Document:

EX-10.11

 Exhibit 10.11 
  

 
  
 

 
 Rapid7 UK Limited 

June 13, 2013 
 Richard Moseley 

Restrop Farm, Purton, Swindon 
 Wiltshire SN5 4LW 

United Kingdom 
 Dear Richard: 

We are pleased to offer you the position of Vice President of International with Rapid7 UK Limited (the “Company”). 

Your employment shall commence on a date mutually agreed between you and the Company (currently anticipated to be August 27, 2013). No other previous
employment will count as part of your continuous period of employment with the Company. 
 The first 3 months of your employment shall be a probationary
period and your employment may be terminated during this period at any time on one week’s notice or payment in lieu of notice. The Company may, at its discretion, extend the probationary period for up to a further 3 months. During the
probationary period your performance and suitability for continued employment will be monitored. At the end of the probationary period you will be informed in writing if you have successfully completed your probationary period. 

 

	1.	Position, duties and place of work. You shall perform the duties of Vice President of International as commonly associated with this position and other duties reasonably determined from time to time by the
Company consistent with the Company’s stage of development. You will report to Corey Thomas, President and Chief Executive Officer, Rapid7, Inc. As part of your job duties, you will work with the Company’s People Strategy and Finance teams
to design and develop competitive employee compensation and benefits programs to attract and retain international employees, including but not limited to such schemes as family medical and insurance plans, and subject to approval by the Chief
Financial Officer and Chief People Officer of Rapid7, Inc. 

  

	2.	During your employment with the Company, you will devote the whole of your working time and attention and abilities (except for holiday periods and reasonable periods of illness or other incapacity permitted by the
Company’s general employment policies or applicable law) to your duties and the business of the Company. You shall faithfully and diligently perform your duties to the best of your ability and use your best endevours to promote the interests of
the Company. The Company reserves the right to change your position, duties, reporting relationship, work location, job duties, and the Company’s general employment policies and procedures, from time to time in its discretion.

 Your employment relationship with the Company shall also be governed by the general employment policies and practices of the
Company (except that if the terms of this letter differ from or are in conflict with the Company’s general employment policies or practices, this letter will control), and you will be required to abide by the general employment policies and
practices of the Company and to obey the reasonable instructions of the Company and to comply with lawful rules or regulations issued by the Company from time to time. Details of the Company’s rules relating to dismissal, disciplinary action
and grievances (including the person to whom you may apply if you are dissatisfied with the disciplinary decision to dismiss or any grievance outcome) are available from the Chief People Officer. You also agree to comply with all health and safety
guidelines and instructions that the Company may give from time to time, including those relating to working from home. 

  
 

 

  
  

 
  

 It is a condition of this offer that by accepting it or by commencing work under it you will
not be breaching any contractual or other obligation to any current or former employer or other person and, by accepting this offer, you confirm that this condition has been fulfilled. Subject to the remaining provisions of this clause, your normal
place of work will be your home address, which at present is Restrop Farm, Purton, Swindon Wiltshire SN5 4LW. You shall inform the Company as soon as possible if you plan to move house. You confirm that you are not in breach of any covenant or
agreement in working from home. 
 The Company may require you to travel to and work from other locations in the UK and abroad for the proper
performance of your duties. The Company also may require you to travel to Corporate Headquarters in Boston, MA or other Rapid7 offices as necessary for the proper performance of your duties. If the Company requires you to work abroad for a
consecutive period of one month or more, it shall inform you of the terms that will apply during that time. If the Company or the Company establishes an office or otherwise acquires premises in the United Kingdom, the Company may require you to work
from such premises on reasonable notice to you. 
 You are responsible for ensuring the security of confidential information at home. In
particular, you undertake to protect by password any confidential information held on your home computer, lock your computer terminal when left unattended, ensure any wireless network is secure and keep all papers kept in filing cabinets that are
locked when not in use. 
  

	3.	Compensation; Working Time. Your initial base salary will be one hundred fifty thousand pounds (£150.000,00) per annum, less standard payroll deductions and withholdings. Your salary will accrue
daily and you will be paid monthly in arrears in accordance with Company practice and policy directly into your bank or building society. You will be expected to work the Company’s normal business hours (Monday to Friday, 9am to 6pm with one
hour for lunch) and such additional time as may be required by the nature of your work assignments. You will not be eligible for overtime compensation. You agree that for the purposes of the Working Time Regulations 1998 (and any amendment or
re-enactment thereof) any legislative provisions imposing a maximum number of average weekly working hours shall not apply to your employment. You may withdraw your consent by giving the Company not less than three (3) months’ notice in
writing. 

 In addition, you will be eligible to earn a target commission of one hundred fifty thousand pounds
(£150.000,00) annually based on the achievement of targets to be notified to you within 60 days of your Start Date. For exceptional performance, the potential commission will not be capped and it will be possible for you to earn in excess
of that sum in the event that you exceed mutually agreed upon targets. As a condition precedent to earning and receiving your commission, you must remain an active employee with the Company through the date the commission otherwise is scheduled to
be paid. If your employment has been terminated for any reason before such date or if you are working under notice, whether given by you or the Company, then you will not be entitled to any unpaid commission even where such commission has been
notified to you. 
 Your compensation package will be reviewed on an annual or more frequent basis by the Company, and is subject to change
in the discretion of the Company. There is no obligation on the Company to increase your compensation package following a review. 
 The
Company will reimburse you for reasonable expenses incurred in the course of your business duties in accordance with Company’s expense policy and upon submission of appropriate receipts. 

The Company may deduct from your salary, or any other sums owed to you, any money which you owe to the Company or any group company.

  

	4.	Stock Options. 

 Subject to approval of the board of directors of Rapid7, Inc.
(the “Parent”), Parent will issue you an option (the “Option”) to purchase sixty thousand (60.000,00) shares of Parent’s common stock pursuant to the Rapid7 Stock 

  
 

 

  
  

 
  

 Option Plan (the “Plan”) at an exercise price equal to the fair market value
of the stock as of the date of grant as determined by the Parent board. The Option will be subject to a four-year vesting period subject to your continued employment with the Company, with twenty-five percent (25%) of the shares subject to the
Option vesting on the one year anniversary of your vesting commencement date, and one-forty-eighth (1/48th) of the shares subject to the Option vesting for each month of your continued service thereafter. The Option will be governed in full by
the terms and conditions of the Plan and your individual option agreement. The option shall be subject to the standard terms and conditions of the Parent’s executive change of control plan, as approved and amended by the Parent board of
directors. The Option shall not form part of your entitlement to remuneration, benefits or entitlements pursuant to your contract of employment and your contract of employment shall not give you any right to have an option granted to you in respect
of any number of shares either subject to any condition or at all. Your rights and obligations under the terms of your contract of employment shall not be affected by your participation in the Plan. In particular, no benefits under the Plan shall be
pensionable. You shall have no rights to seek equitable relief or to receive compensation or damages for any loss or potential loss which you may suffer in connection with any options or any rights or entitlements granted pursuant to the Plan or any
other employee share plan established by the Company or any other group company which loss or potential loss arises in consequence of the loss or termination of your employment with any group company for any reason whatsoever and however that
termination may be occasioned (including, without limitation, wrongful, unfair or otherwise unlawful termination). 
  

	5.	Benefits. 

  

	 	a.	Pension. The Company shall comply with its legal obligations in relation to the provision of pension arrangements and contributions. At present, the Company is not required to make arrangements for you to
participate in a pension scheme. However, the Company will make a contribution of an amount equivalent to eight per cent (8%) of your basic salary to a personal pension plan for your benefit. A contracting out certificate is not in force in
respect of your employment. 

  

	 	b.	Holidays. You are entitled to twenty-five (25) days paid holiday in addition to the usual public holidays in the UK in each complete year of your employment. You are entitled to a pro rata proportion
of such holiday entitlement in the calendar year of your joining and leaving the Company’s employment. Holidays shall be paid at your normal rate of salary as set out above. You must agree your holiday leave in advance with the Company, subject
to the Company’s operational requirements. Your holiday entitlement will be deemed to accrue from day to day and may not be carried over from one holiday year to the next. The Company reserves the right to require you to take any outstanding
holiday during any period of notice of termination of employment (whether given by you or the Company). No payment will be made in lieu of holiday accrued but not taken, save on termination of your employment. If, upon the termination of employment,
the number of days of holiday which you have taken in the relevant year differs from your accrued entitlement, then a payment for the number of days’ difference will be either paid to you or refunded by you depending on whether the amount
actually taken is less or greater than your entitlement and you hereby consent to the Company making a deduction from your final salary payment and/or other monies owed to you if you have taken more holiday than you have accrued. You will not be
entitled to such a payment if the Company is entitled to, and does terminate your employment summarily or if you refuse to take any holiday entitlement during your notice period. The Company’s holiday year runs from January 1st to
December 31st. 

  

	 	c.	Sickness. You will be entitled to full pay for up to 10 days of absence due to sickness or injury in any consecutive 12 month period. Any further period will be paid as provided for under the statutory
sick pay (“SSP”) legislation in force at the relevant time. Monday to Friday (inclusive) in each week shall be qualifying days for the purposes of legislation relating to SSP. If you are unable to attend work and/or perform your
duties on any day because of sickness or injury, you must notify your supervisor by 9am on that day. 

  
 

 

  
  

 
  

 In the event of sickness or injury which lasts for up to 7 consecutive calendar days, you
shall promptly send a self-certificate to the Company in the form set out by the Company. For absence of more than 7 consecutive calendar days you must obtain a certificate from your doctor (a “Statement of Fitness for Work”) stating that
you are not fit for work and the reason(s) why. This should be forwarded to your supervisor as soon as possible. If your absence continues, further certificates must be provided to cover the whole period of absence until you return to work. Where
the Company is concerned about the reason for absence or frequent short-term absence, it may require a medical certificate for each absence, regardless of the duration. In such circumstances, the Company will cover any costs incurred in obtaining
such medical certificates, for absences of less than a week, on production of a doctor’s invoice. You agree to be examined at the Company’s expense by a doctor nominated by the Company if any time it so requests and you authorize the
doctor to disclose and discuss with the Company and its advisers the results of such examinations. 
 In the event that you are sick during a
period of annual leave, in the event that you wish to reclaim the annual leave, you must provide a medical certificate for each day of your sickness during that period of holiday. In the absence of such a certificate, the Company will consider that
period of annual leave to have been taken from your annual entitlement. 
  

	 	d.	Car allowance. The Company shall provide you a car allowance of ten thousand pounds (£10.000,00) gross per year, which shall be payable at the rate of £833.33 per month, paid with and
in the same manner as the salary in accordance with clause 2 above. 

  

	 	e.	Fuel Card. In addition, the Company shall provide you with a monthly fuel stipend 

  

	 	f.	Other. The Company may modify its benefits programs from time to time in its discretion. 

  

	6.	Proprietary Information and Inventions Agreement. As a condition of employment, you are required to sign and abide by the Company’s Proprietary Information and Inventions Agreement (the
“Proprietary Information Agreement”), a form of which is attached hereto as Attachment A. 

  

	7.	Protection of Third Party Information. In your work for the Company, you shall not use or disclose any confidential information or materials, including trade secrets, of any former employer or other third
party to whom you have an obligation of confidentiality; and not to violate any lawful agreement that you may have with any third party. By signing this letter, you represent that you are able to perform your job duties within these guidelines, and
you are not in unauthorized possession of any confidential documents or other property of any former employer or other third party. In addition, you represent that you have disclosed to the Company in writing any agreement you may have with any
third party (e.g., a former employer) which may limit your ability to perform your duties to the Company, or which otherwise could create a conflict of interest with the Company. 

 

	8.	Outside Activities. Throughout your employment with the Company, you may engage in civic and not-for-profit activities so long as such activities do not interfere with the performance of your duties
hereunder or present a conflict of interest with the Company. Subject to the restrictions set forth herein and with the prior written consent of the Board, you may serve as a director of other corporations and may devote a reasonable amount of your
time to other types of business or public activities not expressly mentioned in this paragraph. The Board may rescind its consent to your service as a director of all other corporations or participation in other business or public activities, if the
Board, in its sole discretion, determines that such activities compromise or threaten to compromise the Company’s business interests or conflict with your duties to the Company. 

During your employment by the Company, except on behalf of the Company, you will not directly or indirectly serve as an officer, director,
stockholder, employee, partner, proprietor, investor, joint venturer, associate, representative or consultant of any other person, corporation, firm, partnership or other entity whatsoever known by you to compete with the Company (or is planning or
preparing to compete with the Company), anywhere in the world, in any line of 

  
 

 

  
  

 
  

 
business engaged in (or planned to be engaged in) by the Company; provided, however, that you may purchase or otherwise acquire up to (but not more than) one percent (1%) of any class of
securities of any enterprise (but without participating in the activities of such enterprise) if such securities are listed on any national or regional securities exchange. 
  

	9.	Termination. Subject to the remaining provisions of this clause, you must give the Company and are entitled to receive from the Company one (1) calendar month’s notice in writing of termination
of employment and to an additional week’s notice for each year of employment in excess of four (4) years up to a maximum of 12 weeks’ notice in writing. 

Notwithstanding the notice provisions set out above in this clause 8, the Company is entitled, at its sole discretion, to terminate your
employment at any time with immediate effect by notifying you that it is exercising its right under this clause. In such circumstances, the Company will make a payment in lieu of basic salary to you in lieu of notice within 28 days of such
notification, deducting such sums equivalent to tax and other withholdings from such payment. The Company is also entitled at its sole discretion to require you to work a proportion of the notice period and to pay you in lieu of the remaining
proportion. If the Company decides not to exercise this right, you cannot enforce the payment as a contractual debt nor as liquidated damages and your sole remedy shall be a claim in damages. 

The Company may terminate your employment with immediate effect in the case of gross misconduct (for example, a material breach of the terms of
your employment, an act of dishonesty or willful neglect) and (after a warning in writing) if you have committed any repeated or continued breach of your obligations to the Company or if you cease to be entitled to work in the UK. 

If written notice to terminate your employment has been given by you or the Company, the Company may require you to perform such alternative
duties as the Company reasonably determines or require you to perform no duties and/or exclude you from the premises. During this period, the Company will be under no obligation to provide any work or vest any powers in you and you will have no
right to perform any services for the Company. In these circumstances, the Company shall continue to pay you at your basic salary referred to above, and provide all other contractual benefits to you. During any such period you will remain employed
by the Company and subject to all your express and implied duties towards the Company. In particular, you agree that you will not carry out work of any kind for a third party. 

Upon termination of your employment under this agreement for any reason whatsoever or at any time on request by the Company you must
immediately return to the Company all items of property belonging to the Company in your possession or control, including but not limited to any items that relate to the intellectual property, affairs and business of the Company, including customer
lists, sale records, technical information and data, software, manuals, correspondence, notes, reports, papers and other documents (together with any summaries, extracts or copies thereof), company care, keys, credit cards, passes and tools. Your
obligations under this clause include the return of property in all formats, including electronic documents. You shall if requested by the Company confirm your compliance with your obligations under this clause in writing. 

If you have any confidential information or work you have carried out for the Company which is stored on a device (including a personal
computer, laptop computer, web-server, personal digital assistant, smart phone, disk, memory stick or other device) which does not belong to the Company, you undertake that you will notify the Company of this fact and provide the Company with access
to such a device so that it can download the information and/or supervise its deletion from the device concerned. 
  

	10.	Proof of Right to Work. This offer of employment is conditional on you providing to the Company documentary evidence of your identity and eligibility for employment in the United Kingdom. Such
documentation must be provided to us within three (3) business days of your Start Date, or our employment relationship with you may be terminated. 

  
 

 

  
  

 
  

	11.	Confidentiality of Terms. You agree to follow the Company’s policy that employees must not disclose, either directly or indirectly, any information, including any of the terms of this offer letter, in
particular regarding salary, bonuses, or stock option allocations to any person, including other employees of the Company or of the Parent; provided, however, that you may discuss such terms with members of your immediate family and
any legal, tax or accounting specialists who provide you with individual legal, tax, or accounting advice. 

  

	12.	Miscellaneous. There is no collective agreement which directly affects your employment. This letter, including the attached Proprietary Information Agreement, constitutes the complete, final and exclusive
embodiment of the entire agreement between you and the Company with regard to the subject matter hereof. It is entered into without reliance on any promise or representation, written or oral, other than those expressly contained herein, and it
supersedes any other agreements, promises, warranties or representations concerning its subject matter. It is not intended that the Contracts (Rights of Third Parties) Act 1999 should apply to this letter or that any third party should be able to
enforce any term of this letter against the Company or any of its group companies. If any provision of this letter agreement is determined to be invalid or unenforceable, in whole or in part, this determination shall not affect any other provision
of this letter agreement and the provision in question shall be modified so as to be rendered enforceable in a manner consistent with the intent of the parties insofar as possible under applicable law. This letter agreement shall be construed and
enforced in accordance with English law without regard to conflicts of law principles and the parties submit to the non-exclusive jurisdiction of the courts of England and Wales. Any ambiguity in this letter agreement shall not be construed against
either party as the drafter. Any waiver of a breach of this letter, or rights hereunder, shall be in writing and shall not be deemed to be a waiver of any successive breach or rights hereunder. This letter may be executed in counterparts which shall
be deemed to be part of one original, and facsimile signatures shall be equivalent to original signatures. 

  

	13.	Expiration of this offer letter. The terms of this offer letter will expire if not accepted by 5pm Pacific Time on June 21, 2013. 

  
 

 

  
  

 
  

 We are all delighted to be able to extend you this offer of employment and look forward to working with you.
To indicate your acceptance of the Company’s offer, please sign and date this offer letter in the space provided below and return it to me, along with a signed and dated copy of the Proprietary Information Agreement. 

 

	
	Very truly yours,
	
	Rapid7 UK Limited
	
	/s/ Corey Thomas
	Corey Thomas
	Director

  

	
	ACCEPTED AND AGREED:
	
	Richard Moseley
	
	 /s/ Richard Moseley

	Signature
	
	 14th June 2013

	Date

 Enclosure: Proprietary Information and Inventions AgreementEX-10.12

 Exhibit 10.12 

SUBORDINATED LOAN AND SECURITY AGREEMENT 

This SUBORDINATED LOAN AND SECURITY AGREEMENT (this “Agreement”) dated as of December 27, 2013 (the
“Effective Date”) is among (a) SILICON VALLEY BANK, a California corporation (“Bank”), and (b) RAPID7, INC., a Delaware corporation (“Inc.”), and RAPID7 LLC, a Delaware
limited liability company (“LLC”) (Inc. and LLC are, jointly and severally, individually and collectively, “Borrower”), and provides the terms on which Bank shall lend to Borrower, and Borrower shall repay Bank. The
parties agree as follows: 
  

	 	1	ACCOUNTING AND OTHER TERMS 

 Accounting terms not defined in this Agreement shall be
construed following GAAP. Calculations and determinations must be made following GAAP; provided that if at any time any change in GAAP would affect the computation of any financial ratio or requirement set forth in any Loan Document, and
either Borrower or Bank shall so request, Borrower and Bank shall negotiate in good faith to amend such ratio or requirement to preserve the original intent thereof in light of such change in GAAP; provided, further, that, until so amended,
(a) such ratio or requirement shall continue to be computed in accordance with GAAP prior to such change therein and (b) Borrower shall provide Bank financial statements and other documents required under this Agreement or as reasonably
requested hereunder setting forth a reconciliation between calculations of such ratio or requirement made before and after giving effect to such change in GAAP. The term “financial statements” includes the notes and schedules. Capitalized
terms not otherwise defined in this Agreement shall have the meanings set forth in Section 13 of this Agreement. All other terms contained in this Agreement, unless otherwise indicated, shall have the meanings provided by the Code to the extent
such terms are defined therein. 
  

	 	2	LOAN AND TERMS OF PAYMENT 

 2.1 Promise to Pay. Borrower hereby unconditionally
promises to pay Bank the outstanding principal amount of all Credit Extensions and accrued and unpaid interest thereon together with any fees as and when due in accordance with this Agreement. 

2.1.1 Mezzanine Term Loan. 

(a) Availability. Subject to the terms and conditions of this Agreement, upon Borrower’s request, during the Draw Period, Bank
shall make up to two (2) term loan advances available to Borrower in an aggregate amount of up to Eighteen Million Dollars ($18,000,000.00) (each, a “Mezzanine Term Loan” and collectively, the “Mezzanine Term
Loans”. Each Mezzanine Term Loan must be in an amount equal to at least Five Million Dollars ($5,000,000.00) (provided that the second Mezzanine Term Loan may be in such amount as is remaining of the commitment after disbursement of the
first Mezzanine Term Loan). After repayment, no Mezzanine Term Loan (or any portion thereof) may be reborrowed. 
 (b) Interest
Period. With respect to each Mezzanine Term Loan, commencing on the first Payment Date of the month following the month in which the Funding Date of such Mezzanine Term Loan occurs, and continuing on each Payment Date thereafter, Borrower shall
make monthly payments of interest, in arrears, on the principal amount of the Mezzanine Term Loan at the rate set forth in Section 2.2(a). 

(c) Repayment. Commencing on the Mezzanine Term Loan Amortization Date, and continuing on each Payment Date thereafter, Borrower shall
repay the Mezzanine Term Loans in (i) twenty-four (24) equal monthly installments of principal, plus (ii) monthly payments of accrued interest at the rate set forth in Section 2.2(a). All outstanding principal and accrued and
unpaid interest under each Mezzanine Term Loan, and all other outstanding Obligations with respect to such Mezzanine Term Loan, are due and payable in full on the Mezzanine Term Loan Maturity Date. 

(d) Permitted Prepayment. Borrower shall have the option to prepay all, but not less than all, of the Mezzanine Term Loans, provided
Borrower (i) delivers written notice to Bank of its election to prepay the Mezzanine Term Loans at least five (5) days prior to such prepayment, and (ii) pays, on the date of such prepayment

  
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(A) all outstanding principal plus accrued and unpaid interest with respect to the portion of the Mezzanine Term Loans being prepaid, (B) the Prepayment Premium, (C) the Final Payment
and (D) all other sums, including Bank Expenses, if any, that shall have become due and payable with respect to the Mezzanine Term Loans, including interest at the Default Rate with respect to any past due amounts. 

(e) Mandatory Prepayment Upon an Acceleration. If the Mezzanine Term Loans are accelerated by Bank following the occurrence and during
the continuance of an Event of Default, Borrower shall immediately pay to Bank an amount equal to the sum of (i) all outstanding principal plus accrued and unpaid interest with respect to the Mezzanine Term Loans, (ii) the Prepayment
Premium, (iii) the Final Payment and (iv) all other sums, including Bank Expenses, if any, that shall have become due and payable hereunder with respect to the Mezzanine Term Loans, including interest at the Default Rate with respect to
any past due amounts. 
 2.2 Payment of Interest on the Credit Extensions. 

(a) Interest Rate. Subject to Section 2.2(b), the principal amount outstanding under each Mezzanine Term Loan shall accrue
interest at a fixed per annum rate equal to twelve percent (12.0%), which interest shall be payable monthly in accordance with Section 2.2(d) below. 

(b) Default Rate. Immediately upon the occurrence and during the continuance of an Event of Default, Obligations shall bear interest at
a rate per annum which is three percent (3.0%) above the rate that would otherwise be applicable thereto (the “Default Rate”). Fees and expenses which are required to be paid by Borrower pursuant to the Loan Documents
(including, without limitation, Bank Expenses) but are not paid when due shall bear interest until paid at a rate equal to the highest rate applicable to the Obligations. Payment or acceptance of the increased interest rate provided in this
Section 2.2(b) is not a permitted alternative to timely payment and shall not constitute a waiver of any Event of Default or otherwise prejudice or limit any rights or remedies of Bank. 

(c) Computation; 360 Day Year. Interest is payable monthly on the first calendar day of each month and shall be computed on the basis
of a 360-day year for the actual number of days elapsed. In computing interest with respect to the Mezzanine Term Loans, the date of the making of any Mezzanine Term Loan shall be included and the date of payment shall be excluded; provided,
however, that if any Mezzanine Term Loan is repaid on the same day on which it is made, such day shall be included in computing interest on such Mezzanine Term Loan. Interest with respect to the Mezzanine Term Loans shall be computed on
the basis of a 360-day year for the actual number of days elapsed. 
 (d) Interest Payment Date. Unless otherwise provided, interest
with respect to the Mezzanine Term Loans is payable monthly on the Payment Date. 
 2.3 Fees. Borrower shall pay to Bank: 

(a) Mezzanine Term Loan Commitment Fee. A fully-earned, non-refundable commitment fee in connection with the Mezzanine Term Loan of One
Hundred Thirty Five Thousand Dollars ($135,000.00), on the Effective Date; 
 (b) Prepayment Premium. The Prepayment Premium, when
due hereunder; 
 (c) Final Payment. For each Mezzanine Term Loan, a payment (in addition to and not a substitution for the regular
monthly payments of principal plus accrued interest) equal to the original principal amount of such Mezzanine Term Loan extended by Bank multiplied by the Final Payment Percentage (each, a “Final Payment”), due on the earliest to
occur of (i) the Mezzanine Term Loan Maturity Date, (ii) the prepayment of a Mezzanine Term Loan, or (iii) the termination of this Agreement; and 

(d) Bank Expenses. All Bank Expenses (including reasonable attorneys’ fees and expenses for documentation and negotiation of this
Agreement) incurred through and after the Effective Date, when due (or, if no stated due date, upon demand by Bank). 

  
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 2.4 Payments; Application of Payments; Debit of Accounts. 

(a) All payments to be made by Borrower under any Loan Document in respect of any Mezzanine Term Loan shall be made in immediately available
funds in Dollars, without setoff or counterclaim, before 3:00 p.m. Eastern time on the date when due. Payments of principal and/or interest received after 3:00 p.m. Eastern time are considered received at the opening of business on the next Business
Day. When a payment is due on a day that is not a Business Day, the payment shall be due the next Business Day, and additional fees or interest, as applicable, shall continue to accrue until paid. 

(b) Bank has the exclusive right to determine the order and manner in which all payments with respect to the Obligations may be applied.
Borrower shall have no right to specify the order or the accounts to which Bank shall allocate or apply any payments required to be made by Borrower to Bank or otherwise received by Bank under this Agreement when any such allocation or application
is not specified elsewhere in this Agreement. 
 (c) Bank may debit any of Borrower’s deposit accounts for payments or any amounts
Borrower owes Bank hereunder. These debits shall not constitute a set-off. 
  

	 	3	CONDITIONS OF LOANS 

 3.1 Conditions Precedent to Initial Credit Extension.
Bank’s obligation to make the initial Credit Extension is subject to the condition precedent that Bank shall have received, in form and substance satisfactory to Bank, such documents, and completion of such other matters, as Bank may reasonably
deem necessary or appropriate, including, without limitation: 
 (a) the Loan Documents; 

(b) the First Loan Modification Agreement with respect to the Senior Loan Agreement; 

(c) the Warrant together with a capitalization table and copies of Borrower’s equity documents; 

(d) the SVB Control Agreement of each Borrower and any other Control Agreement(s) required by Bank; 

(e) Operating Documents of each Borrower and a long form good standing certificate of each Borrower certified by the Secretary of State of the
State of Delaware, as of a date no earlier than thirty (30) days prior to the Effective Date; 
 (f) the completed and executed
Borrowing Resolutions for each Borrower; 
 (g) a secretary’s corporate borrowing certificate and shareholder consent for Inc.; 

(h) a limited liability company borrowing certificate and requisite manager consent for LLC; 

(i) certified copies, dated as of a recent date, of financing statement searches, as Bank shall request, accompanied by written evidence
(including any UCC termination statements) that the Liens indicated in any such financing statements either constitute Permitted Liens or have been terminated or released; 

(j) completed exhibits to the IP Agreement and copies of searches with the United States Patent and Trademark Office and the United States
Copyright Office for each Borrower; 
 (k) the Perfection Certificate of each Borrower, together with the duly executed original signature
thereto; 
 (l) evidence satisfactory to Bank that the insurance policies required by Section 6.4 of this Agreement are in full force
and effect, together with appropriate evidence showing lender loss payable and additional insured clauses and cancellation notice to Bank (including certificates on Acord 25 and Acord 28 forms and endorsements to the policies reflecting the same);

  
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 (m) payment of the fees and Bank Expenses then due as specified in Section 2.3 of this
Agreement; 
 (n) Certificate of Good Standing/Foreign Qualification for Inc. from Massachusetts; and 

(m) Certificates of Good Standing/Foreign Qualification for LLC from California, Massachusetts and Texas. 

3.2 Conditions Precedent to all Credit Extensions. Bank’s agreement to make each Credit Extension, including the initial Credit
Extension, is subject to the following: 
 (a) except as otherwise provided in Section 3.5, timely receipt of an executed
Payment/Advance Form; and 
 (b) each of the representations and warranties in this Agreement shall be true, accurate, and complete in all
material respects on the date of the Payment/Advance Form and on the Funding Date of each Credit Extension and no Event of Default shall have occurred and be continuing, or result from the Credit Extension. Each Credit Extension is Borrower’s
representation and warranty on that date that the representations and warranties in this Agreement remain true, accurate, and complete in all material respects. 

3.3 Suspension of Credit Extensions. Borrower’s ability to request that Bank make Credit Extensions hereunder will terminate if,
in Bank’s sole discretion, there has been a Material Adverse Change, or there has been any material adverse deviation by Borrower from the most recent business plan of Borrower presented to and accepted by Bank prior to the Effective Date. 

3.4 Covenant to Deliver. Borrower agrees to deliver to Bank each item required to be delivered to Bank under this Agreement as a
condition precedent to any Credit Extension. Borrower expressly agrees that a Credit Extension made prior to the receipt by Bank of any such item shall not constitute a waiver by Bank of Borrower’s obligation to deliver such item, and the
making of any Credit Extension in the absence of a required item shall be in Bank’s sole discretion. 
 3.5 Procedures for
Borrowing. Subject to the prior satisfaction of all other applicable conditions to the making of a Mezzanine Term Loan set forth in this Agreement, to obtain a Mezzanine Term Loan, Borrower shall notify Bank (which notice shall be irrevocable)
by electronic mail, facsimile, or telephone by 12:00 p.m. Eastern time two (2) Business Days prior to the requested Funding Date of the Mezzanine Term Loan. Together with any such electronic or facsimile notification, Borrower shall deliver to
Bank by electronic mail or facsimile a completed Payment/Advance Form executed by a Responsible Officer or his or her designee. Bank may rely on any telephone notice given by a person whom Bank believes is a Responsible Officer or designee. Bank
shall credit Mezzanine Term Loans to a deposit account of Borrower maintained with Bank. Bank may make Mezzanine Term Loans under this Agreement based on instructions from a Responsible Officer or his or her designee or without instructions if the
Mezzanine Term Loans are necessary to meet Obligations which have become due. 
  

	 	4	CREATION OF SECURITY INTEREST 

 4.1 Grant of Security Interest. Borrower hereby
grants Bank, to secure the payment and performance in full of all of the Obligations, a continuing security interest in, and pledges to Bank, the Collateral, wherever located, whether now owned or hereafter acquired or arising, and all proceeds and
products thereof. Borrower represents, warrants, and covenants that the security interest granted herein shall be and shall at all times continue to be a first priority perfected security interest in the Collateral subject only to Permitted Liens
that are permitted to have priority over Bank’s Liens hereunder. If Borrower shall at any time acquire a commercial tort claim, Borrower shall promptly notify Bank in a writing signed by Borrower of the general details thereof and grant to Bank
in such writing a security interest therein and in the proceeds thereof, all upon the terms of this Agreement, with such writing to be in form and substance satisfactory to Bank. 

Bank’s security interest in the assets of Borrower securing the Obligations of Borrower to Bank under this Agreement shall be junior and
subordinate to Bank’s security interest in the assets of Borrower securing all other obligations of Borrower to Bank including, without limitation, those under the Senior Loan Agreement. 

  
 4 

 Borrower acknowledges that it may have previously entered, and/or may in the future enter, into
Bank Services with Bank. Regardless of the terms of any Bank Services Agreement, Borrower agrees that any amounts Borrower owes Bank thereunder shall be deemed to be Obligations hereunder and that it is the intent of Borrower and Bank to have all
such Obligations secured by the first priority security interest granted herein (subject only to Permitted Liens that are permitted to have superior priority to Bank’s Lien in this Agreement). 

If this Agreement is terminated, Bank’s Lien in the Collateral shall continue until the Obligations (other than inchoate indemnity
obligations) are satisfied in full, and at such time, Bank shall, at Borrower’s sole cost and expense, terminate its security interest in the Collateral and all rights therein shall revert to Borrower. In the event (a) all Obligations
(other than inchoate indemnity obligations), except for Bank Services, are satisfied in full, and (b) this Agreement is terminated, Bank shall terminate the security interest granted herein upon Borrower providing cash collateral acceptable to
Bank in its good faith business judgment for Bank Services, if any. In the event such Bank Services consist of outstanding Letters of Credit, Borrower shall provide to Bank cash collateral in an amount equal to one hundred five percent
(105%) for Letters of Credit denominated in Dollars and one hundred ten percent (110%) for Letters of Credit denominated in a currency other than Dollars, in each case of the Dollar Equivalent of the face amount of all such Letters of
Credit plus all interest, fees, and costs due or to become due in connection therewith (as estimated by Bank in its good faith business judgment), to secure all of the Obligations relating to such Letters of Credit. 

4.2 Authorization to File Financing Statements. Borrower hereby authorizes Bank to file financing statements, without notice to
Borrower, with all appropriate jurisdictions to perfect or protect Bank’s interest or rights hereunder, including a notice that any disposition of the Collateral, by either Borrower or any other Person, shall be deemed to violate the rights of
Bank under the Code, unless permitted under this Agreement. Any such financing statements may indicate the Collateral as “all assets of the Debtor” or words of similar effect, or as being of an equal or lesser scope, or with greater
detail, all in Bank’s discretion. 
  

	 	5	REPRESENTATIONS AND WARRANTIES 

 Borrower represents and warrants as follows: 

5.1 Due Organization and Authorization. Borrower and each of its Subsidiaries are duly existing and in good standing as Registered
Organizations in their respective jurisdictions of formation and are qualified and licensed to do business and are in good standing in any other jurisdiction in which the conduct of their respective business or ownership of property requires that
they be qualified except where the failure to do so could not reasonably be expected to have a material adverse effect on Borrower’s business. In connection with this Agreement, each Borrower has delivered to Bank a completed certificate signed
by Borrower, entitled Perfection Certificate (the “Perfection Certificate”). Borrower represents and warrants to Bank that (a) Borrower’s exact legal name is that indicated on the Perfection Certificate and on the
signature page hereof; (b) Borrower is an organization of the type and is organized in the jurisdiction set forth in the Perfection Certificate; (c) the Perfection Certificate accurately sets forth Borrower’s organizational
identification number or accurately states that Borrower has none; (d) the Perfection Certificate accurately sets forth Borrower’s place of business, or, if more than one, its chief executive office as well as Borrower’s mailing
address (if different than its chief executive office); (e) Borrower (and each of its predecessors) has not, in the past five (5) years, changed its jurisdiction of formation, corporate structure, organizational type, or any organizational
number assigned by its jurisdiction; and (f) all other information set forth on the Perfection Certificate pertaining to Borrower and each of its Subsidiaries is accurate and complete in all material respects (it being understood and agreed
that Borrower may from time to time update certain information in the Perfection Certificate after the Effective Date to the extent permitted by one or more specific provisions in this Agreement). If Borrower is not now a Registered Organization but
later becomes one, Borrower shall promptly notify Bank of such occurrence and provide Bank with Borrower’s organizational identification number. 

The execution, delivery and performance by Borrower of the Loan Documents to which it is a party have been duly authorized, and do not
(i) conflict with any of Borrower’s organizational documents, (ii) contravene, conflict with, constitute a default under or violate any material Requirement of Law, (iii) contravene, conflict or violate any applicable order,
writ, judgment, injunction, decree, determination or award of any Governmental Authority by which Borrower or any of its Subsidiaries or any of their property or assets may be bound or affected, (iv) require any action by, filing, registration,
or qualification with, or Governmental Approval from, any 

  
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Governmental Authority (except such Governmental Approvals which have already been obtained and are in full force and effect), or (v) constitute an event of default under any material
agreement by which Borrower is bound. Borrower is not in default under any agreement to which it is a party or by which it is bound in which the default could reasonably be expected to have a material adverse effect on Borrower’s business. 

5.2 Collateral. Borrower has good title to, has rights in, and the power to transfer, each item of the Collateral upon which it
purports to grant a Lien hereunder, free and clear of any and all Liens except Permitted Liens. Borrower has no deposit accounts other than the deposit accounts with Bank, the deposit accounts, if any, described in the Perfection Certificate
delivered to Bank in connection herewith, or of which Borrower has given Bank notice and taken such actions as are necessary to give Bank a perfected security interest therein. The Accounts are bona fide, existing obligations of the Account Debtors.
All Inventory is in all material respects of good and marketable quality, free from material defects. 
 The Collateral is not in the
possession of any third party bailee (such as a warehouse) except as otherwise provided in the Perfection Certificate or as permitted pursuant to Section 7.2. None of the components of the Collateral are currently being maintained at locations
other than as provided in the Perfection Certificate or as permitted pursuant to Section 7.2 of this Agreement. 
 Borrower is the sole
owner of the Intellectual Property which it owns or purports to own except for (a) non-exclusive licenses granted to its customers in the ordinary course of business, (b) over-the-counter software that is commercially available to the
public, and (c) Intellectual Property licensed to Borrower and noted on the Perfection Certificate. Each Patent which it owns or purports to own and which is material to Borrower’s business is valid and enforceable, and no part of the
Intellectual Property which Borrower owns or purports to own and which is material to Borrower’s business has been judged invalid or unenforceable, in whole or in part. To the best of Borrower’s knowledge, no claim has been made that any
part of the Intellectual Property violates the rights of any third party except to the extent such claim would not reasonably be expected to have a material adverse effect on Borrower’s business. Except as noted on the Perfection Certificate,
Borrower is not a party to, nor is it bound by, any Restricted License. 
 5.3 Litigation. Except as set forth on the Perfection
Certificate, there are no actions or proceedings pending or, to the knowledge of Borrower’s Responsible Officers, threatened in writing by or against Borrower or any Subsidiary in which an adverse decision could reasonably be expected to cause
a Material Adverse Change. 
 5.4 No Material Deviation in Financial Statements and Deterioration in Financial Condition. All
consolidated financial statements for Borrower and any Subsidiary delivered to Bank fairly present in all material respects Borrower’s consolidated financial condition and Borrower’s consolidated results of operations as of the date and
for the periods covered thereby. There has not been any material deterioration in Borrower’s consolidated financial condition since the date of the most recent financial statements submitted to Bank. 

5.5 Solvency. The fair salable value of Borrower’s assets (including goodwill minus disposition costs) exceeds the fair value of
its liabilities; Borrower is not left with unreasonably small capital after the transactions in this Agreement; and Borrower is able to pay its debts (including trade debts) as they mature. 

5.6 Regulatory Compliance. Borrower is not an “investment company” or a company “controlled” by an “investment
company” under the Investment Company Act of 1940, as amended. Borrower is not engaged as one of its important activities in extending credit for margin stock (under Regulations X, T and U of the Federal Reserve Board of Governors). Borrower
has complied in all material respects with the Federal Fair Labor Standards Act. Borrower has not violated any laws, ordinances or rules, the violation of which could reasonably be expected to cause a Material Adverse Change. None of Borrower’s
or any Subsidiary’s properties or assets have been used by Borrower or any Subsidiary or, to the best of Borrower’s knowledge, by previous Persons, in disposing, producing, storing, treating, or transporting any hazardous substance other
than legally. Borrower and each of its Subsidiaries have obtained all consents, approvals and authorizations of, made all declarations or filings with, and given all notices to, all Governmental Authorities that are necessary to continue their
respective businesses as currently conducted. 
 5.7 Subsidiaries. Borrower does not own any stock, membership interest, partnership
interest or other equity securities except for Permitted Investments. 

  
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 5.8 Tax Returns and Payments; Pension Contributions. Except as noted on the Perfection
Certificate, Borrower and each Subsidiary have timely filed or have obtained extensions for filing all required tax returns and reports, and Borrower and each Subsidiary have timely paid all foreign, federal, state and local taxes, assessments,
deposits and contributions owed by Borrower and each Subsidiary. Borrower may defer payment of any contested taxes, provided that Borrower (a) in good faith contests its obligation to pay the taxes by appropriate proceedings promptly and
diligently instituted and conducted, (b) notifies Bank in writing of the commencement of, and any material development in, the proceedings and (c) posts bonds or takes any other steps required to prevent the Governmental Authority levying
such contested taxes from obtaining a Lien upon any of the Collateral that is other than a “Permitted Lien”. Borrower is unaware of any claims or adjustments proposed for any of Borrowers prior tax years which could result in additional
taxes becoming due and payable by Borrower. Borrower has paid all amounts necessary to fund all present pension, profit sharing and deferred compensation plans in accordance with their terms, and Borrower has not withdrawn from participation in, and
has not permitted partial or complete termination of, or permitted the occurrence of any other event with respect to, any such plan which could reasonably be expected to result in any liability of Borrower, including any liability to the Pension
Benefit Guaranty Corporation or its successors or any other governmental agency. 
 5.9 Full Disclosure. No written representation,
warranty or other statement of Borrower in any certificate or written statement given to Bank, as of the date such representation, warranty, or other statement was made, taken together with all such written certificates and written statements given
to Bank, contains any untrue statement of a material fact or omits to state a material fact necessary to make the statements contained in the certificates or statements not misleading (it being recognized by Bank that any projections and forecasts
provided by Borrower in good faith and based upon reasonable assumptions are not viewed as facts and that actual results during the period or periods covered by such projections and forecasts may differ from the projected or forecasted results).

  

	 	6	AFFIRMATIVE COVENANTS 

 Borrower shall do all of the following: 

6.1 Government Compliance 

(a) Maintain its and all its Subsidiaries’ legal existence and good standing in their respective jurisdictions of formation and maintain
qualification in each other jurisdiction in which the failure to so qualify would reasonably be expected to have a material adverse effect on Borrower’s business or operations. Borrower shall comply, and have each Subsidiary comply, with all
laws, ordinances and regulations to which it is subject, noncompliance with which could reasonably be expected to have a material adverse effect on Borrower’s business. Notwithstanding the foregoing, nothing herein shall prohibit Borrower from
dissolving the following Subsidiaries on or prior to December 31, 2013 – Mobilisafe, Inc., Rapid7 Middle Holding, Inc. and Rapid7 Holding Company. 

(b) Obtain all of the Governmental Approvals necessary for the performance by Borrower of its obligations under the Loan Documents to which it
is a party and the grant of a security interest to Bank in all of its property. Borrower shall promptly provide copies of any such obtained Governmental Approvals to Bank. 

(c) Deliver to Bank, within five (5) days after the same are sent or received, copies of all correspondence, reports, documents and other
filings with any Governmental Authority regarding compliance with or maintenance of Governmental Approvals or Requirements of Law or that could reasonably be expected to have a material adverse effect on any of the Governmental Approvals or
otherwise on the operations of Borrower or any of its Subsidiaries. 
 6.2 Financial Statements, Reports, Certificates 

(a) Deliver to Bank: (i) as soon as available, but no later than thirty (30) days after the last day of each Reconciliation Period,
a company prepared consolidated and consolidating balance sheet and income statement covering Borrower’s and each of its Subsidiaries’ consolidated and consolidating operations during the period certified by a Responsible Officer and in a
form acceptable to Bank; (ii) as soon as available, but no later than one hundred eighty (180) days after the last day of Borrower’s fiscal year, audited consolidated and consolidating financial statements prepared under GAAP,
consistently applied, together with an unqualified opinion on the financial statements from an independent certified public accounting firm reasonably acceptable to Bank; (iii) in the 

  
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event that Borrower becomes subject to the reporting requirements under the Exchange Act, within five (5) days of filing, copies of all statements, reports and notices made available to
Borrower’s security holders or to any holders of Subordinated Debt and all reports on Form 10-K, 10-Q and 8-K filed with the SEC; (iv) a prompt report of any legal actions pending or threatened in writing against Borrower or any Subsidiary
that could result in damages or costs to Borrower or any Subsidiary of One Hundred Thousand Dollars ($100,000.00) or more; (v) as soon as available, but no later than the earlier to occur of (A) sixty (60) days after the last day of
Borrower’s fiscal year and (B) ten (10) days after approval by Borrower’s board of directors, and within fifteen (15) days of any updates or amendments thereto, annual financial projections for the then current fiscal year
approved by Borrower’s board of directors (or the limited liability company equivalent thereof) and commensurate in form and substance with those provided to Borrower’s venture capital investors, together with any related business
forecasts used in the preparation of such annual financial plans and projections and (vi) budgets, sales projections, operating plans or other financial information reasonably requested by Bank. 

(b) Within thirty (30) days after the last day of each Reconciliation Period, deliver to Bank with the monthly financial statements a
Compliance Certificate signed by a Responsible Officer in the form of Exhibit B. 
 (c) Provide Bank prompt written notice of
(i) any material change in the composition of the Intellectual Property, (ii) the registration of any Copyright, including any subsequent ownership right of Borrower in or to any Copyright, Patent or Trademark not shown in the IP
Agreement, and (iii) Borrower’s knowledge of an event that could reasonably be expected to materially and adversely affect the value of the Intellectual Property. 

6.3 Taxes. Make, and cause each Subsidiary to make, timely payment of all foreign, federal, state, and local taxes or assessments
(other than taxes and assessments which Borrower is contesting in good faith, with adequate reserves maintained in accordance with GAAP) and will deliver to Bank, on demand, appropriate certificates attesting to such payments. 

6.4 Insurance. Keep its business and the Collateral insured for risks and in amounts standard for companies in Borrower’s industry
and location, and as Bank may reasonably request. Insurance policies shall be in a form, with companies, and in amounts that are satisfactory to Bank. All property policies shall have a lender’s loss payable endorsement showing Bank as lender
loss payee and waive subrogation against Bank, and all liability policies shall show, or have endorsements showing, Bank as an additional insured. All policies (or the lender loss payable and additional insured endorsements) shall provide that the
insurer must give Bank at least twenty (20) days notice before canceling, amending, or declining to renew its policy. At Bank’s request, Borrower shall deliver certified copies of policies and evidence of all premium payments. Proceeds
payable under any policy shall, at Bank’s option, be payable to Bank on account of the Obligations. Notwithstanding the foregoing, (a) so long as no Event of Default has occurred and is continuing, Borrower shall have the option of
applying the proceeds of any casualty policy up to One Hundred Thousand Dollars ($100,000.00), individually or in the aggregate, for all losses under all casualty policies in any one year, toward the replacement or repair of destroyed or damaged
property; provided that any such replaced or repaired property (i) shall be of equal or like value as the replaced or repaired Collateral and (ii) shall be deemed Collateral in which Bank has been granted a first priority security
interest, and (b) after the occurrence and during the continuance of an Event of Default, all proceeds payable under such casualty policy shall, at the option of Bank, be payable to Bank on account of the Obligations. If Borrower fails to
obtain insurance as required under this Section 6.4 or to pay any amount or furnish any required proof of payment to third persons and Bank, Bank may make all or part of such payment or obtain such insurance policies required in this
Section 6.4, and take any action under the policies Bank deems prudent. 
 6.5 Accounts 

(a) To permit Bank to monitor Borrower’s financial performance and condition, maintain all of Borrower’s and its Subsidiaries’
depository and operating accounts and securities/investment accounts with Bank and Bank’s Affiliates provided, however, Borrower may maintain deposit accounts with financial institutions other than Bank so long as the aggregate amount of funds
held in such accounts (in the aggregate for all such accounts together) does not exceed Two Hundred Fifty Thousand Dollars ($250,000.00) as of the last day of each month (the “Permitted Accounts”). 

(b) For any Collateral Account that Bank in its sole discretion permits Borrower at any time to open or maintain, Borrower shall cause the
applicable bank or financial institution (other than Bank) at or with which any Collateral Account is maintained to execute and deliver a Control Agreement or other appropriate instrument with respect to such Collateral Account to perfect
Bank’s Lien in such Collateral Account in accordance with the terms hereunder which Control Agreement may not be terminated without the prior written consent of Bank. The provisions of the previous sentence shall not apply to (i) deposit
accounts exclusively used for payroll, payroll taxes and other employee wage and benefit payments to or for the benefit of Borrower’s employees and identified to Bank by Borrower as such or (ii) the Permitted Accounts. 

  
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 6.6 Inventory; Returns. Keep all Inventory in good and marketable condition, free from
material defects. Returns and allowances between Borrower and its Account Debtors shall follow Borrower’s customary practices as they exist at the Effective Date. If, at any time during the term of this Agreement, any there is any return,
recovery, dispute or claim that involves more than One Hundred Thousand Dollars ($100,000.00), Borrower issues a credit memorandum, or any representation, warranty or covenant set forth in this Agreement or the other Loan Documents is no longer true
in all material respects, Borrower will promptly advise Bank. 
 6.7 Protection and Registration of Intellectual Property Rights 

(a) (i) Use commercially reasonable efforts to protect, defend and maintain the validity and enforceability of its Intellectual Property,
which is material to Borrower’s business; (ii) promptly advise Bank in writing of material infringements of its Intellectual Property; and (iii) not allow any Intellectual Property material to Borrower’s business to be abandoned,
forfeited or dedicated to the public without Bank’s written consent. 
 (b) If Borrower (i) obtains any Patent, registered
Trademark, registered Copyright, registered mask work, or any pending application for any of the foregoing, whether as owner, licensee or otherwise, or (ii) applies for any Patent or the registration of any Trademark, then Borrower shall,
within fifteen (15) Business Days, provide written notice thereof to Bank and shall execute such intellectual property security agreements and other documents and take such other actions as Bank shall request in its good faith business judgment
to perfect and maintain a first priority perfected security interest in favor of Bank in such property. If Borrower decides to register any Copyrights or mask works in the United States Copyright Office, Borrower shall: (x) provide Bank with at
least fifteen (15) days prior written notice of Borrower’s intent to register such Copyrights or mask works together with a copy of the application it intends to file with the United States Copyright Office (excluding exhibits thereto);
(y) execute an intellectual property security agreement and such other documents and take such other actions as Bank may request in its good faith business judgment to perfect and maintain a first priority perfected security interest in favor
of Bank in the Copyrights or mask works intended to be registered with the United States Copyright Office; and (z) record such intellectual property security agreement with the United States Copyright Office contemporaneously with filing the
Copyright or mask work application(s) with the United States Copyright Office. Borrower shall promptly provide to Bank copies of all applications that it files for Patents or for the registration of Trademarks, Copyrights or mask works, together
with evidence of the recording of the intellectual property security agreement necessary for Bank to perfect and maintain a first priority perfected security interest in such property. 

(c) Provide written notice to Bank within thirty (30) days of entering or becoming bound by any Restricted License (other than
over-the-counter software that is commercially available to the public). Borrower shall take such steps as Bank requests to obtain the consent of, or waiver by, any person whose consent or waiver is necessary for (i) any Restricted License to
be deemed “Collateral” and for Bank to have a security interest in it that might otherwise be restricted or prohibited by law or by the terms of any such Restricted License, whether now existing or entered into in the future, and
(ii) Bank to have the ability in the event of a liquidation of any Collateral to dispose of such Collateral in accordance with Bank’s rights and remedies under this Agreement and the other Loan Documents. 

6.8 Litigation Cooperation. From the Effective Date and continuing through the termination of this Agreement, make available to Bank,
without expense to Bank, Borrower and its officers, employees and agents and Borrower’s Books, to the extent that Bank may deem them reasonably necessary to prosecute or defend any third party suit or proceeding instituted by or against Bank
with respect to any Collateral or relating to Borrower. 
 6.9 Further Assurances. Execute any further instruments and take further
action as Bank reasonably requests to perfect or continue Bank’s Lien in the Collateral or to effect the purposes of this Agreement. 

  
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	 	7	NEGATIVE COVENANTS 

 Borrower shall not do any of the following without Bank’s prior
written consent: 
 7.1 Dispositions. Convey, sell, lease, transfer, assign, or otherwise dispose of (collectively a
“Transfer”), or permit any of its Subsidiaries to Transfer, all or any part of its business or property, except for Transfers (a) of Inventory in the ordinary course of business; (b) of worn-out or obsolete Equipment;
(c) in connection with Permitted Liens and Permitted Investments; (d) of non-exclusive licenses for the use of the property of Borrower or its Subsidiaries in the ordinary course of business; and (e) of Intellectual Property to Rapid7
UK so long as, contemporaneously with any such Transfer, Rapid7 UK has become a guarantor or co-borrower hereunder (as determined by Bank) pursuant to documentation acceptable to Bank and Bank has a first priority perfected security interest in all
assets of Rapid7 UK (which shall include, without limitation, the Intellectual Property that is transferred immediately after giving effect to such Transfer) under any laws applicable to such assets, subject only to Permitted Liens that are
permitted to have priority over Bank’s Liens hereunder. 
 7.2 Changes in Business, Management, Ownership, or Business
Locations. (a) Engage in or permit any of its Subsidiaries to engage in any business other than the businesses currently engaged in by Borrower and such Subsidiary, as applicable, or reasonably related thereto; (b) liquidate or
dissolve; or (c) (i) have a change in management such that the Chief Executive Officer or the Chief Financial Officer ceases to hold such office with Borrower and a replacement satisfactory to Borrower’s board of directors is not made
within ninety (90) days after such Chief Executive Officer’s or such Chief Financial Officer’s departure from Borrower; or (ii) enter into any transaction or series of related transactions in which the stockholders or members of
Borrower who were not stockholders or members immediately prior to the first such transaction own more than forty percent (40.0%) of the voting stock or membership interests of Borrower immediately after giving effect to such transaction or
related series of such transactions (other than by the sale of Borrower’s equity securities in a public offering or to venture capital investors so long as Borrower identifies to Bank the venture capital investors prior to the closing of the
transaction and provides to Bank a description of the material terms of the transaction). 
 Borrower shall not, without at least thirty
(30) days prior written notice to Bank: (1) add any new offices or business locations, including warehouses (unless such new offices or business locations contain less than Twenty Thousand Dollars ($20,000.00) in Borrower’s assets or
property), (2) change its jurisdiction of organization, (3) change its organizational structure or type, (4) change its legal name, (5) change any organizational number (if any) assigned by its jurisdiction of organization, or
(6) deliver any portion of the Collateral to a bailee, unless (i) such bailee location contains less than Twenty Thousand Dollars ($20,000.00) in Borrower’s assets or property and (ii) Bank and such bailee are parties to a bailee
agreement governing both the Collateral and the location to which Borrower intends to deliver the Collateral. 
 Borrower hereby agrees upon
Borrower adding any new office or business location, including any warehouse, Borrower will cause its landlord to enter into a landlord consent in favor of Bank prior to such new office or business location containing Twenty Thousand Dollars
($20,000.00) of Collateral. 
 Borrower hereby agrees that prior to Borrower delivering any Collateral (with an aggregate value of more than
Twenty Thousand Dollars ($20,000.00) to a bailee, Borrower shall cause such bailee to execute and deliver a bailee agreement in form and substance satisfactory to Bank. 

7.3 Mergers or Acquisitions. Merge or consolidate, or permit any of its Subsidiaries to merge or consolidate, with any other Person, or
acquire, or permit any of its Subsidiaries to acquire, all or substantially all of the capital stock, membership interests, or property of another Person. A Subsidiary may merge or consolidate into another Subsidiary or into Borrower. 

7.4 Indebtedness. Create, incur, assume, or be liable for any Indebtedness, or permit any Subsidiary to do so, other than Permitted
Indebtedness. 
 7.5 Encumbrance. Create, incur, allow, or suffer any Lien on any of its property, or assign or convey any right to
receive income, including the sale of any Accounts, or permit any of its Subsidiaries to do so, except for Permitted Liens, or permit any Collateral not to be subject to the first priority security interest granted herein (subject to Permitted Liens
that are permitted to have priority over Bank’s Liens hereunder), or enter into any 

  
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agreement, document, instrument or other arrangement (except with or in favor of Bank) with any Person which directly or indirectly prohibits or has the effect of prohibiting Borrower or any
Subsidiary from assigning, mortgaging, pledging, granting a security interest in or upon, or encumbering any of Borrower’s or any Subsidiary’s Intellectual Property, except as is otherwise permitted in Section 7.1 of this Agreement
and the definition of “Permitted Liens” herein. 
 7.6 Maintenance of Collateral Accounts. Maintain any Collateral Account
except pursuant to the terms of Section 6.5 of this Agreement. 
 7.7 Distributions; Investments. (a) Directly or
indirectly acquire or own any Person, or make any Investment in any Person, other than Permitted Investments, or permit any of its Subsidiaries to do so; or (b) pay any dividends or make any distribution or payment or redeem, retire or purchase
any capital stock or membership interests; provided that, Borrower may repurchase the stock of former employees or consultants pursuant to stock repurchase agreements so long as an Event of Default does not exist at the time of such repurchase and
would not exist after giving effect to such repurchase, and provided further that such repurchases do not exceed in the aggregate Fifty Thousand Dollars ($50,000) per fiscal year. 

7.8 Transactions with Affiliates. Directly or indirectly enter into or permit to exist any material transaction with any Affiliate of
Borrower, except for (i) transactions that are in the ordinary course of Borrower’s business, upon fair and reasonable terms that are no less favorable to Borrower than would be obtained in an arm’s length transaction with a
non-affiliated Person, (ii) equity financings that are permitted pursuant to the terms of Section 7.2 hereof, (iii) transactions described in and permitted pursuant to the terms of the second sentence of Section 7.3 hereof,
(iv) Investments permitted under sub-clause (1) of the definition of Permitted Investments, and (v) Indebtedness financings with Borrower’s investors so long as all such Indebtedness is Subordinated Debt. 

7.9 Subordinated Debt. (a) Make or permit any payment on any Subordinated Debt, except under the terms of the subordination,
intercreditor, or other similar agreement to which such Subordinated Debt is subject, or (b) amend any provision in any document relating to the Subordinated Debt which would increase the amount owed by Borrower thereof, shorten the maturity
thereof, increase the rate of interest applicable thereto or adversely affect the subordination thereof to Obligations owed to Bank. 

7.10 Compliance. Become an “investment company” or a company controlled by an “investment company”, under the
Investment Company Act of 1940, as amended, or undertake as one of its important activities extending credit to purchase or carry margin stock (as defined in Regulation U of the Board of Governors of the Federal Reserve System), or use the proceeds
of any Credit Extension for that purpose; fail to meet the minimum funding requirements of ERISA, permit a Reportable Event or Prohibited Transaction, each as defined in ERISA, to occur; fail to comply with the Federal Fair Labor Standards Act or
violate any other law or regulation, if the violation could reasonably be expected to have a material adverse effect on Borrower’s business, or permit any of its Subsidiaries to do so; withdraw or permit any Subsidiary to withdraw from
participation in, permit partial or complete termination of, or permit the occurrence of any other event with respect to, any present pension, profit sharing and deferred compensation plan which could reasonably be expected to result in any
liability of Borrower, including any liability to the Pension Benefit Guaranty Corporation or its successors or any other governmental agency. 
  

	 	8	EVENTS OF DEFAULT 

 Any one of the following shall constitute an event of default (an
“Event of Default”) under this Agreement: 
 8.1 Payment Default. Borrower fails to (a) make any payment of
principal or interest on any Credit Extension when due, or (b) pay any other Obligations within three (3) Business Days after such Obligations are due and payable (which three (3) Business Day cure period shall not apply to payments
due on the Maturity Date). During the cure period, the failure to make or pay any payment specified under clause (b) hereunder is not an Event of Default (but no Credit Extension will be made during the cure period); 

8.2 Covenant Default. Borrower fails or neglects to perform any obligation in Section 6 of this Agreement or violates any covenant
in Section 7 of this Agreement or fails or neglects to perform, keep, or observe 

  
 11 

 
any other term, provision, condition, covenant or agreement contained in this Agreement, any Loan Documents and as to any default under such other term, provision, condition, covenant or
agreement that can be cured, has failed to cure the default within ten (10) days after the occurrence thereof; provided, however, grace and cure periods provided under this Section 8.2 shall not apply to financial covenants or any other
covenants that are required to be satisfied, completed or tested by a date certain; 
 8.3 Material Adverse Change. A Material
Adverse Change occurs; 
 8.4 Attachment; Levy; Restraint on Business 

(a) (i) The service of process seeking to attach, by trustee or similar process, any funds of Borrower or of any entity under the control
of Borrower (including a Subsidiary) on deposit or otherwise maintained with Bank or any Bank Affiliate, or (ii) a notice of lien or levy is filed against any of Borrower’s assets by any government agency, and the same under subclauses
(i) and (ii) hereof are not, within ten (10) days after the occurrence thereof, discharged or stayed (whether through the posting of a bond or otherwise); provided, however, no Credit Extensions shall be made during any ten
(10) day cure period; or 
 (b) (i) any material portion of Borrower’s assets is attached, seized, levied on, or comes into
possession of a trustee or receiver, or (ii) any court order enjoins, restrains, or prevents Borrower from conducting any material part of its business; 

8.5 Insolvency. (a) Borrower is unable to pay its debts (including trade debts) as they become due or otherwise becomes insolvent;
(b) Borrower begins an Insolvency Proceeding; or (c) an Insolvency Proceeding is begun against Borrower and not dismissed or stayed within thirty (30) days (but no Credit Extensions shall be made while of any of the conditions
described in clause (a) exist and/or until any Insolvency Proceeding is dismissed); 
 8.6 Other Agreements. There is, under any
agreement to which Borrower is a party with a third party or parties, (a) any default resulting in a right by such third party or parties, whether or not exercised, to accelerate the maturity of any Indebtedness in an amount individually or in
the aggregate in excess of One Hundred Thousand Dollars ($100,000.00); or (b) any default by Borrower, the result of which could result in a Material Adverse Change to Borrower’s business; provided, however, that the Event of
Default under this Section 8.6 caused by the occurrence of a default under such other agreement shall be cured or waived for purposes of this Agreement upon Bank receiving written notice from the party asserting such default of such cure or
waiver of the default under such other agreement, if at the time of such cure or waiver under such other agreement (x) Bank has not declared an Event of Default under this Agreement and/or exercised any rights with respect thereto; (y) any
such cure or waiver does not result in an Event of Default under any other provision of this Agreement or any Loan Document; and (z) in connection with any such cure or waiver under such other agreement, the terms of any agreement with such
third party are not modified or amended in any manner which could in the good faith judgment of Bank be materially more burdensome to Borrower; 

8.7 Judgments. One or more final judgments, orders, or decrees for the payment of money in an amount, individually or in the aggregate,
of at least One Hundred Thousand Dollars ($100,000.00) (not covered by independent third-party insurance as to which liability has been accepted by such insurance carrier) shall be rendered against Borrower and the same are not, within ten
(10) days after the entry thereof, discharged or execution thereof stayed or bonded pending appeal, or such judgments are not discharged prior to the expiration of any such stay (provided that no Credit Extensions will be made prior to the
discharge, stay, or bonding of such judgment, order, or decree); 
 8.8 Misrepresentations. Borrower or any Person acting for
Borrower makes any representation, warranty, or other statement now or later in this Agreement, any Loan Document or in any writing delivered to Bank or to induce Bank to enter this Agreement or any Loan Document, and such representation, warranty,
or other statement is incorrect in any material respect when made; 
 8.9 Subordinated Debt. Any document, instrument, or agreement
evidencing the subordination of any Subordinated Debt shall for any reason be revoked or invalidated or otherwise cease to be in full force and effect, any Person shall be in breach thereof or contest in any manner the validity or enforceability
thereof or deny that it has any further liability or obligation thereunder, or the Obligations shall for any reason be subordinated or shall not have the priority contemplated by this Agreement or the applicable subordination agreement; 

  
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 8.10 Governmental Approvals. Any Governmental Approval shall have been (a) revoked,
rescinded, suspended, modified in an adverse manner or not renewed in the ordinary course for a full term or (b) subject to any decision by a Governmental Authority that designates a hearing with respect to any applications for renewal of any
such Governmental Approval or that could result in the Governmental Authority taking any of the actions described in clause (a) above, and such decision or such revocation, rescission, suspension, modification or non-renewal (i) has, or
could reasonably be expected to have, a Material Adverse Change, or (ii) adversely affects the legal qualifications of Borrower or any of its Subsidiaries to hold such Governmental Approval in any applicable jurisdiction and such revocation,
rescission, suspension, modification or non-renewal could reasonably be expected to affect the status of or legal qualifications of Borrower or any of its Subsidiaries to hold any Governmental Approval in any other jurisdiction; or 

8.11 Senior Loan Agreement. The occurrence of an Event of Default (as defined in the Senior Loan Agreement) under the Senior Loan
Agreement, other than an Event of Default solely resulting from Borrower’s failure to comply with Section 6.10 of the Senior Loan Agreement. 
  

	 	9	BANK’S RIGHTS AND REMEDIES 

 9.1 Rights and Remedies. When an Event of
Default occurs and continues beyond any applicable grace period Bank may, without notice or demand, do any or all of the following: 
 (a)
declare all Obligations immediately due and payable (but if an Event of Default described in Section 8.5 of this Agreement occurs, all Obligations are immediately due and payable without any action by Bank); 

(b) stop advancing money or extending credit for Borrower’s benefit under this Agreement or under any other agreement between Borrower
and Bank; 
 (c) demand that Borrower (i) deposit cash with Bank in an amount equal to one hundred five percent (105.0%) for
Letters of Credit denominated in Dollars and one hundred ten percent (110.0%) for Letters of Credit denominated in a currency other than Dollars, in each case of the Dollar Equivalent of the aggregate face amount of all Letters of Credit
remaining undrawn (plus all interest, fees, and costs due or to become due in connection therewith (as estimated by Bank in its good faith business judgment)), to secure all of the Obligations relating to such Letters of Credit, as collateral
security for the repayment of any future drawings under such Letters of Credit, and Borrower shall forthwith deposit and pay such amounts, and (ii) pay in advance all letter of credit fees scheduled to be paid or payable over the remaining term
of any Letters of Credit; 
 (d) settle or adjust disputes and claims directly with Account Debtors for amounts, on terms and in any order
that Bank considers advisable and notify any Person owing Borrower money of Bank’s security interest in such funds and verify the amount of such account. Borrower shall collect all payments in trust for Bank and, if requested by Bank,
immediately deliver the payments to Bank in the form received from the Account Debtor, with proper endorsements for deposit; 
 (e) make any
payments and do any acts it considers necessary or reasonable to protect its security interest in the Collateral. Borrower shall assemble the Collateral if Bank requests and make it available as Bank designates. Bank may enter premises where the
Collateral is located, take and maintain possession of any part of the Collateral, and pay, purchase, contest, or compromise any Lien which appears to be prior or superior to its security interest and pay all expenses incurred. Borrower grants Bank
a license to enter and occupy any of its premises, without charge, to exercise any of Bank’s rights or remedies; 
 (f) apply to the
Obligations any (i) balances and deposits of Borrower it holds, or (ii) amount held by Bank owing to or for the credit or the account of Borrower; 

(g) ship, reclaim, recover, store, finish, maintain, repair, prepare for sale, advertise for sale, and sell the Collateral. Bank is hereby
granted a non-exclusive, royalty-free license or other right to use, without 

  
 13 

 
charge, Borrower’s labels, Patents, Copyrights, mask works, rights of use of any name, trade secrets, trade names, Trademarks, and advertising matter, or any similar property as it pertains
to the Collateral, in completing production of, advertising for sale, and selling any Collateral and, in connection with Bank’s exercise of its rights under this Section 9.1, Borrower’s rights under all licenses and all franchise
agreements inure to Bank’s benefit; 
 (h) place a “hold” on any account maintained with Bank and/or deliver a notice of
exclusive control, any entitlement order, or other directions or instructions pursuant to any Control Agreement or similar agreements providing control of any Collateral; 

(i) demand and receive possession of Borrower’s Books; and 

(j) exercise all rights and remedies available to Bank under the Loan Documents or at law or equity, including all remedies provided under the
Code (including disposal of the Collateral pursuant to the terms thereof). 
 9.2 Power of Attorney. Borrower hereby irrevocably
appoints Bank as its lawful attorney-in-fact, exercisable upon the occurrence and during the continuance of an Event of Default, to: (a) endorse Borrower’s name on any checks or other forms of payment or security; (b) sign
Borrower’s name on any invoice or bill of lading for any Account or drafts against Account Debtors; (c) settle and adjust disputes and claims about the Accounts directly with Account Debtors, for amounts and on terms Bank determines
reasonable; (d) make, settle, and adjust all claims under Borrower’s insurance policies; (e) pay, contest or settle any Lien, charge, encumbrance, security interest, and adverse claim in or to the Collateral, or any judgment based
thereon, or otherwise take any action to terminate or discharge the same; and (f) transfer the Collateral into the name of Bank or a third party as the Code permits. Borrower hereby appoints Bank as its lawful attorney-in-fact to sign
Borrower’s name on any documents necessary to perfect or continue the perfection of Bank’s security interest in the Collateral regardless of whether an Event of Default has occurred until all Obligations (other than inchoate indemnity
obligations) have been repaid in full in cash and Bank is under no further obligation to make Credit Extensions hereunder. Bank’s foregoing appointment as Borrower’s attorney in fact, and all of Bank’s rights and powers, coupled with
an interest, are irrevocable until all Obligations (other than inchoate indemnity obligations) have been fully repaid and satisfied and Bank’s obligation to provide Credit Extensions terminates. 

9.3 Protective Payments. If Borrower fails to obtain the insurance called for by Section 6.4 of this Agreement or fails to pay any
premium thereon or fails to pay any other amount which Borrower is obligated to pay under this Agreement or any other Loan Document, Bank may obtain such insurance or make such payment, and all amounts so paid by Bank are Bank Expenses and
immediately due and payable, bearing interest at the then highest rate applicable to the Obligations, and secured by the Collateral. Bank will make reasonable efforts to provide Borrower with notice of Bank obtaining such insurance at the time it is
obtained or within a reasonable time thereafter. No payments by Bank are deemed an agreement to make similar payments in the future or Bank’s waiver of any Event of Default. 

9.4 Application of Payments and Proceeds Upon Default. If an Event of Default has occurred and is continuing, Bank shall have the right
to apply in any order any funds in its possession, whether from Borrower account balances, payments, proceeds realized as the result of any collection of Accounts or other disposition of the Collateral, or otherwise, to the Obligations. Bank shall
pay any surplus to Borrower by credit to the Designated Deposit Account or to other Persons legally entitled thereto; Borrower shall remain liable to Bank for any deficiency. If Bank, directly or indirectly, enters into a deferred payment or other
credit transaction with any purchaser at any sale of Collateral, Bank shall have the option, exercisable at any time, of either reducing the Obligations by the principal amount of the purchase price or deferring the reduction of the Obligations
until the actual receipt by Bank of cash therefor. 
 9.5 Bank’s Liability for Collateral. So long as Bank complies with
reasonable banking practices regarding the safekeeping of the Collateral in the possession or under the control of Bank, Bank shall not be liable or responsible for: (a) the safekeeping of the Collateral; (b) any loss or damage to the
Collateral; (c) any diminution in the value of the Collateral; or (d) any act or default of any carrier, warehouseman, bailee, or other Person. Borrower bears all risk of loss, damage or destruction of the Collateral. 

  
 14 

 9.6 No Waiver; Remedies Cumulative. Bank’s failure, at any time or times, to require
strict performance by Borrower of any provision of this Agreement or any other Loan Document shall not waive, affect, or diminish any right of Bank thereafter to demand strict performance and compliance herewith or therewith. No waiver hereunder
shall be effective unless signed by the party granting the waiver and then is only effective for the specific instance and purpose for which it is given. Bank’s rights and remedies under this Agreement and the other Loan Documents are
cumulative. Bank has all rights and remedies provided under the Code, by law, or in equity. Bank’s exercise of one right or remedy is not an election and shall not preclude Bank from exercising any other remedy under this Agreement or other
remedy available at law or in equity, and Bank’s waiver of any Event of Default is not a continuing waiver. Bank’s delay in exercising any remedy is not a waiver, election, or acquiescence. 

9.7 Demand Waiver. Borrower waives demand, notice of default or dishonor, notice of payment and nonpayment, notice of any default,
nonpayment at maturity, release, compromise, settlement, extension, or renewal of accounts, documents, instruments, chattel paper, and guarantees held by Bank on which Borrower is liable. 

9.8 Borrower Liability. Either Borrower may, acting singly, request Credit Extensions hereunder. Each Borrower hereby appoints the
other as agent for itself for all purposes hereunder, including with respect to requesting Credit Extensions hereunder. Each Borrower hereunder shall be jointly and severally obligated to repay all Credit Extensions made hereunder, regardless of
which Borrower actually receives said Credit Extensions, as if each Borrower hereunder directly received all Credit Extensions. Each Borrower waives (a) any suretyship defenses available to it under the Code or any other applicable law, and
(b) any right to require Bank to: (i) proceed against any Borrower or any other person; (ii) proceed against or exhaust any security; or (iii) pursue any other remedy. Bank may exercise or not exercise any right or remedy it has
against any Borrower or any security it holds (including the right to foreclose by judicial or non-judicial sale) without affecting any Borrower’s liability. 

Notwithstanding any other provision of this Agreement or other related document, each Borrower irrevocably waives all rights that it may have
at law or in equity (including, without limitation, any law subrogating Borrower to the rights of Bank under this Agreement) to seek contribution, indemnification or any other form of reimbursement from any other Borrower, or any other Person now or
hereafter primarily or secondarily liable for any of the Obligations, for any payment made by Borrower with respect to the Obligations in connection with this Agreement or otherwise and all rights that it might have to benefit from, or to
participate in, any security for the Obligations as a result of any payment made by Borrower with respect to the Obligations in connection with this Agreement or otherwise. Any agreement providing for indemnification, reimbursement or any other
arrangement prohibited under this Section 9.8 shall be null and void. If any payment is made to a Borrower in contravention of this Section 9.8, such Borrower shall hold such payment in trust for Bank and such payment shall be promptly
delivered to Bank for application to the Obligations, whether matured or unmatured. 
  

	 	10	NOTICES 

 All notices, consents, requests, approvals, demands, or other communication by
any party to this Agreement or any other Loan Document must be in writing and shall be deemed to have been validly served, given, or delivered: (a) upon the earlier of actual receipt and three (3) Business Days after deposit in the U.S.
mail, first class, registered or certified mail return receipt requested, with proper postage prepaid; (b) upon transmission, when sent by electronic mail or facsimile transmission; (c) one (1) Business Day after deposit with a
reputable overnight courier with all charges prepaid; or (d) when delivered, if hand-delivered by messenger, all of which shall be addressed to the party to be notified and sent to the address, facsimile number, or email address indicated
below. Bank or Borrower may change its mailing or electronic mail address or facsimile number by giving the other party written notice thereof in accordance with the terms of this Section 10. 

 

					
	If to Borrower:		RAPID7, INC. and RAPID7 LLC
			800 Boylston Street
			Prudential Tower, 29th Floor
			Boston, MA 02199
			Attn:		Steven Gatoff, CFO
			Fax:		(617) 830-8251
			Email:		SGatoff@rapid7.com

  
 15 

					
	If to Bank:		Silicon Valley Bank
			275 Grove Street
			Suite 2-200
			Newton, Massachusetts 02466
			Attn:		Ms. Kate Leland
			Fax:		(617) 527-0177
			Email:		KLeland@svb.com
		
	with a copy to:		Silicon Valley Bank
			901 Fifth Avenue, Suite 3900
			Seattle, Washington 98614
			Attn: Mr. Jim Ellison
			Fax: (206) 624-0374
			E-mail: jellison@svb.com
		
	with a copy to:		Riemer & Braunstein LLP
			Three Center Plaza
			Boston, Massachusetts 02108
			Attn:		David A. Ephraim, Esquire
			Fax:		(617) 880-3456
			Email:		DEphraim@riemerlaw.com

  

	 	11	CHOICE OF LAW, VENUE AND JURY TRIAL WAIVER 

 Massachusetts law governs the Loan Documents
without regard to principles of conflicts of law. Borrower and Bank each submit to the exclusive jurisdiction of the State and Federal courts in Massachusetts; provided, however, that nothing in this Agreement shall be deemed to operate to preclude
Bank from bringing suit or taking other legal action in any other jurisdiction to realize on the Collateral or any other security for the Obligations, or to enforce a judgment or other court order in favor of Bank. Borrower expressly submits and
consents in advance to such jurisdiction in any action or suit commenced in any such court, and Borrower hereby waives any objection that it may have based upon lack of personal jurisdiction, improper venue, or forum non conveniens and hereby
consents to the granting of such legal or equitable relief as is deemed appropriate by such court. Borrower hereby waives personal service of the summons, complaints, and other process issued in such action or suit and agrees that service of such
summons, complaints, and other process may be made by registered or certified mail addressed to Borrower at the address set forth in, or subsequently provided to Borrower in accordance with, Section 10 of this Agreement and that service so made
shall be deemed completed upon the earlier to occur of Borrower’s actual receipt thereof or three (3) days after deposit in the U.S. mails, proper postage prepaid. 

BORROWER AND BANK EACH WAIVE THEIR RIGHT TO A JURY TRIAL OF ANY CLAIM OR CAUSE OF ACTION ARISING OUT OF OR BASED UPON THIS AGREEMENT, THE
LOAN DOCUMENTS OR ANY CONTEMPLATED TRANSACTION, INCLUDING CONTRACT, TORT, BREACH OF DUTY AND ALL OTHER CLAIMS. THIS WAIVER IS A MATERIAL INDUCEMENT FOR BOTH PARTIES TO ENTER INTO THIS AGREEMENT. EACH PARTY HAS REVIEWED THIS WAIVER WITH ITS COUNSEL.

  

	 	12	GENERAL PROVISIONS 

 12.1 Successors and Assigns. This Agreement binds and is for
the benefit of the successors and permitted assigns of each party. Borrower may not assign this Agreement or any rights or obligations under it without Bank’s prior written consent (which may be granted or withheld in Bank’s discretion).
Bank has the right, without the consent of or notice to Borrower, to sell, transfer, assign, negotiate, or grant participation in all or any part of, or any interest in, Bank’s obligations, rights, and benefits under this Agreement and the
other Loan Documents (other than the Warrant, as to which assignment, transfer and other such actions are governed by the terms of the Warrant). In addition and without limiting the foregoing, in consultation with Borrower, Bank may elect to
participate all or a portion of its interest under this Agreement to any Person, at no cost to Borrower, provided, however, that if such Person is not a banking institution or financial institution or other lender in the

  
 16 

 
primary business of making loans, Borrower must consent to such Person, which consent shall not be unreasonably withheld or delayed (it being acknowledged by Borrower that Borrower’s consent
is not required for a participation by WestRiver Mezzanine Loans, LLC, and that Bank has consulted with Borrower in connection with a participation by WestRiver Mezzanine Loans, LLC). 

12.2 Indemnification. Borrower agrees to indemnify, defend and hold Bank and its directors, officers, employees, agents, attorneys, or
any other Person affiliated with or representing Bank (each, an “Indemnified Person”) harmless against: (a) all obligations, demands, claims, and liabilities (collectively, “Claims”) claimed or asserted by any
other party in connection with the transactions contemplated by the Loan Documents; and (b) all losses or expenses (including Bank Expenses) in any way suffered, incurred, or paid by such Indemnified Person as a result of, following from,
consequential to, or arising from transactions between Bank and Borrower (including reasonable attorneys’ fees and expenses), except as to (a) or (b) for Claims, losses and/or Bank Expenses directly caused by such Indemnified
Person’s gross negligence or willful misconduct. 
 12.3 Right of Set-Off. Borrower hereby grants to Bank, a lien, security
interest and right of setoff as security for all Obligations to Bank, whether now existing or hereafter arising upon and against all deposits, credits, collateral and property, now or hereafter in the possession, custody, safekeeping or control of
Bank or any entity under the control of Bank (including a Bank subsidiary) or in transit to any of them. At any time after the occurrence and during the continuance of an Event of Default, without demand or notice, Bank may set off the same or any
part thereof and apply the same to any liability or obligation of Borrower even though unmatured and regardless of the adequacy of any other collateral securing the Obligations. ANY AND ALL RIGHTS TO REQUIRE BANK TO EXERCISE ITS RIGHTS OR REMEDIES
WITH RESPECT TO ANY OTHER COLLATERAL WHICH SECURES THE OBLIGATIONS, PRIOR TO EXERCISING ITS RIGHT OF SETOFF WITH RESPECT TO SUCH DEPOSITS, CREDITS OR OTHER PROPERTY OF BORROWER, ARE HEREBY KNOWINGLY, VOLUNTARILY AND IRREVOCABLY WAIVED. 

12.4 Time of Essence. Time is of the essence for the performance of all Obligations in this Agreement. 

12.5 Correction of Loan Documents. Bank may correct patent errors and fill in any blanks in the Loan Documents consistent with the
agreement of the parties so long as Bank provides Borrower with written notice of such correction and allows Borrower at least ten (10) days to object to such correction. In the event of such objection, such correction shall not be made except
by an amendment signed by both Bank and Borrower. 
 12.6 Severability of Provisions. Each provision of this Agreement is severable
from every other provision in determining the enforceability of any provision. 
 12.7 Amendments in Writing; Waiver; Integration. No
purported amendment or modification of any Loan Document, or waiver, discharge or termination of any obligation under any Loan Document, shall be enforceable or admissible unless, and only to the extent, expressly set forth in a writing signed by
the party against which enforcement or admission is sought. Without limiting the generality of the foregoing, no oral promise or statement, nor any action, inaction, delay, failure to require performance or course of conduct shall operate as, or
evidence, an amendment, supplement or waiver or have any other effect on any Loan Document. Any waiver granted shall be limited to the specific circumstance expressly described in it, and shall not apply to any subsequent or other circumstance,
whether similar or dissimilar, or give rise to, or evidence, any obligation or commitment to grant any further waiver. The Loan Documents represent the entire agreement about this subject matter and supersede prior negotiations or agreements. All
prior agreements, understandings, representations, warranties, and negotiations between the parties about the subject matter of the Loan Documents merge into the Loan Documents. 

12.8 Counterparts. This Agreement may be executed in any number of counterparts and by different parties on separate counterparts, each
of which, when executed and delivered, is an original, and all taken together, constitute one Agreement. 
 12.9 Survival. All
covenants, representations and warranties made in this Agreement continue in full force until this Agreement has terminated pursuant to its terms and all Obligations (other than inchoate indemnity obligations and any other obligations which, by
their terms, are to survive the termination of this Agreement) have been paid in full and satisfied. Without limiting the foregoing, except as otherwise provided in Section 4.1, the grant 

  
 17 

 
of a security interest by Borrower in Section 4.1 shall survive until the termination of this Agreement and all Bank Services Agreements. The obligation of Borrower in Section 12.2 of
this Agreement to indemnify Bank shall survive until the statute of limitations with respect to such claim or cause of action shall have run. 

12.10 Confidentiality. In handling any confidential information, Bank shall exercise the same degree of care that it exercises for its
own proprietary information, but disclosure of information may be made: (a) to Bank’s Subsidiaries or Affiliates (such Subsidiaries and Affiliates, together with Bank, each a “Bank Entity” and collectively, the
“Bank Entities”); (b) to prospective transferees or purchasers of any interest in the Credit Extensions (provided, however, Bank shall use its best efforts to obtain any prospective transferee’s or purchaser’s
agreement to the terms of this Section 12.10); (c) as required by law, regulation, subpoena, or other order; (d) to Bank’s regulators or as otherwise required in connection with Bank’s examination or audit; (e) as Bank
considers appropriate in exercising remedies under the Loan Documents; and (f) to third-party service providers of Bank so long as such service providers have executed a confidentiality agreement with Bank with terms no less restrictive than
those contained herein. Confidential information does not include information that is: (i) either in the public domain other than as a result of Bank’s breach of this Section 12.10 or is in Bank’s possession when disclosed to
Bank; or (ii) disclosed to Bank by a third party on a nonconfidential basis if Bank does not know that the third party is prohibited from disclosing the information. 

Bank Entities may use the confidential information for reporting purposes and the development and distribution of databases and market
analyses so long as such confidential information is aggregated and anonymized prior to distribution unless otherwise expressly prohibited by Borrower. The provisions of the immediately preceding sentence shall survive the termination of this
Agreement. 
 12.11 Electronic Execution of Documents. The words “execution,” “signed,” “signature” and
words of like import in any Loan Document shall be deemed to include electronic signatures or the keeping of records in electronic form, each of which shall be of the same legal effect, validity and enforceability as a manually executed signature or
the use of a paper-based recordkeeping systems, as the case may be, to the extent and as provided for in any applicable law, including, without limitation, any state law based on the Uniform Electronic Transactions Act. 

12.12 Captions. The headings used in this Agreement are for convenience only and shall not affect the interpretation of this Agreement.

 12.13 Construction of Agreement. The parties mutually acknowledge that they and their attorneys have participated in the
preparation and negotiation of this Agreement. In cases of uncertainty this Agreement shall be construed without regard to which of the parties caused the uncertainty to exist. 

12.14 Relationship. The relationship of the parties to this Agreement is determined solely by the provisions of this Agreement. The
parties do not intend to create any agency, partnership, joint venture, trust, fiduciary or other relationship with duties or incidents different from those of parties to an arm’s-length contract. 

12.15 Third Parties. Nothing in this Agreement, whether express or implied, is intended to: (a) confer any benefits, rights or
remedies under or by reason of this Agreement on any persons other than the express parties to it and their respective permitted successors and assigns; (b) relieve or discharge the obligation or liability of any person not an express party to
this Agreement; or (c) give any person not an express party to this Agreement any right of subrogation or action against any party to this Agreement. 
  

	 	13	DEFINITIONS 

 13.1 Definitions. As used in the Loan Documents, the word
“shall” is mandatory, the word “may” is permissive, the word “or” is not exclusive, the words “includes” and “including” are not limiting, the singular includes the plural, and numbers denoting
amounts that are set off in brackets are negative. As used in this Agreement, the following capitalized terms have the following meanings: 

“Account” is any “account” as defined in the Code with such additions to such term as may hereafter be made, and
includes, without limitation, all accounts receivable and other sums owing to Borrower. 

  
 18 

 “Account Debtor” is any “account debtor” as defined in the Code with
such additions to such term as may hereafter be made. 
 “Affiliate” of any Person is a Person that owns or controls
directly or indirectly the Person, any Person that controls or is controlled by or is under common control with the Person, and each of that Person’s senior executive officers, directors, partners, and, for any Person that is a limited
liability company, that Person’s managers and members. 
 “Agreement” is defined in the preamble of this Agreement.

 “Bank” is defined in the preamble of this Agreement. 

“Bank Entities” is defined in Section 12.10. 

“Bank Expenses” are all audit fees and expenses, costs, and expenses (including reasonable attorneys’ fees and expenses)
for preparing, amending, negotiating, administering, defending and enforcing the Loan Documents (including, without limitation, those incurred in connection with appeals or Insolvency Proceedings) or otherwise incurred with respect to Borrower. 

“Bank Services” are any products, credit services, and/or financial accommodations previously, now, or hereafter provided to
Borrower or any of its Subsidiaries by Bank or any Bank Affiliate, including, without limitation, any letters of credit, cash management services (including, without limitation, merchant services, direct deposit of payroll, business credit cards,
and check cashing services), interest rate swap arrangements, and foreign exchange services as any such products or services may be identified in Bank’s various agreements related thereto (each, a “Bank Services Agreement”).

 “Bank Services Agreement” is defined in the definition of Bank Services. 

“Borrower” is defined in the preamble of this Agreement. 

“Borrower’s Books” are all Borrower’s books and records including ledgers, federal and state tax returns, records
regarding Borrower’s assets or liabilities, the Collateral, business operations or financial condition, and all computer programs or storage or any equipment containing such information. 

“Borrowing Resolutions” are, with respect to any Person, those resolutions adopted by such Person’s board of directors
(or the limited liability company equivalent) and, if required under the terms of such Person’s Operating Documents, stockholders, members or managers, and delivered by such Person to Bank approving the Loan Documents to which such Person is a
party and the transactions contemplated thereby, together with a certificate executed by its secretary on behalf of such Person certifying that (a) such Person has the authority to execute, deliver, and perform its obligations under each of the
Loan Documents to which it is a party, (b) that attached as Exhibit A to such certificate is a true, correct, and complete copy of the resolutions then in full force and effect authorizing and ratifying the execution, delivery, and performance
by such Person of the Loan Documents to which it is a party, (c) the name(s) of the Person(s) authorized to execute the Loan Documents on behalf of such Person, together with a sample of the true signature(s) of such Person(s), and
(d) that Bank may conclusively rely on such certificate unless and until such Person shall have delivered to Bank a further certificate canceling or amending such prior certificate. 

“Business Day” is any day that is not a Saturday, Sunday or a day on which Bank is closed. 

“Cash Equivalents” means (a) marketable direct obligations issued or unconditionally guaranteed by the United States or
any agency or any State thereof having maturities of not more than one (1) year from the date of acquisition; (b) commercial paper maturing no more than one (1) year after its creation and having the highest rating from either
Standard & Poor’s Ratings Group or Moody’s Investors Service, Inc.; (c) Bank’s certificates of deposit issued maturing no more than one (1) year after issue; and (d) money market funds at least ninety-five
percent (95%) of the assets of which constitute Cash Equivalents of the kinds described in clauses (a) through (c) of this definition. 

“Claims” is defined in Section 12.2 of this Agreement. 

  
 19 

 “Code” is the Uniform Commercial Code, as the same may, from time to time, be
enacted and in effect in the Commonwealth of Massachusetts; provided, that, to the extent that the Code is used to define any term herein or in any Loan Document and such term is defined differently in different Articles or Divisions of the Code,
the definition of such term contained in Article or Division 9 shall govern; provided further, that in the event that, by reason of mandatory provisions of law, any or all of the attachment, perfection, or priority of, or remedies with respect to,
Bank’s Lien on any Collateral is governed by the Uniform Commercial Code in effect in a jurisdiction other than the Commonwealth of Massachusetts, the term “Code” shall mean the Uniform Commercial Code as enacted and in effect
in such other jurisdiction solely for purposes of the provisions thereof relating to such attachment, perfection, priority, or remedies and for purposes of definitions relating to such provisions. 

“Collateral” is any and all properties, rights and assets of Borrower described on Exhibit A. 

“Collateral Account” is any Deposit Account, Securities Account, or Commodity Account. 

“Commodity Account” is any “commodity account” as defined in the Code with such additions to such term as may
hereafter be made. 
 “Compliance Certificate” is attached as Exhibit B. 

“Contingent Obligation” is, for any Person, any direct or indirect liability, contingent or not, of that Person for
(a) any indebtedness, lease, dividend, letter of credit or other obligation of another such as an obligation directly or indirectly guaranteed, endorsed, co-made, discounted or sold with recourse by that Person, or for which that Person is
directly or indirectly liable; (b) any obligations for undrawn letters of credit for the account of that Person; and (c) all obligations from any interest rate, currency or commodity swap agreement, interest rate cap or collar agreement,
or other agreement or arrangement designated to protect a Person against fluctuation in interest rates, currency exchange rates or commodity prices; but “Contingent Obligation” does not include endorsements in the ordinary course of
business. The amount of a Contingent Obligation is the stated or determined amount of the primary obligation for which the Contingent Obligation is made or, if not determinable, the maximum reasonably anticipated liability for it determined by the
Person in good faith; but the amount may not exceed the maximum of the obligations under any guarantee or other support arrangement. 

“Control Agreement” is any control agreement entered into among the depository institution at which Borrower maintains a
Deposit Account or the securities intermediary or commodity intermediary at which Borrower maintains a Securities Account or a Commodity Account, Borrower, and Bank pursuant to which Bank obtains control (within the meaning of the Code) over such
Collateral Account. 
 “Copyrights” are any and all copyright rights, copyright applications, copyright registrations and
like protections in each work of authorship and derivative work thereof, whether published or unpublished and whether or not the same also constitutes a trade secret. 

“Credit Extension” is any Mezzanine Term Loan or any other extension of credit by Bank for Borrower’s benefit. 

“Default Rate” is defined in Section 2.2(b). 

“Deposit Account” is any “deposit account” as defined in the Code with such additions to such term as may hereafter
be made. 
 “Dollar Equivalent” is, at any time, (a) with respect to any amount denominated in Dollars, such amount,
and (b) with respect to any amount denominated in a Foreign Currency, the equivalent amount therefor in Dollars as determined by Bank at such time on the basis of the then-prevailing rate of exchange in San Francisco, California, for sales of
the Foreign Currency for transfer to the country issuing such Foreign Currency. 
 “Dollars,” “dollars” or
use of the sign “$” means only lawful money of the United States and not any other currency, regardless of whether that currency uses the “$” sign to denote its currency or may be readily converted into lawful money of the
United States. 

  
 20 

 “Draw Period” is the period of time commencing on the Effective Date and
continuing through the earliest to occur of (a) March 31, 2014 and (b) an Event of Default. 
 “Effective Date”
is defined in the preamble hereof. 
 “Equipment” is all “equipment” as defined in the Code with such additions
to such term as may hereafter be made, and includes without limitation all machinery, fixtures, goods, vehicles (including motor vehicles and trailers), and any interest in any of the foregoing. 

“ERISA” is the Employee Retirement Income Security Act of 1974, and its regulations. 

“Events of Default” are set forth in Section 8 of this Agreement. 

“Exchange Act” is the Securities Exchange Act of 1934, as amended. 

“Final Payment” is defined in Section 2.3(c). 

“Final Payment Percentage” is, for each Mezzanine Term Loan, three percent (3.0%). 

“Foreign Currency” means lawful money of a country other than the United States. 

“Funding Date” is any date on which a Mezzanine Term Loan is made to or for the account of Borrower, which shall be a
Business Day. 
 “GAAP” is generally accepted accounting principles set forth in the opinions and pronouncements of the
Accounting Principles Board of the American Institute of Certified Public Accountants and statements and pronouncements of the Financial Accounting Standards Board or in such other statements by such other Person as may be approved by a significant
segment of the accounting profession, which are applicable to the circumstances as of the date of determination. 
 “Governmental
Approval” is any consent, authorization, approval, order, license, franchise, permit, certificate, accreditation, registration, filing or notice, of, issued by, from or to, or other act by or in respect of, any Governmental Authority. 

“Governmental Authority” is any nation or government, any state or other political subdivision thereof, any agency,
authority, instrumentality, regulatory body, court, central bank or other entity exercising executive, legislative, judicial, taxing, regulatory or administrative functions of or pertaining to government, any securities exchange and any
self-regulatory organization. 
 “Inc.” is defined in the preamble of this Agreement. 

“Indebtedness” is (a) indebtedness for borrowed money or the deferred price of property or services, such as
reimbursement and other obligations for surety bonds and letters of credit, (b) obligations evidenced by notes, bonds, debentures or similar instruments, (c) capital lease obligations and (d) Contingent Obligations. 

“Indemnified Person” is defined in Section 12.2 of this Agreement. 

“Insolvency Proceeding” is any proceeding by or against any Person under the United States Bankruptcy Code, or any other
bankruptcy or insolvency law, including assignments for the benefit of creditors, compositions. extensions generally with its creditors, or proceedings seeking reorganization, arrangement, or other relief. 

“Intellectual Property” means all of Borrower’s right, title, and interest in and to the following: 

(a) its Copyrights, Trademarks and Patents; 

(b) any and all trade secrets and trade secret rights, including, without limitation, any rights to unpatented inventions, know-how, operating
manuals; 

  
 21 

 (c) any and all source code; 

(d) any and all design rights which may be available to Borrower; 

(e) any and all claims for damages by way of past, present and future infringement of any of the foregoing, with the right, but not the
obligation, to sue for and collect such damages for said use or infringement of the Intellectual Property rights identified above; and 

(f) all amendments, renewals and extensions of any of the Copyrights, Trademarks or Patents. 

“Inventory” is all “inventory” as defined in the Code in effect on the Effective Date with such additions to such
term as may hereafter be made, and includes without limitation all merchandise, raw materials, parts, supplies, packing and shipping materials, work in process and finished products, including without limitation such inventory as is temporarily out
of Borrower’s custody or possession or in transit and including any returned goods and any documents of title representing any of the above. 

“Investment” is any beneficial ownership of (including stock, membership interests, partnership interest or other securities)
any Person, or any loan, advance or capital contribution to any Person. 
 “IP Agreement” is collectively, (a) that
certain Intellectual Property Security Agreement dated as of the Effective Date between Inc. and Bank in connection with this Agreement and (b) that certain Intellectual Property Security Agreement dated as of the Effective Date between LLC and
Bank in connection with this Agreement, as each may be amended, modified or restated from time to time. 
 “IPO” is the
initial, underwritten offering and sale of Inc.’s securities to the public pursuant to an effective registration statement under the Securities Act of 1933, as amended. 

“Letter of Credit” means a standby letter of credit issued by Bank or another institution based upon an application,
guarantee, indemnity or similar agreement on the part of Bank. 
 “Lien” is a claim, mortgage, deed of trust, levy, charge,
pledge, security interest or other encumbrance of any kind, whether voluntarily incurred or arising by operation of law or otherwise against any property. 

“LLC” is defined in the preamble of this Agreement. 

“Loan Documents” are, collectively, this Agreement, the Senior Loan Agreement, the Warrant, the IP Agreement, the Perfection
Certificate, the SVB Control Agreement, any Bank Services Agreement, the Borrowing Resolutions, any subordination agreements, any note, or notes or guaranties executed by Borrower, and any other present or future agreement between Borrower and/or
for the benefit of Bank, all as amended, restated, or otherwise modified. 
 “Material Adverse Change” is: (a) a
material impairment in the perfection or priority of Bank’s Lien in the Collateral or in the value of such Collateral; (b) a material adverse change in the business, operations, or condition (financial or otherwise) of Borrower; or
(c) a material impairment of the prospect of repayment of any portion of the Obligations. 
 “Mezzanine Term Loan” and
“Mezzanine Term Loans” are each defined in Section 2.1.1(a). 
 “Mezzanine Term Loan Amortization
Date” is the date that is the first ( 1st) Payment Date following the two (2) year anniversary of the Effective Date (or, if the two (2) year anniversary is on the Payment Date
of a month, such date). 
 “Mezzanine Term Loan Maturity Date” is the Payment Date that is twenty-three (23) months
after the Mezzanine Term Loan Amortization Date. 
 “Obligations” are Borrower’s obligations to pay when due any
debts, principal, interest, Bank Expenses and other amounts Borrower owes Bank now or later, whether under this Agreement, the Loan Documents (other 

  
 22 

 
than the Warrant), or otherwise, including, without limitation, any interest accruing after Insolvency Proceedings begin and debts, liabilities, or obligations of Borrower assigned to Bank, and
to perform Borrower’s duties under the Loan Documents (other than the Warrant). 
 “Operating Documents” are, for any
Person, such Person’s formation documents, as certified with the Secretary of State of such Person’s state of formation on a date that is no earlier than thirty (30) days prior to the Effective Date, and, (a) if such Person is a
corporation, its bylaws in current form, (b) if such Person is a limited liability company, its limited liability company agreement (or similar agreement), and (c) if such Person is a partnership, its partnership agreement (or similar
agreement), each of the foregoing with all current amendments or modifications thereto. 
 “Patents” means all patents,
patent applications and like protections including without limitation improvements, divisions, continuations, renewals, reissues, extensions and continuations-in-part of the same. 

“Payment/Advance Form” is that certain form attached hereto as Exhibit C. 

“Payment Date” is the first (1st) calendar day of each month. 

“Perfection Certificate” is defined in Section 5.1 of this Agreement. 

“Permitted Accounts” is defined in Section 6.5(a) of this Agreement. 

“Permitted Indebtedness” is: 

(a) Borrower’s Indebtedness to Bank under this Agreement and the other Loan Documents; 

(b) Indebtedness existing on the Effective Date which is shown on the Perfection Certificate; 

(c) Subordinated Debt; 

(d) unsecured Indebtedness to trade creditors incurred in the ordinary course of business; 

(e) Indebtedness incurred as a result of endorsing negotiable instruments received in the ordinary course of business; 

(f) Indebtedness secured by Liens permitted under clauses (a) and (c) of the definition of “Permitted Liens” hereunder;
and 
 (g) extensions, refinancings, modifications, amendments and restatements of any items of Permitted Indebtedness (a) through
(f) above, provided that the principal amount thereof is not increased or the terms thereof are not modified to impose more burdensome terms upon Borrower or its Subsidiary, as the case may be. 

“Permitted Investments” are: 

(a) Investments (including, without limitation, Subsidiaries) existing on the Effective Date which are shown on the Perfection Certificate
(but specifically excluding any future Investments in any Subsidiaries unless otherwise permitted hereunder); 
 (b) Investments consisting
of Cash Equivalents; 
 (c) Investments consisting of the endorsement of negotiable instruments for deposit or collection or similar
transactions in the ordinary course of Borrower; 
 (d) Investments consisting of deposit or securities accounts maintained with Bank or
Bank’s Affiliates in which Bank has a first priority perfected security interest; 
 (e) Investments accepted in connection with
Transfers permitted by Section 7.1 of this Agreement; 

  
 23 

 (f) Investments (i) by a Borrower in another Borrower, and (ii) by a Subsidiary that is
not a Borrower in other Subsidiaries or in Borrower; 
 (g) Investments consisting of (i) travel advances and employee relocation loans
and other employee loans and advances in the ordinary course of business, and (ii) loans to employees, officers or directors relating to the purchase of equity securities of Borrower or its Subsidiaries pursuant to employee stock purchase plans
or agreements approved by Borrower’s board of directors; 
 (h) Investments (including debt obligations) received in connection with
the bankruptcy or reorganization of customers or suppliers and in settlement of delinquent obligations of, and other disputes with, customers or suppliers arising in the ordinary course of business; 

(i) Investments consisting of notes receivable of, or prepaid royalties and other credit extensions, to customers and suppliers who are not
Affiliates, in the ordinary course of business; provided that this paragraph (i) shall not apply to Investments of Borrower in any Subsidiary; and 

(j) joint ventures or strategic alliances in the ordinary course of Borrower’s business consisting of the non-exclusive licensing of
technology, the development of technology or the providing of technical support, but in no event consisting of cash investments by Borrower. 

“Permitted Liens” are: 

(a) Liens existing on the Effective Date which are shown on the Perfection Certificate or arising under this Agreement and the other Loan
Documents; 
 (b) Liens for taxes, fees, assessments or other government charges or levies, either (i) not due and payable or
(ii) being contested in good faith and for which Borrower maintains adequate reserves on Borrower’s Books, provided that no notice of any such Lien has been filed or recorded under the Internal Revenue Code of 1986, as amended, and
the Treasury Regulations adopted thereunder; 
 (c) purchase money Liens or capital leases (i) on Equipment acquired or held by
Borrower incurred for financing the acquisition of the Equipment securing no more than One Hundred Thousand Dollars ($100,000.00) in the aggregate amount outstanding, or (ii) existing on Equipment when acquired, if the Lien is confined
to the property and improvements and the proceeds of the Equipment; 
 (d) Liens of carriers, warehousemen, suppliers, or other Persons that
are possessory in nature arising in the ordinary course of business so long as such Liens attach only to Inventory, securing liabilities in the aggregate amount not to exceed One Hundred Thousand Dollars ($100,000.00) and which are not delinquent or
remain payable without penalty or which are being contested in good faith and by appropriate proceedings which proceedings have the effect of preventing the forfeiture or sale of the property subject thereto; 

(e) Liens to secure payment of workers’ compensation, employment insurance, old-age pensions, social security and other like obligations
incurred in the ordinary course of business (other than Liens imposed by ERISA); 
 (f) Liens incurred in the extension, renewal or
refinancing of the indebtedness secured by Liens described in (a) through (c), but any extension, renewal or replacement Lien must be limited to the property encumbered by the existing Lien and the principal amount of the indebtedness
may not increase; 
 (g) leases or subleases of real property granted in the ordinary course of Borrower’s business (or, if referring
to another Person, in the ordinary course of such Person’s business), and leases, subleases, non-exclusive licenses or sublicenses of personal property (other than Intellectual Property) granted in the ordinary course of Borrower’s
business (or, if referring to another Person, in the ordinary course of such Person’s business), if the leases, subleases, licenses and sublicenses do not prohibit granting Bank a security interest therein; 

(h) non-exclusive license of Intellectual Property granted to third parties in the ordinary course of business; 

  
 24 

 (i) Liens arising from attachments or judgments, orders, or decrees in circumstances not
constituting an Event of Default under Sections 8.4 and 8.7 of this Agreement; 
 (j) easements, reservations, rights-of-way, restrictions,
minor defects or irregularities in title and other similar Liens affecting real property not interfering in any material respect with the ordinary course of the business of Borrower; 

(k) deposits to secure the performance of real property leases incurred in the ordinary course of business and not representing an obligation
for borrowed money so long as each such deposit: (1) is made at the commencement of a lease or its renewal when there is no underlying default under such lease, and (2) is in an amount not exceeding One Hundred Thousand Dollars
($100,000.00); and 
 (l) Liens in favor of other financial institutions arising in connection with Borrower’s deposit and/or
securities accounts held at such institutions, provided that Bank has a first priority perfected security interest in the amounts held in such deposit and/or securities accounts and such accounts are permitted pursuant to the terms of this
Agreement. 
 “Person” is any individual, sole proprietorship, partnership, limited liability company, joint venture,
company, trust, unincorporated organization, association, corporation, institution, public benefit corporation, firm, joint stock company, estate, entity or government agency. 

“Prepayment Premium” shall be, with respect to each Mezzanine Term Loan, an additional fee payable to Bank in an amount equal
to, for a prepayment of any Mezzanine Term Loan made (a) on or prior to the first (1st) anniversary of the Funding Date of such Mezzanine Term Loan, three percent (3.0%) of the amount
prepaid, (b) after the first (1st) anniversary of the Funding Date of such Mezzanine Term Loan but on or prior to the second
(2nd) anniversary of the Funding Date of such Mezzanine Term Loan, two percent (2.0%) of the amount prepaid and (c) after the second
(2nd) anniversary of the Funding Date of such Mezzanine Term Loan, one percent (1.0%) of the amount prepaid. Notwithstanding the foregoing, Bank agrees to waive the Prepayment Premium if
(i) this Agreement is terminated and the Mezzanine Term Loans are prepaid in full in accordance with Section 2.1.1(d) of this Agreement in connection and simultaneously with the closing of an IPO or (ii) Bank agrees to refinance and
re document the Mezzanine Term Loans under another division of Bank (in its sole and exclusive discretion) prior to the Mezzanine Term Loan Maturity Date. 

“Rapid7 UK” is Rapid7 Ltd., Borrower’s wholly-owned Subsidiary organized under the laws of England and Wales. 

“Reconciliation Period” is each calendar month. 

“Registered Organization” is any “registered organization” as defined in the Code with such additions to such term
as may hereafter be made. 
 “Requirement of Law” is as to any Person, the organizational or governing documents of such
Person, and any law (statutory or common), treaty, rule or regulation or determination of an arbitrator or a court or other Governmental Authority, in each case applicable to or binding upon such Person or any of its property or to which such Person
or any of its property is subject. 
 “Responsible Officer” is any of the Chief Executive Officer, President, Chief
Financial Officer and Controller of Borrower. 
 “Restricted License” is any material license or other agreement with
respect to which Borrower is the licensee (a) that prohibits or otherwise restricts Borrower from granting a security interest in Borrower’s interest in such license or agreement or any other property, or (b) for which a default under
or termination of could interfere with Bank’s right to sell any Collateral. 
 “SEC” shall mean the Securities and
Exchange Commission, any successor thereto, and any analogous Governmental Authority. 

  
 25 

 “Securities Account” is any “securities account” as defined in the
Code with such additions to such term as may hereafter be made. 
 “Senior Loan Agreement” is that certain Loan and
Security Agreement by and between Bank and Borrower dated as of April 22, 2013, as amended, restated, modified, or supplemented from time to time. 

“Subordinated Debt” is indebtedness incurred by Borrower subordinated to all of Borrower’s now or hereafter indebtedness
to Bank (pursuant to a subordination, intercreditor, or other similar agreement in form and substance satisfactory to Bank entered into between Bank and the other creditor), on terms acceptable to Bank. 

“Subsidiary” is, as to any Person, a corporation, partnership, limited liability company or other entity of which shares of
stock or other ownership interests having ordinary voting power (other than stock or such other ownership interests having such power only by reason of the happening of a contingency) to elect a majority of the board of directors or other managers
of such corporation, partnership or other entity are at the time owned, or the management of which is otherwise controlled, directly or indirectly through one or more intermediaries, or both, by such Person. Unless the context otherwise requires,
each reference to a Subsidiary herein shall be a reference to a Subsidiary of Borrower. 
 “SVB Control Agreement” is, for
each Borrower, that certain Securities Account Control Agreement by and among SVB Securities, Apex Clearing Corporation, such Borrower and Bank. 

“Trademarks” means any trademark and servicemark rights, whether registered or not, applications to register and
registrations of the same and like protections, and the entire goodwill of the business of Borrower connected with and symbolized by such trademarks. 

“Transfer” is defined in Section 7.1 of this Agreement. 

“Warrant” is, collectively, (a) that certain Warrant to Purchase Stock dated as of the Effective Date between Inc. and
Bank and (b) that certain Warrant to Purchase Stock dated as of the Effective Date between Inc. and WestRiver Mezzanine Loans, LLC, in each case as may be amended, restated, modified, or supplemented from time to time. 

[Signature page follows.] 

  
 26 

 IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be executed as a sealed
instrument under the laws of the Commonwealth of Massachusetts as of the Effective Date. 
  

			
	BORROWER
	
	RAPID7 LLC
		
	By:		 /s/ Steven Gatoff

	Name:		Steven Gatoff
	Title:		Chief Financial Officer
	
	RAPID7, INC.
		
	By:		 /s/ Steven Gatoff

	Name:		Steven Gatoff
	Title:		Chief Financial Officer
	
	BANK
	
	SILICON VALLEY BANK
		
	By:		  

	Name:		  

	Title:		  

  
 27 

 IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be executed as a sealed
instrument under the laws of the Commonwealth of Massachusetts as of the Effective Date. 
  

			
	BORROWER
	
	RAPID7 LLC
		
	By:		  

	Name:		  

	Title:		  

	
	RAPID7, INC.
		
	By:		  

	Name:		  

	Title:		  

	
	BANK
	
	SILICON VALLEY BANK
		
	By:		 /s/ Brendan P. Quinn

	Name:		 Brendan P. Quinn

	Title:		 Vice President

  
 28 

 EXHIBIT A 

The Collateral consists of all of Borrower’s right, title and interest in and to the following: 

All goods, equipment, inventory, contract rights or rights to payment of money, leases, license agreements, franchise agreements, general
intangibles (including payment intangibles), accounts (including health-care receivables), documents, instruments (including any promissory notes), chattel paper (whether tangible or electronic), cash, deposit accounts, all certificates of deposit,
fixtures, letters of credit rights (whether or not the letter of credit is evidenced by a writing), commercial tort claims, securities, and all other investment property, supporting obligations, and financial assets, whether now owned or hereafter
acquired, wherever located; and any copyright rights, copyright applications, copyright registrations and like protections in each work of authorship and derivative work, whether published or unpublished, now owned or later acquired; any patents,
trademarks, service marks and applications therefor; trade styles, trade names, any trade secret rights, including any rights to unpatented inventions, know-how, operating manuals, license rights and agreements and confidential information, now
owned or hereafter acquired; or any claims for damages by way of any past, present and future infringement of any of the foregoing; and 

All Borrower’s books relating to the foregoing and any and all claims, rights and interests in any of the above and all substitutions
for, additions, attachments, accessories, accessions and improvements to and replacements, products, proceeds and insurance proceeds of any or all of the foregoing. 

Notwithstanding the foregoing, the Collateral does not include more than sixty-five percent (65.0%) of the presently existing and
hereafter arising issued and outstanding shares of capital stock owned by Borrower of any Foreign Subsidiary which shares entitle the holder thereof to vote for directors or any other matter. A “Foreign Subsidiary” means any Subsidiary
that is not organized under the laws of the United States or any state or territory thereof or the District of Columbia. 

 EXHIBIT B 

COMPLIANCE CERTIFICATE 
  

					
	TO:	  	SILICON VALLEY BANK	  	Date:                     
	FROM:	  	RAPID7, INC. and RAPID7 LLC	  	

 The undersigned authorized officer of RAPID7, INC. and RAPID7 LLC (“Borrower”) certifies that under
the terms and conditions of the Subordinated Loan and Security Agreement between Borrower and Bank (the “Agreement”): 
 (1)
Borrower is in complete compliance for the period ending                      with all required covenants except as noted below; (2) there are
no Events of Default; (3) all representations and warranties in the Agreement are true and correct in all material respects on this date except as noted below; provided, however, that such materiality qualifier shall not be applicable to any
representations and warranties that already are qualified or modified by materiality in the text thereof; and provided, further that those representations and warranties expressly referring to a specific date shall be true, accurate and complete in
all material respects as of such date; (4) Borrower, and each of its Subsidiaries, has timely filed all required tax returns and reports, and Borrower has timely paid all foreign, federal, state and local taxes, assessments, deposits and
contributions owed by Borrower except as otherwise permitted pursuant to the terms of Section 5.8 of the Agreement; and (5) no Liens have been levied or claims made against Borrower or any of its Subsidiaries relating to unpaid employee
payroll or benefits of which Borrower has not previously provided written notification to Bank. 
 Attached are the required documents
supporting the certification. The undersigned certifies that these are prepared in accordance with GAAP consistently applied from one period to the next except as explained in an accompanying letter or footnotes. The undersigned acknowledges that no
borrowings may be requested at any time or date of determination that Borrower is not in compliance with any of the terms of the Agreement, and that compliance is determined not just at the date this certificate is delivered. Capitalized terms used
but not otherwise defined herein shall have the meanings given them in the Agreement. 
 Please indicate compliance status by circling Yes/No under
“Complies” column. 
  

							
	 Reporting Covenants
	  	 Required
	  	 Complies

				
	Monthly financial statements with Compliance Certificate	  	Monthly within 30 days	  	Yes	  	No
	Annual financial statement (CPA Audited)	  	FYE within 180 days	  	Yes	  	No
	lO-Q, 10-K and 8-K	  	Within 5 days after filing with SEC	  	Yes	  	No
	Board-approved projections	  	Earlier of FYE within 60 days or 10 days following board approval	  	Yes	  	No
	
	The following Intellectual Property was registered (or a registration application submitted) after the Effective Date (if no registrations, state “None”)
	  

	  

 Other Matters 
  

					
	Have there been any amendments of or other changes to the capitalization table of Borrower and to the Operating Documents of Borrower or any of its Subsidiaries? If yes, provide copies of any such amendments or changes with this
Compliance Certificate.	  	Yes	  	No

 The following are the exceptions with respect to the certification above: (If no exceptions
exist, state “No exceptions to note.”) 
  
  

 
  
  

									
	RAPID7, INC.				BANK USE ONLY
	RAPID7, LLC						
					Received by:		  

									AUTHORIZED SIGNER
	By:		  
						
	Name:		  
				Date:		  

	Title:		  
						
							Verified:		  

									AUTHORIZED SIGNER
							Date:		  

				
							Compliance Status:             Yes    No

 EXHIBIT C 

LOAN PAYMENT/ADVANCE REQUEST FORM 

DEADLINE FOR SAME DAY PROCESSING IS
NOON EASTERN TIME 
  

			
	Fax To:		Date:                     

  

			
	  LOAN PAYMENT:		
	RAPID7, INC. and RAPID7 LLC
		
	  From Account
#                                         
                                   		To Account #                                  
                                         
  
	(Deposit Account #)		(Loan Account #)
		
	  Principal $
                                         
                                         
  		and/or Interest $
                                         
                               
		
	  Authorized Signature:
                                         
               		Phone Number:
                                         
               
	  Print Name/Title:
                                         
                      		

  

 

			
	  LOAN ADVANCE:		
	
	 Complete Outgoing Wire Request section below if all or a portion of the funds from this loan advance are for an outgoing
wire.

		
	  From Account
#                                         
                                   		To Account
#                                         
                                    
	(Loan Account #)		(Deposit Account #)
	
	  Amount of Mezzanine Term Loan
$                                         
                           

 All Borrower’s representations and warranties in the Subordinated Loan and Security
Agreement are true, correct and complete in all material respects on the date of the request for an advance; provided, however, that such materiality qualifier shall not be applicable to any representations and warranties that already are qualified
or modified by materiality in the text thereof; and provided, further that those representations and warranties expressly referring to a specific date shall be true, accurate and complete in all material respects as of such date: 

			
	  Authorized Signature:
                                         
               		Phone Number:
                                         
               
	  Print Name/Title:
                                         
                      		

  

 

			
	  OUTGOING WIRE REQUEST:		
	  Complete only if all or a portion of funds from the loan advance above is to be wired.
	  Deadline for same day processing is noon, Eastern Time
		
	  Beneficiary Name:
                                         
                              		Amount of Wire:
$                                         
                           
	  Beneficiary Bank:
                                         
                               		Account Number:
                                         
                            
	  City and State:
                                         
                           		
		
	  Beneficiary Bank Transit (ABA) #:
                                   		Beneficiary Bank Code (Swift, Sort, Chip, etc.):                     
			 (For International Wire Only)

		
	  Intermediary Bank:
                                         
                   		Transit (ABA) #:
                                         
                             
	  For Further Credit to:
                                         
                                         
                                         
                                         
        
	
	  Special Instruction:
                                         
                                         
                                         
                                         
           

  

 
By signing below, I (we) acknowledge and agree that my (our) funds transfer request shall be processed in accordance with
and subject to the terms and conditions set forth in the agreements(s) covering funds transfer service(s), which agreements(s) were previously received and executed by me (us). 

 

			
	  Authorized Signature:                                
                                 		2nd Signature (if required):
                                         
                 
	  Print Name/Title:                                
                                        		Print Name/Title:                                  
                                       
	  Telephone #:
                                         
                   		Telephone #:

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00246-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00246-of-00352.parquet"}]]