EX-4.1



 Exhibit 4.1 

AMENDMENT NO. 1 TO 
 AMENDED AND
RESTATED INVESTORS’ RIGHTS AGREEMENT 
 THIS AMENDMENT NO. 1, dated as of October 13, 2015 (this
“Amendment”), to the Amended and Restated Investors’ Rights Agreement, dated as of December 9, 2014, (the “Investors’ Rights Agreement”), by and among Rapid7, Inc., a Delaware
corporation (the “Company”), the Investors (as defined therein) and the Other Holders (as defined therein, and including the Linda Holders identified on the signature pages to the Joinder Agreement to the Amended and Restated
Investors’ Rights Agreement dated on or about the date hereof and listed on Schedule C hereto). Capitalized terms used in this Amendment and not otherwise defined herein shall have the meanings ascribed to such terms in the Investors’
Rights Agreement. 
 RECITALS: 

WHEREAS, certain of the Other Holders (such Other Holders listed on Schedule C hereto, the “Linda
Holders”) will become entitled to receive shares of Common Stock in connection with that certain Agreement and Plan of Merger and Reorganization, by and among the Company, Rapid7 LLC, a Delaware limited liability company
(“Acquiror”) and wholly owned subsidiary of the Company, Linda Merger Sub, Inc., a Delaware corporation and wholly owned subsidiary of Acquiror, RevelOps, Inc., a Delaware corporation, and Shareholder Representative Services
LLC, a Colorado limited liability company, solely in its capacity as representative of the Company Securityholders, dated on or about the date hereof (the “Linda Merger Agreement”); 

WHEREAS, the Investors hold shares of the Company’s Common Stock and possess certain rights to cause the Company to register
shares of Common Stock held by or issuable to the Investors; 
 WHEREAS, the Company and the Investors desire for the transactions
contemplated by the Linda Merger Agreement to be consummated and wish to amend the Investors’ Rights Agreement in order to provide the Linda Holders with certain registration rights; 

WHEREAS, the Investors’ Rights Agreement includes a definition of “Required Holders” to mean holders of a majority of
the Series A Preferred Stock and Series B Preferred Stock, voting as a single class on an as-converted basis and (ii) holders of a majority of the Series C Preferred Stock, voting as a single class; 

WHEREAS, in connection with the Company’s initial public offering, all of the Company’s outstanding shares of Preferred Stock
were converted into Common Stock; 
 WHEREAS, Section 6.6 of the Investors’ Rights Agreement provides that the
Investors’ Rights Agreement may be amended or waived only upon the written consent of the Company, the Required Holders and the holders of at least a majority of the then-outstanding Registrable Securities (together with the Required Holders,
the “Requisite Holders”); and 
 WHEREAS, the undersigned Investors hold at least a majority of the
outstanding Registrable Securities. 







 NOW, THEREFORE, for good and valuable consideration, the receipt and sufficiency of which
are hereby acknowledged, and in consideration of the agreements herein, the parties hereto agree as follows: 
 1. Definition
of Linda Holders. The definition of “Linda Holders” shall be inserted in Section 1 of the Investors’ Rights Agreement reading in its entirety as follows: 

“Linda Holders” means each of the stockholders of the Company listed on Schedule C hereto. 

2. Definition of Linda Registrable Securities. The definition of “Linda Registrable Securities” in the Investors’
Rights Agreement shall be inserted in Section 1 of the Investors’ Rights Agreement reading in its entirety as follows: 

“Linda Registrable Securities” means any shares of Common Stock issued to Linda Holders under that certain Agreement and Plan
of Merger and Reorganization (the “Merger Agreement”), by and among the Company, Rapid7 LLC, a Delaware limited liability company (“Acquiror”) and wholly owned subsidiary of the Company, Linda Merger
Sub, Inc., a Delaware corporation and wholly owned subsidiary of Acquiror, RevelOps, Inc., a Delaware corporation, and Shareholder Representative Services LLC, a Colorado limited liability company, solely in its capacity as representative of the
Company Securityholders (as defined in the Merger Agreement), dated as of October 9, 2015. 
 3. Definition of Other
Holder. The definition of “Other Holder” set forth in the preamble to the Investors’ Rights Agreement shall be deleted and a new definition of “Other Holder” shall be inserted in Section 1 of the Investors’
Rights Agreement reading in its entirety as follows: 
 “Other Holder” means such Persons as are identified on Schedule B
and Schedule C hereto. 
 4. Definition of Other Holder Registrable Securities. The definition of “Other Holder
Registrable Securities” set forth in Section 1 shall be amended and restated in its entirety as follows: 
 “Other Holder
Registrable Securities” means (i) the Common Stock issuable or issued upon conversion of the Preferred Stock held by the Other Holders listed on Schedule B, (ii) any Common Stock, or any Common Stock issued or issuable (directly
or indirectly) upon conversion and/or exercise of any other securities of the Company, held or acquired by the Other Holders listed on Schedule B; (iii) the Linda Registrable Securities, and (iv) any Common Stock issued as (or issuable
upon the conversion or exercise of any warrant, right, or other security that is issued as) a dividend or other distribution with respect to, or in exchange for or in replacement of, the shares referenced in clauses (i) - (iii) above; excluding
in all cases, however, any Registrable Securities sold by a Person in a transaction in which the applicable rights under this Agreement are not assigned pursuant to Section 6.1, and excluding for purposes of Section 2 any shares for which
registration rights have terminated pursuant to Section 2.13 of this Agreement. 

  
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 5. Definition of Required Holders. The definition of “Required Holders”
set forth in Section 1 shall be amended and restated in its entirety as follows: 
 “Required Holders” means the
holders of at least two-thirds (2/3) of the Investor Registrable Securities. 
 6. Schedule C. A new Schedule C in
the form attached hereto as Schedule C shall be attached to the Investors’ Rights Agreement and incorporated by reference therein. 

7. Removal of Section 6.9. Section 6.9 of the Investors’ Rights Agreement and all references thereto throughout
the Investors’ Rights Agreement shall be deleted in their entirety. 
 8. Defined Terms. Capitalized terms used but not
defined herein shall have the meaning set forth in the Investors’ Rights Agreement. 
 9. Notices. The second sentence of
Section 6.5 is amended and restated as follows: “If to an Other Holder or Investor (other than a Bain Holder or a TCV Holder) at its address set forth on Schedule A, Schedule B or Schedule C hereto.” 

10. No Other Amendment. Except as expressly amended hereby, the Investors’ Rights Agreement shall remain in full force and
effect in accordance with its terms, without any waiver, amendment or modification of any provision thereof. All references in the Investors’ Rights Agreement to “this Agreement” shall be deemed to refer to the Amended Rights
Agreement. 
 11. Governing Law; Jurisdiction. This Amendment shall be governed by the internal law of the State of Delaware
without giving effect to any choice of law or conflict of law rules or provisions that would cause the application of the laws of any jurisdiction other than the State of Delaware. 

12. Section and Paragraph Headings. The section and paragraph headings in this Amendment are for reference purposes only and
shall not affect the meaning or interpretation of this Amendment. 
 13. Counterparts. This Amendment may be executed in
counterparts, each of which shall be deemed an original, but all of which shall constitute the same instrument. 
 [REMAINDER OF PAGE
INTENTIONALLY LEFT BLANK] 

  
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 IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be executed as of the
date first above written. 
  

			
	RAPID7, INC.
		
	By:	 	/s/ Steven Gatoff
	Name:	 	Steven Gatoff
	Title:	 	Treasurer and CFO


 [Signature Page to Amendment No. 1 to Amended and Restated Investors’ Rights Agreement]








 IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be executed as of the
date first above written. 
  

			
	INVESTORS:
	
	TCV VII, L.P.
	
	By: Technology Crossover Management VII, L.P.
	Its: General Partner
	
	By: Technology Crossover Management VII, Ltd.
	Its: General Partner
		
	By:	 	/s/ Frederic D. Fenton
	Name: Frederic D. Fenton
	Title: Authorized Signatory
	
	TCV VII (A), L.P.
	
	By: Technology Crossover Management VII, L.P.
	Its: General Partner
	
	By: Technology Crossover Management VII, Ltd.
	Its: General Partner
		
	By:	 	/s/ Frederic D. Fenton
	Name: Frederic D. Fenton
	Title: Authorized Signatory
	
	TCV MEMBER FUND, L.P.
	
	By: Technology Crossover Management VII, Ltd.
	Its: General Partner
		
	By:	 	/s/ Frederic D. Fenton
	Name: Frederic D. Fenton
	Title: Authorized Signatory


 [Signature Page to Amendment No. 1 to Amended and Restated Investors’ Rights Agreement]








 IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be executed as of the
date first above written. 
  

			
	INVESTORS:
	
	BAIN CAPITAL VENTURE FUND 2007, L.P.
	
	By: Bain Capital Venture Partners, L.P.
	Its: General Partner
	
	By: Bain Capital Investors, LLC
	Its: General Partner
		
	By:	 	/s/ J. Benjamin Nye
	Name: J. Benjamin Nye
	Title: Authorized Person
	
	BCIP VENTURE ASSOCIATES
	
	By: Bain Capital Investors, LLC
	Its: Managing Partner
	
	By: Bain Capital Venture Investors, LLC
	Its: Attorney-in-fact
		
	By:	 	/s/ J. Benjamin Nye
	Name: J. Benjamin Nye
	Title: Authorized Person
	
	BCIP VENTURE ASSOCIATES - B
	
	By: Bain Capital Investors, LLC
	Its: Managing Partner
	
	By: Bain Capital Venture Investors, LLC
	Its: Attorney-in-fact
		
	By:	 	/s/ J. Benjamin Nye
	Name: J. Benjamin Nye
	Title: Authorized Person


 [Signature Page to Amendment No. 1 to Amended and Restated Investors’ Rights Agreement]








 SCHEDULE C 

Linda Holders added as Other Holders 

Name and Address 
 Polaris Venture Partners
Founders’ Fund VI, L.P. 
 1 Marina Park Drive 

Boston, MA 02110 
 Polaris Venture Partners VI, L.P. 

1 Marina Park Drive 
 Boston, MA 02110 

Two Double Top Limited 
 111 Delwood Walk 

Castleknock, Dublin 15, D15 W8CC 
 FloodgateFund IV, L.P.

 820 Ramona Street, Suite 200 
 Palo Alto, CA 94301 

The Frontline Venture Fund I Limited Partnership 
 26-28
Lombard Street East 
 Dublin 2, Ireland 
 RRE Ventures V,
LP 
 130 East 59th Street, 17th Floor 
 New York, NY 10022

 University College Dublin 
 Belfield 

Dublin 4, Ireland 
 Doug McNary 

450 Artisan Way 
 Somerville, MA 02145