notice of Exercise to the Company (or in the instance where the Warrant is exercised immediately prior to the effectiveness of the Company’s initial public offering, the
“price to public” per share price specified in the final prospectus relating to such offering). If the Company’s common stock is traded in a public market and the Shares are preferred stock, the fair market value of a Share shall be
the closing price of a share of the Company’s common stock reported for the business day immediately before Holder delivers its Notice of Exercise to the Company (or, in the instance where the Warrant is exercised immediately prior to the
effectiveness of the Company’s initial public offering, the initial “price to public” per share price specified in the final prospectus relating to such offering), in both cases, multiplied by the number of shares of the
Company’s common stock into which a Share is convertible. 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. 

1.5 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. 

  
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 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. 
 1.7 Repurchase on Sale, Merger, or Consolidation of the Company. 
 1.7.1
“Acquisition.” For the purpose of this warrant, “Acquisition” means (a) any sale, license, or other disposition of all or substantially all of the assets (including intellectual property) of the Company,
(b) any sale or disposition of all or substantially all of the capital stock of the Company, or (c) any reorganization, consolidation, merger or sale of the voting securities of the Company or any other transaction where the holders of the
Company’s securities before the transaction beneficially own less than 50% of the outstanding voting securities of the surviving entity after the transaction. 
 1.7.2 Assumption of Warrant. If upon the closing of any Acquisition the successor entity assumes 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. The Company shall use reasonable efforts to cause the surviving corporation to assume the obligations of this warrant. 
 1.7.3 Nonassumption. If upon the closing of any Acquisition the successor entity does not assume the obligations of this warrant and Holder has not otherwise exercised this warrant in full, then
this warrant shall be deemed to have been automatically converted pursuant to Section 1.2 and thereafter Holder shall participate in the Acquisition on the same terms as other holders of the same class of securities of the Company. 

1.8 Adjustment in Underlying Number of Shares. The Number of Shares for which this warrant is exercisable shall, depending upon
the amount of Advances requested by Borrower under (and as defined in) that certain Loan and Security Agreement by and between the Company and Square 1 Bank dated as of September 7, 2007, automatically be adjusted to instead be exercisable for an
additional (x) 36,496 for Advances greater than $2,500,000 but less than or equal to $5,000,000; and (y) 36,496 for Advances greater than $5,000,000 but less than or equal to $7,500,000; and (z) 36,496 for Advances greater than
$7,500,000. Any adjustments made to the Number of Shares pursuant to this Section 1.8 shall be in addition to any adjustments made pursuant to Article 2, below. 
 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. Such an event shall include any automatic conversion of the outstanding or issuable securities of
the Company of the same class or series as the Shares to common stock pursuant to the terms of the Company’s Certificate of Incorporation upon the closing of a registered public offering of the Company’s common stock or as otherwise
provided in the Company’s Certificate of Incorporation. 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 

  
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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 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. 

2.4 Adjustments for Diluting Issuances. In the event of the issuance (a “Diluting Issuance”) by the Company after the
Issue Date of securities at a price per share less than the Warrant Price, then the number of shares of common stock issuable upon conversion of the Shares shall be adjusted in accordance with those provisions of the Company’s Certificate of
Incorporation that apply to Diluting Issuances. 
 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. 
 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 the 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 the per share price paid in Company’s most recent equity financing. 

(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 in all material respects as of the Issue Date. 
 3.2 Notice of Certain Events. The Company shall provide Holder
with not less than 10 days prior written notice, including a description of the material facts surrounding, any of the following events: (a) declaration of 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) offering for subscription pro rata to the holders of any class or series of its stock any additional shares of stock of any class or series or other rights; (c) effecting any
reclassification or recapitalization of common stock; or (d) the merger or consolidation with or into any other corporation, or sale, lease, license, or conveyance of all or substantially all of its assets, or liquidation, dissolution or
winding up. 
 3.3 Information Rights. So long as the Holder holds this Warrant, the Company shall deliver to the Holder
(a) within one hundred fifty (150) days after the end of each fiscal year of the Company, the annual audited 

  
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financial statements of the Company certified by independent public accountants of recognized standing and (b) 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. 
 3.4 Registration Under
Securities Act of 1933, as amended. The Company agrees that the Shares or, if the Shares are convertible into common stock of the Company, such common stock, shall be “Registrable Securities”, and Holder shall be a “Holder”
for purposes of Sections 2.3, 2.5, 2.6, 2.7, 2.8, 2.9, 2.10, 2.11, 2.12, 2.13 and Section 5 of the Investor Rights Agreement among the Company and other persons dated as of April 26, 2007. 

3.5 Holder Investment Representations. Holder makes the representations to the Company set forth in Exhibit A hereto in
connection with the issuance of this warrant and the Shares (collectively, the “Securities”). 
 3.6
No Stockholder Rights. Except as provided in this warrant, Holder will not have any rights as a stockholder of the Company until the exercise of this warrant. 
 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 as well as any additional legends that the Company and Holder mutually agree upon with respect
to such Shares: 
 THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE SOLD, PLEDGED OR OTHERWISE
TRANSFERRED EXCEPT IN ACCORDANCE WITH APPLICABLE LAW. 
 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. The Company shall not require Holder to provide an opinion of counsel if the transfer is to an affiliate of Holder or if there is no material question as to the availability of current
information as referenced in Rule 144(c), Holder represents that it has complied with Rule 144 (d) and (e) in reasonable detail, the selling broker represents that it has compiled with Rule 144(f), and the Company is provided with a copy
of Holder’s notice of proposed sale. 
 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). No surrender or reissuance
shall be required if the transfer is to an affiliate of Holder. 
 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: 
 Square 1 Bank 
 Attn: Warrant Administrator 

406 Blackwell Street, Suite 240 
 Crowe Building 
 Durham, NC 27701 

  
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 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. 
 [Balance of Page
Intentionally Left Blank] 

  
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 4.8 Governing Law. This warrant shall be governed by and construed in accordance with
the laws of the State of North Carolina, without giving effect to its principles regarding conflicts of law. 
  

			
	CHANNELADVISOR CORPORATION
		
	By:	 	 

		
	Name:	 	 M. Scot Wingo

		
	Title:	 	 CEO

 [Signature Page to Warrant to Purchase Stock] 

 APPENDIX 1 

NOTICE OF EXERCISE 
 1. The undersigned hereby elects to purchase                  shares of the
                 stock of CHANNELADVISOR CORPORATION pursuant to the terms of the attached Warrant, and tenders herewith payment of the purchase price of such shares in
full. 
 1. The undersigned hereby elects to convert the attached Warrant into shares in the manner specified in the
Warrant. This conversion is exercised with respect to                  of the shares covered by the Warrant. 

[Strike paragraph that does not apply.] 
 2. Please issue a certificate or certificates representing said shares in the name of the undersigned or in such other name as is specified below: 

Square 1 Bank 

Attn: Warrant Administrator 
 406 Blackwell Street, Suite 240 
 Crowe Building 

Durham, NC 27701 

3. The undersigned represents it is acquiring the shares solely for its own account and not as a nominee for any other party and
not with a view toward the resale or distribution thereof except in compliance with applicable securities laws. 
  

	
	SQUARE 1 BANK or Registered Assignee
	
	  

	(Signature)
	
	  

	(Date)

 EXHIBIT A 
 INVESTMENT REPRESENTATIONS 
 (a) The undersigned is aware of the Company’s business
affairs and financial condition, and has acquired sufficient information about the Company to reach an informed and knowledgeable decision to acquire the Securities. The undersigned is purchasing the Securities for its own account for investment
purposes only and not with a view towards, or for resale in connection with, any “distribution” thereof for purposes of the Securities Act of 1933, as amended (the “Securities Act”). The undersigned has such knowledge and
experience in financial business matters and the undersigned is capable of evaluating the merits and risks of the purchase of the Securities and of protecting its interests in connection therewith. 

(b) The undersigned understands that the Securities have not been registered under the Securities Act in reliance upon a specific exemption therefrom,
which exemption depends upon, among other things, the bona fide nature of the undersigned’s investment intent as expressed herein. 
 (c)
The undersigned further understands that the Securities must be held indefinitely, and the undersigned must therefore bear the economic risk therewith, unless the Securities are subsequently registered under the Securities Act or unless an exemption
from registration is otherwise available. In addition, the undersigned understands that the certificate evidencing the Securities will be imprinted with a legend which prohibits the transfer of the Securities unless they are registered or such
registration is not required. 
 (d) The undersigned is familiar with the provisions of Rule 144, promulgated pursuant to the Securities Act,
which, in substance, permits limited public resale of “restricted securities” acquired, directly or indirectly, from the issuer thereof, in a non-public offering subject to the satisfaction of certain conditions. 

(e) The Securities may be resold in certain limited circumstances subject to the provisions of Rule 144, which requires, among other things, the
existence of a public market for the Securities, the availability of certain current public information about the Company, the resale occurring not less than one year after a party has purchased and paid for the security to be sold, the sales being
effected through a “broker’s transaction” or in transactions directly with a “market maker” and the number of securities being sold during any three-month period not exceeding specified limitations. 

(f) The undersigned further understands that in the event that all of the applicable requirements of Rule 144 are not satisfied, registration under the
Securities Act, compliance with Regulation A, or some other registration exemption will be required. 
 (g) The undersigned is an
“accredited investor” as defined in Rule 501(a) of Regulation D promulgated under the Securities Act. 

  
 8EX-10.6

 Exhibit 10.6 
 THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE SOLD, PLEDGED OR OTHERWISE TRANSFERRED EXCEPT IN ACCORDANCE WITH
APPLICABLE LAW. 
 WARRANT TO PURCHASE STOCK 

 

					
		 	Corporation:	  	CHANNELADVISOR CORPORATION, a Delaware corporation
		 	Number of Shares:	  	167,883 shares of Series C Preferred Stock or $115,000/Initial Exercise Price in the case of New Preferred (as defined below)
		 	Class of Stock:	  	Series C Preferred Stock; provided that if the Company issues a new Series of Preferred Stock (“New Preferred”) in a bona fide equity financing yielding at least
$3,000,000 gross proceeds to the Company (a “New Financing”), this warrant shall be exercisable for such series of New Preferred in lieu of Series C Preferred Stock.
		 	Initial Exercise Price:	  	$0.685 per share of Series C Preferred Stock or in the case of New Preferred, the price per share paid for such New Preferred in a New Financing.
		 	Issue Date:	  	June 30, 2008
		 	Expiration Date:	  	June 30, 2015

 THIS WARRANT CERTIFIES
THAT, for good and valuable consideration, the receipt of which is hereby acknowledged, SQUARE 1 BANK or its assignee (“Holder”) is
entitled to purchase the number of fully paid and nonassessable shares of the class of securities (the “Shares”) of CHANNELADVISOR 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 1.4. 

1.3 Intentionally Omitted. 
 1.4 Fair Market Value. If the Company’s common stock is traded in a public market and the Shares are common stock, the fair market value of the Shares shall be the closing price of the Shares
reported for the business day immediately before Holder delivers its Notice of Exercise to the Company (or in the instance where the Warrant is exercised immediately prior to the effectiveness of the Company’s initial public offering, the
“price to public” per share price specified in the final prospectus relating to such offering). If the Company’s common stock is traded in a public market and the Shares are preferred stock, the fair market value of a Share shall be
the closing price of a share of the Company’s common stock reported for the business day immediately before Holder delivers its Notice of Exercise to the Company (or, in the instance where the Warrant is exercised immediately prior to the
effectiveness of the Company’s initial public offering, the initial “price to public” per share price specified in the final prospectus relating to such offering), in both cases, multiplied by the number of shares of the
Company’s common stock into which a Share is convertible. 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	  	

 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. 
 1.7 Repurchase
on Sale, Merger, or Consolidation of the Company. 
 1.7.1 “Acquisition.” For the purpose of this
warrant, “Acquisition” means (a) any sale, license, or other disposition of all or substantially all of the assets (including intellectual property) of the Company, (b) any sale or disposition of all or substantially all of the
capital stock of the Company, or (c) any reorganization, consolidation, merger or sale of the voting securities of the Company or any other transaction where the holders of the Company’s securities before the transaction beneficially own
less than 50% of the outstanding voting securities of the surviving entity after the transaction. 
 1.7.2 Assumption of
Warrant. If upon the closing of any Acquisition the successor entity assumes 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. The Company shall use reasonable efforts to cause
the surviving corporation to assume the obligations of this warrant. 
 1.7.3 Nonassumption. If upon the closing of any
Acquisition the successor entity does not assume the obligations of this warrant and Holder has not otherwise exercised this warrant in full, then this warrant shall be deemed to have been automatically converted pursuant to Section 1.2 and
thereafter Holder shall participate in the Acquisition on the same terms as other holders of the same class of securities of the Company. 
 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. Such an event shall include any automatic conversion of the outstanding or issuable securities of
the Company of the same class or series as the Shares to common stock pursuant to the terms of the Company’s Certificate of Incorporation upon the closing of a registered public offering of the Company’s common stock or as otherwise
provided in the Company’s Certificate of Incorporation. 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	  	

 2.3 Adjustments for 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. 
 2.4 Adjustments for Diluting Issuances. In the event of
the issuance (a “Diluting Issuance”) by the Company after the Issue Date of securities at a price per share less than the Warrant Price, then the number of shares of common stock issuable upon conversion of the Shares shall be adjusted in
accordance with those provisions of the Company’s Certificate of Incorporation that apply to Diluting Issuances. 
 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.

 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 the
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 the per share price paid in Company’s most recent equity financing. 

(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. The Company shall provide Holder with not less than 10
days prior written notice, including a description of the material facts surrounding, any of the following events: (a) declaration of 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) offering for subscription pro rata to the holders of any class or series of its stock any additional shares of stock of any class or series or other rights; (c) effecting any reclassification or
recapitalization of common stock; or (d) the merger or consolidation with or into any other corporation, or sale, lease, license, or conveyance of all or substantially all of its assets, or liquidation, dissolution or winding up. 

3.3 Information Rights. So long as the Holder holds this Warrant, the Company shall deliver to the Holder (a) within one
hundred fifty (150) 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 (b) 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. 

  

					
	

	  	3	  	

 3.4 Registration Under Securities Act of 1933, as amended. The Company agrees that
the Shares or, if the Shares are convertible into common stock of the Company, such common stock, shall be “Registrable Securities”, and Holder shall be a “Holder” for purposes of Sections 2.3, 2.5, 2.6, 2.7, 2.8, 2.9, 2.10,
2.11, 2.12, 2.13 and Section 5 of the Third Amended and Restated Investor Rights Agreement among the Company and other persons dated as of April 26, 2007. 
 3.5 Holder Investment Representations. Holder makes the representations to the Company set forth in Exhibit A hereof in connection with the issuance of this warrant and the Shares (collectively,
the “Securities”). 
 3.6 No Stockholder Rights. Except as provided in this warrant, Holder will not have any
rights as a stockholder of the Company until the exercise of this warrant. 
 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 as well as any additional legends that the Company and Holder mutually agree upon with respect to such Shares: 

THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE SOLD, PLEDGED OR OTHERWISE TRANSFERRED EXCEPT IN
ACCORDANCE WITH APPLICABLE LAW. 
 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. The Company shall not require Holder to provide an opinion of counsel if the transfer is to an affiliate of Holder or if there is no material question as to the availability of current information as referenced in
Rule 144(c), Holder represents that it has complied with Rule 144 (d) and (e) in reasonable detail, the selling broker represents that it has compiled with Rule 144(f), and the Company is provided with a copy of Holder’s notice of
proposed sale. 
 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). No surrender or reissuance shall be required if the transfer
is to an affiliate of Holder. 
 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: 
 Square 1 Bank

 Attn: Warrant Administrator 
 406 Blackwell Street, Suite 240 
 Crowe Building 

Durham, NC 27701 

  

					
	

	  	4	  	

 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. 
 [Balance of Page
Intentionally Left Blank] 

  

					
	

	  	5	  	

 4.8 Governing Law. This warrant shall be governed by and construed in accordance with
the laws of the State of North Carolina, without giving effect to its principles regarding conflicts of law. 
  

			
	CHANNELADVISOR CORPORATION
		
	By:	 	 /s/ M. Scot Wingo

		
	Name:	 	 M. Scot Wingo

		
	Title:	 	 CEO

 [Signature Page to Warrant to Purchase Stock] 

  
 

 

 APPENDIX 1 

NOTICE OF EXERCISE 
 1. The undersigned hereby elects to purchase                  shares of the
                 stock of CHANNELADVISOR CORPORATION pursuant to the terms of the attached Warrant, and tenders herewith payment of the purchase price of such shares in
full. 
 1. The undersigned hereby elects to convert the attached Warrant into shares in the manner specified in the
Warrant. This conversion is exercised with respect to                  of the shares covered by the Warrant. 

[Strike paragraph that does not apply.] 
 2. Please issue a certificate or certificates representing said shares in the name of the undersigned or in such other name as is specified below: 

Square 1 Bank 

Attn: Warrant Administrator 
 406 Blackwell Street, Suite 240 
 Crowe Building 

Durham, NC 27701 

3. The undersigned represents it is acquiring the shares solely for its own account and not as a nominee for any other party and
not with a view toward the resale or distribution thereof except in compliance with applicable securities laws. 
  

	
	SQUARE 1 BANK or Registered Assignee
	
	  

	(Signature)
	
	  

	(Date)

  
 

 

 EXHIBIT A 
 INVESTMENT REPRESENTATIONS 
 (a) The undersigned is aware of the Company’s business
affairs and financial condition, and has acquired sufficient information about the Company to reach an informed and knowledgeable decision to acquire the Securities. The undersigned is purchasing the Securities for its own account for investment
purposes only, not as a nominee or agent, and not with a view towards, or for resale in connection with, any “distribution” thereof for purposes of the Securities Act of 1933, as amended (the “Securities Act”). The undersigned
has such knowledge and experience in financial business matters and the undersigned is capable of evaluating the merits and risks of the purchase of the Securities and of protecting its interests in connection therewith. 

(b) The undersigned understands that the Securities have not been registered under the Securities Act in reliance upon a specific exemption therefrom,
which exemption depends upon, among other things, the bona fide nature of the undersigned’s investment intent as expressed herein. 
 (c)
The undersigned further understands that the Securities must be held indefinitely, and the undersigned must therefore bear the economic risk therewith, unless the Securities are subsequently registered under the Securities Act or unless an exemption
from registration is otherwise available. In addition, the undersigned understands that the certificate evidencing the Securities will be imprinted with a legend which prohibits the transfer of the Securities unless they are registered or such
registration is not required. 
 (d) The undersigned is familiar with the provisions of Rule 144, promulgated pursuant to the Securities Act,
which, in substance, permits limited public resale of “restricted securities” acquired, directly or indirectly, from the issuer thereof, in a non-public offering subject to the satisfaction of certain conditions. 

(e) The Securities may be resold in certain limited circumstances subject to the provisions of Rule 144, which requires, among other things, the
existence of a public market for the Securities, the availability of certain current public information about the Company, the resale occurring not less than one year after a party has purchased and paid for the security to be sold, the sales being
effected through a “broker’s transaction” or in transactions directly with a “market maker” and the number of securities being sold during any three-month period not exceeding specified limitations. 

(f) The undersigned further understands that in the event that all of the applicable requirements of Rule 144 are not satisfied, registration under the
Securities Act, compliance with Regulation A, or some other registration exemption will be required. 
 (g) The undersigned is an
“accredited investor” as defined in Rule 501(a) of Regulation D promulgated under the Securities Act.

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