8-K

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d)

of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): August 18, 2015

Rapid7, Inc.

(Exact name of registrant as specified in its charter)

Delaware	001-37496	35-2423994
(State or other jurisdiction of incorporation)	(Commission File Number)	(IRS Employer Identification No.)
100 Summer Street, Boston, Massachusetts		02110
(Address of principal executive offices)		(Zip Code)

Registrant’s telephone number, including area code: (617) 247-1717

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

¨ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

¨ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

¨ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

¨ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Item 2.02 Results of Operations and Financial Condition.

On August 18, 2015, Rapid7, Inc. (the “Company”) issued a press release announcing its financial results for the second quarter ended June 30, 2015. The Company’s press release is furnished as Exhibit 99.1 to this Current Report on Form 8-K.

Item 7.01 Regulation FD Disclosure.

In connection with the announcement of the Company’s financial results for the second quarter ended June 30, 2015, the Company is furnishing as Exhibits 99.2 and 99.3 to this Current Report on Form 8-K presentations that the Company may use from time to time. These presentations will also be posted on the investor relations section of the Company’s website.

The information included in this Current Report on Form 8-K and the exhibits attached hereto shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”) or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, regardless of any general incorporation language in such filing.

Item 9.01 Financial Statements and Exhibits.

(d) Exhibits

Exhibit No.	Description
99.1	Second Quarter 2015 Financial Results Press Release, dated August 18, 2015.
99.2	Company Presentation, dated August 18, 2015.
99.3	Second Quarter 2015 Financial Results Presentation, dated August 18, 2015.

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the Registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

	Rapid7, Inc.
Dated: August 18, 2015
	By:	/s/ Steven Gatoff
		Steven Gatoff
		Chief Financial Officer

EXHIBIT INDEX

Exhibit No.	Description
99.1	Second Quarter 2015 Financial Results Press Release, dated August 18, 2015.
99.2	Company Presentation, dated August 18, 2015.
99.3	Second Quarter 2015 Financial Results Presentation, dated August 18, 2015.

EX-99.1

Exhibit 99.1

RAPID7 ANNOUNCES SECOND QUARTER 2015 FINANCIAL RESULTS

Boston, MA – August 18, 2015 – Rapid7, Inc. (NASDAQ: RPD), a leading provider of security data and analytics solutions, today announced its financial results for the second quarter of 2015.

“Our strong second quarter results reflect the increased need for a data and analytics-driven approach to cyber security. As a result we saw significant ongoing customer adoption through the first half of 2015,” said Corey Thomas, president and chief executive officer of Rapid7. “At the same time, recent additions to our product and services portfolios – for example the addition of AppSpider for web application testing and our new Incident Response services – are enabling us to help our customers tackle a broader set of security challenges. We’re excited to extend these customer relationships and help them gain the insight that they need to address their complex security challenges.”

“Our solid second quarter financial results demonstrate the continued momentum in our business, with revenue growing 44% year-over-year on strong customer demand. Our subscription and ratable revenue model provide us with a high degree of recurring revenue and meaningful visibility,” said Steven Gatoff, chief financial officer of Rapid7. “We were pleased to see another quarter of increasing renewal rates in the second quarter and strong deferred revenue growth of 45% as we continue to execute on our growth strategy.”

Second Quarter 2015 Financial Highlights

• Strong Revenue Growth: Total revenue grew for both products and services, driven by strong customer demand across both enterprise and mid-market customers. For the second quarter of 2015, total revenue was $25.8 million, an increase of 44% year-over-year.

• Continued Deferred Revenue Growth and High Revenue Visibility: Total deferred revenue at the end of the second quarter was $97.5 million, increasing 45% year-over-year. Approximately 83% of total revenue for the second quarter of 2015 came from deferred revenue as of the beginning of the quarter.

• Solid Base of Recurring Revenue: 61% of total revenue in the second quarter of 2015 was from subscription-based recurring revenue comprised of content subscriptions, maintenance & support, cloud-based subscriptions, and managed services subscriptions.

• Growth Across Geographies: For the second quarter of 2015, total revenue from North America increased 43% year-over-year to $22.6 million and comprised 88% of total revenue. Total revenue from international increased 51% year-over-year to $3.2 million and comprised 12% of total revenue for the second quarter of 2015.

• Continued Increases in Renewal Rates: The renewal rate for the second quarter of 2015, which includes upsells and cross-sells of additional products and services, increased to 115% from 108% in the second quarter of 2014, reflecting increasing customer uptake of existing and new Rapid7 products. The expiring revenue renewal rate, which excludes upsells and cross-sells of additional products and services, also improved to 87% in the second quarter of 2015 from 85% the previous year.

• Improved Gross Margins in Professional Services: Late 2014 and early 2015 investments in more strategic professional services have already began to yield positive results as professional services margin continued to increase and came in at 19% in the second quarter of 2015 compared to 15% in the second quarter of 2014.

• Non-GAAP Operating Loss and Loss Per Share: For the second quarter of 2015, GAAP operating loss was $8.6 million and non-GAAP operating loss was $7.1 million. GAAP net loss per share was $2.59 and non-GAAP net loss per share was $0.61 for the second quarter in 2015.

• Continued Improvements in Operating Cash Flow Leverage: For the second quarter of 2015, cash used in operations was $1.2 million compared to cash used in operations of $2.3 million in the second quarter of 2014.

Recent Business Highlights

Strong Continued Customer Momentum and Growth:

• Increased market adoption with new customer additions and expanded relationships with existing customers, and ended the second quarter of 2015 with more than 4,150 customers, an increase of 34% year-over-year.

• Added customers in both the enterprise and mid-market segments, and increased penetration into Fortune 1000 customers, including BJ’s Wholesale Club, Boyd Gaming, Dollar Tree, Fastenal Company, Iowa State University, Johnson Controls, Massachusetts Mutual Life Insurance, Parker Hannifin, Pepco Holdings, Samsung Electronics, and the Smithsonian Institute.

Technology Platform and Product Innovation:

• Continued investment and innovation in Threat Exposure Management offering:

• Introduced the ability for customers to assess exposures across mobile devices alongside physical, virtual and cloud assets in the Nexpose product line.

• Acquired NT OBJECTives, a web and mobile application security testing company, in April 2015, expanding Rapid7’s Threat Exposure Management offerings to further meet the needs of modern business infrastructures. The new web application scanning solution, AppSpider, is now part of the Rapid7 portfolio, enhancing Rapid7’s deep analysis and security testing capabilities to help customers manage risk across web applications and assets.

• Delivered the first phase of integration of the AppSpider product and the Nexpose product so that customers can integrate data sets for centralized analytics and remediation planning.

• Named Best Vulnerability Assessment provider by security professionals in the SANS Institute’s Best of 2014 Awards, which were recently announced. Rapid7’s Threat Exposure Management solutions provide information security teams with the capability to assess, prioritize, and more quickly mitigate risk across their environments, from endpoint to the cloud.

• Continued to build traction with intruder analytics solution, UserInsight:

• Introduced European hosting option for UserInsight to help organizations meet their regional data hosting compliance requirements. Driven by market demand, UserInsight customers can now choose to host data in Germany, as an alternative to the United States. UserInsight can provide visibility into intruder behavior across an organization’s ecosystem, from the endpoint to the cloud.

• Introduced the capability in UserInsight to detect phishing attacks as they occur in a network to provide an early warning system for an attack.

• Continued evolution and global roll-out of Strategic Professional Services

• Launched Strategic Advisory Services in EMEA to help security executives and teams solve pressing cyber security challenges. The practice helps organizations transform their security programs to be more relevant, actionable, and sustainable through data-driven, risk-based analysis.

• Also announced that Rapid7 will offer a new global service, Threat Modeling, to help organizations identify potential threats against applications, systems, and infrastructures during their design phase.

Continued Robust Technology Partnerships with Industry Leaders:

• Further expanded the Rapid7 Partner ecosystem by adding new technology integration partnerships to continue to build synergy and leverage across the IT and security landscape.

• Expanded Rapid7’s intruder analytics solution, UserInsight, to integrate and consume data from Microsoft Office 365 enhancing the breadth of data collected by the Rapid7 Security Data & Analytics platform. Security teams and incident responders can detect and investigate incidents from the endpoint to the cloud, now including attacks that may impact or originate in Microsoft Office 365.

Third Quarter and Full-Year 2015 Guidance

Rapid7 anticipates total revenue, non-GAAP operating loss, and non-GAAP net loss per share to be in the following ranges:

Third Quarter 2015:

Total revenue	$25.4 to $26.8 million
Operating loss (non-GAAP)	($10.9) to ($9.9) million
Net loss per share (non-GAAP)	($0.38) to ($0.35)

The third quarter net loss per share calculation assumes 33.0 million basic and diluted weighted average common shares outstanding.

Full-Year 2015:

Total revenue	$102 to $105 million
Operating loss (non-GAAP)	($35.4) to ($33.4) million
Net loss per share (non-GAAP)	($1.56) to ($1.48)

The full-year net loss per share calculation assumes 24.6 million basic and diluted weighted average common shares outstanding. Guidance for the third quarter and full-year 2015 does not include any potential impact of any foreign exchange gains or losses.

Non-GAAP guidance excludes estimates for stock-based compensation expense, amortization of intangible assets and acquisition related expenses. A reconciliation of non-GAAP guidance measures to the most comparable GAAP measures is not available on a forward-looking basis. Rapid7 has provided a reconciliation of historical non-GAAP financial measures to the most comparable GAAP measures in the financial statement tables included in this press release.

Conference Call and Webcast Information

Rapid7 will host a conference call today to discuss its results at 5:00 p.m. Eastern Time. The call will be accessible by telephone at 800-755-1805 (domestic) or 212-231-2930 (international). The call will also be available live via webcast on the company’s web site at http://investors.rapid7.com. A telephone replay of the conference call will be available at 800-633-8284 or 402-977-9140 (access code 21772863) until August 21, 2015. A webcast replay will be available at http://investors.rapid7.com.

About Rapid7

Rapid7 is a leading provider of security data and analytics solutions that enable organizations to implement an active, analytics-driven approach to cyber security. We combine our extensive experience in security data and analytics and deep insight into attacker behaviors and techniques to make sense of the wealth of data available to organizations about their IT environments and users. Our solutions empower organizations to prevent attacks by providing visibility into vulnerabilities and to rapidly detect compromises, respond to breaches, and correct the underlying causes of attacks. Rapid7 is trusted by more than 4,150 organizations across 90 countries, including 34% of the Fortune 1000. To learn more about Rapid7 or get involved in our threat research, visit www.rapid7.com.

Non-GAAP Financial Measures

Rapid7 believes that the use of non-GAAP gross profit, non-GAAP operating loss and non-GAAP net loss is helpful to our investors. These measures, which we refer to as our non-GAAP financial measures, are not prepared in accordance with GAAP.

For the three and six months ended June 30, 2015 and 2014, non-GAAP gross profit, non-GAAP operating loss and non-GAAP net loss excluded stock-based compensation expense, amortization of intangible assets and acquisition related expenses.

Because of varying available valuation methodologies, subjective assumptions and the variety of equity instruments that can impact a company’s non-cash expense, Rapid7 believes that providing non-GAAP financial measures that exclude stock-based compensation expense allow for more meaningful comparisons between our operating results from period to period. Rapid7 also believes that excluding the impact of amortization of intangible assets allows for more meaningful comparisons between operating results from period to period as the intangible assets are valued at the time of acquisition and are amortized over a period of several years after the acquisition. Rapid7 also believes that excluding the impact of the costs directly related to acquisitions allows for a more meaningful comparison between operating results from period to period, as these costs are unrelated to the current operations and neither comparable to the prior period nor predictive of future results. Each of our non-GAAP financial measures is an important tool for financial and operational decision making and for evaluating our own operating results over different periods of time. The non-GAAP financial data are not measures of our financial performance under GAAP and should not be considered as alternatives to gross profit, operating loss, net loss or any other performance measures derived in accordance with GAAP. Non-GAAP financial measures may not provide information that is directly comparable to that provided by other companies in our industry, as other companies in our industry may calculate non-GAAP financial results differently, particularly related to non-recurring, unusual items. In addition, there are limitations in using non-GAAP financial measures because the non-GAAP financial measures are not prepared in accordance with GAAP, may be different from non-GAAP financial measures used by other companies and exclude expenses that may have a material impact on our reported financial results. Further, stock-based compensation expense has been, and will continue to be for the foreseeable future, a significant recurring expense in our business and an important part of the compensation provided to our employees. The presentation of non-GAAP financial information is not meant to be considered in isolation or as a substitute for the directly comparable

financial measures prepared in accordance with GAAP. Rapid7 urges investors to review the reconciliation of our non-GAAP financial measures to the comparable GAAP financial measures included below, and not to rely on any single financial measure to evaluate our business.

Cautionary Language Concerning Forward-Looking Statements

This press release includes forward-looking statements. All statements contained in this press release other than statements of historical facts, including, without limitation, statements regarding our future financial and business performance for the third quarter and full-year 2015, technical innovations, market opportunity and plans and objectives for future operations, are forward-looking statements. The words “anticipate,” believe,” “continue,” “estimate,” “expect,” “intend,” “may,” “will” and similar expressions are intended to identify forward-looking statements. We have based these forward-looking statements largely on our current expectations and projections about future events and financial trends that we believe may affect our financial condition, results of operations, business strategy, short-term and long-term business operations and objectives and financial needs. These forward-looking statements are subject to a number of risks and uncertainties, including, without limitation, risks related to our rapid growth and ability to sustain our revenue growth rate, the ability of our products and professional services to correctly detect vulnerabilities, competition in the markets in which we operate, market growth, our ability to innovate and manage our growth, our ability to operate in compliance with applicable laws and the risks and uncertainties set forth in the “Risk Factors” section of our prospectus filed pursuant to Rule 424(b)(4) under the Securities Act of 1933, as amended, on July 17, 2015, and subsequent reports that we file with the Securities and Exchange Commission. Moreover, we operate in a very competitive and rapidly changing environment. New risks emerge from time to time. It is not possible for our management to predict all risks, nor can we assess the impact of all factors on our business or the extent to which any factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements we may make. In light of these risks, uncertainties and assumptions, we cannot guarantee future results, levels of activity, performance, achievements or events and circumstances reflected in the forward-looking statements will occur. We are under no duty to update any of these forward-looking statements after the date of this press release to conform these statements to actual results or revised expectations, except as required by law. You should, therefore, not rely on these forward-looking statements as representing our views as of any date subsequent to the date of this press release.

Contact:

Rapid7 Investor Relations

857-415-4419

investors@rapid7.com

Rapid7, Inc.

Consolidated Balance Sheets

(Unaudited, in thousands)

	June 30, 2015			June 30, 2015 Pro Forma			December 31, 2014
Assets
Current assets:
Cash	$	27,000		$	140,921		$	36,823
Accounts receivable, net		26,363			26,363			25,412
Prepaid expenses and other current assets		6,297			4,161			4,209
Total current assets		59,660			171,445			66,444
Property and equipment, net		7,607			7,607			7,922
Goodwill		15,758			15,758			11,265
Intangible assets, net		2,767			2,767			1,156
Other assets		682			682			179
Total assets	$	86,474		$	198,259		$	86,966
Liabilities, Redeemable Convertible Preferred Stock and Stockholders’ Deficit
Current liabilities:
Accounts payable		2,990			2,990			3,536
Accrued expenses		12,765			12,155			11,907
Deferred revenue, current portion		66,040			66,040			58,164
Term loan payable, net of unamortized debt discount		3,976			3,976			—
Other current liabilities		991			991			642
Total current liabilities		86,762			86,152			74,249
Deferred revenue, non-current portion		31,471			31,471			26,892
Term loan payable, net of unamortized debt discount		13,172			13,172			16,871
Other long-term liabilities		5,050			5,050			4,218
Total liabilities		136,455			135,845			122,230
Commitments and contingencies
Redeemable convertible preferred stock:
Series A redeemable convertible preferred stock		83,200			—			68,892
Series B redeemable convertible preferred stock		6,854			—			5,681
Series C redeemable convertible preferred stock		91,215			—			80,286
Series D redeemable convertible preferred stock		65,390			—			56,739
Stockholders’ deficit:
Common stock		132			392			126
Additional paid-in-capital		—			372,955			—
Accumulated deficit		(293,246	)		(307,407	)		(243,462	)
Treasury stock		(3,526	)		(3,526	)		(3,526	)
Total stockholders’ deficit		(296,640	)		62,414			(246,862	)
Total liabilities, redeemable convertible preferred stock and stockholders’ deficit	$	86,474		$	198,259		$	86,966

Note: The unaudited pro forma balance sheet as of June 30, 2015 has been provided to reflect the pro forma effect of Rapid7, Inc.’s (the “Company”) initial public offering (the “IPO”), which occurred in July 2015, and assumes the following: (i) the conversion of the Company’s redeemable convertible preferred stock into common stock and related beneficial conversion charge of $14.2 million associated with the conversion of the Series D preferred stock into common stock, (ii) net proceeds from the IPO of $107.4 million after deducting the underwriting discount and estimated offering expenses, and (iii) net proceeds from the private placement issuance of $5.0 million that occurred concurrently with the IPO.

Rapid7, Inc.

Consolidated Statements of Operations

(Unaudited, in thousands, except share and per share data)

	Three Months Ended						Six Months Ended
	June 30, 2015			June 30, 2014			June 30, 2015			June 30, 2014
Revenue:
Products	$	14,639		$	11,013		$	28,284		$	21,628
Maintenance and support		6,253			4,474			12,052			8,619
Professional services		4,898			2,393			9,025			4,369
Total revenue		25,790			17,880			49,361			34,616
Cost of revenue:
Products		1,339			1,022			2,885			2,261
Maintenance and support		1,412			1,152			2,622			2,140
Professional services		3,976			2,036			7,712			3,667
Total cost of revenue		6,727			4,210			13,219			8,068
Total gross profit		19,063			13,670			36,142			26,548
Operating expenses:
Research and development		8,131			6,328			14,545			12,448
Sales and marketing		14,457			11,561			27,687			22,565
General and administrative		5,048			3,174			9,101			6,656
Total operating expenses		27,636			21,063			51,333			41,669
Loss from operations		(8,573	)		(7,393	)		(15,191	)		(15,121	)
Other income (expense), net:
Interest income (expense), net		(737	)		(703	)		(1,422	)		(1,398	)
Other income (expense), net		163			4			(142	)		45
Loss before income taxes		(9,147	)		(8,092	)		(16,755	)		(16,474	)
Provision for income taxes		97			95			171			191
Net loss		(9,244	)		(8,187	)		(16,926	)		(16,665	)
Accretion of preferred stock to redemption value		(23,788	)		(15,464	)		(35,061	)		(27,642	)
Net loss attributable to common stockholders, basic and diluted	$	(33,032	)	$	(23,651	)	$	(51,987	)	$	(44,307	)
Net loss per share attributable to common stockholders, basic and diluted	$	(2.59	)	$	(1.85	)	$	(4.10	)	$	(3.48	)
Weighted-average common shares outstanding, basic and diluted		12,745,051			12,762,938			12,693,900			12,740,052
Pro forma net loss per share attributable to common stockholders, basic and diluted	$	(0.60	)				$	(0.80	)
Pro forma weighted-average common shares outstanding, basic and diluted		38,797,656						38,746,505

Note: The unaudited pro forma net loss per share for the three and six months ended June 30, 2015 has been provided to reflect the pro forma effect of the Company’s IPO, which occurred in July 2015, and assumes the following: (i) the conversion of all outstanding shares of the Company’s redeemable convertible preferred stock into an aggregate of 18,322,605 shares of common stock as of the beginning of the period and (ii) the sale and issuance of 7,730,000 shares of common stock as of the beginning of the period. The amount recorded to reflect the beneficial conversion charge of $14.2 million associated with the conversion of the Company’s Series D preferred stock into common stock has been included and the amounts recorded to reflect the accretion of redeemable convertible preferred stock to redemption value has been added back to arrive at pro form net loss attributable to common stockholders.

Rapid7, Inc.

Consolidated Statements of Cash Flows

(unaudited, in thousands)

	Six Months Ended
	June 30, 2015			June 30, 2014
Cash flows from operating activities:
Net loss	$	(16,926	)	$	(16,665	)
Adjustments to reconcile net loss to cash used in operating activities:
Depreciation and amortization		2,361			2,024
Amortization of debt discount		276			276
Non-cash interest expense		51			—
Stock-based compensation expense		1,406			1,159
Provision for doubtful accounts		376			258
Foreign currency remeasurement loss		53			—
Change in operating assets and liabilities:
Accounts receivable		(840	)		1,433
Prepaid expenses and other assets		(1,067	)		(1,008	)
Accounts payable		(1,368	)		(1,181	)
Accrued expenses		(1,082	)		(532	)
Deferred revenue		12,425			7,533
Contingent consideration		—			46
Other liabilities		82			2,233
Net cash used in operating activities		(4,253	)		(4,424	)
Cash flows from investing activities:
Business acquisitions, net of cash acquired		(3,344	)		—
Purchases of property and equipment		(1,195	)		(5,890	)
Net cash used in investing activities		(4,539	)		(5,890	)
Cash flows from financing activities
Payments of initial public offering costs		(1,526	)		—
Payments of capital lease obligations		(123	)		(133	)
Payments of contingent consideration related to business acquisitions		—			(750	)
Proceeds from stock option exercises		705			80
Net cash used in financing activities		(944	)		(803	)
Effects of exchange rates on cash		(87	)		3
Net decrease in cash		(9,823	)		(11,114	)
Cash, beginning of period		36,823			20,612
Cash, end of period	$	27,000		$	9,498

Rapid7, Inc.

GAAP to Non-GAAP Reconciliation

(unaudited, in thousands, except share and per share data)

	Three Months Ended						Six Months Ended
	June 30, 2015			June 30, 2014			June 30, 2015			June 30, 2014
Total gross profit (GAAP)	$	19,063		$	13,670		$	36,142		$	26,548
Plus: Stock-based compensation expense1		52			47			101			86
Plus: Amortization of intangible assets2		276			217			479			434
Total gross profit (non-GAAP)	$	19,391		$	13,934		$	36,722		$	27,068
Gross margin (non-GAAP)		75	%		78	%		74	%		78	%
Loss from operations (GAAP)	$	(8,573	)	$	(7,393	)	$	(15,191	)	$	(15,121	)
Plus: Stock-based compensation expense1		831			631			1,406			1,159
Plus: Amortization of intangible assets2		276			217			479			434
Plus: Acquisition related expenses3		360			—			416			—
Loss from operations (non-GAAP)	$	(7,106	)	$	(6,545	)	$	(12,890	)	$	(13,528	)
Net loss attributable to common stockholders (GAAP)	$	(33,032	)	$	(23,651	)	$	(51,987	)	$	(44,307	)
Plus: Accretion of preferred stock to redemption value		23,788			15,464			35,061			27,642
Net loss (GAAP)		(9,244	)		(8,187	)		(16,926	)		(16,665	)
Plus: Stock-based compensation expense1		831			631			1,406			1,159
Plus: Amortization of intangible assets2		276			217			479			434
Plus: Acquisition related expenses3		360			—			416			—
Net loss (non-GAAP)	$	(7,777	)	$	(7,339	)	$	(14,625	)	$	(15,072	)
Net loss per share, basic and diluted (non-GAAP)	$	(0.61	)	$	(0.58	)	$	(1.15	)	$	(1.18	)
Weighted average shares used in GAAP and non-GAAP net loss per share, basic and diluted		12,745,051			12,762,938			12,693,900			12,740,052
1      Includes stock-based compensation expense as follows:
Cost of revenue	$	52		$	47		$	101		$	86
Research and development		266			122			410			242
Sales and marketing		195			197			310			316
General and administrative		318			265			585			515
2      Includes amortization of intangible assets as follows:
Cost of revenue	$	276		$	217		$	479		$	434
3      Includes acquisition related expenses as follows:
General and administrative	$	360		$	—		$	416		$	—

EX-99.2

Exhibit 99.2

SECURITY DATA & ANALYTICS

Company Overview

AUGUST 18, 2015 CONFIDENTIAL AND PROPRIETARY

Disclaimers

This presentation includes forward-looking statements. All statements contained in this presentation other than statements of historical facts, including statements regarding future results of operations and the financial position of Rapid7, Inc. (“Rapid7,” “we,” “us” or “our”) our business strategy and plans and our objectives for future operations, are forward-looking statements. The words “anticipate,” believe,” “continue,” “estimate,” “expect,” “intend,” “may,” “will” and similar expressions are intended to identify forward-looking statements. We have based these forward-looking statements largely on our current expectations and projections about future events and financial trends that we believe may affect our financial condition, results of operations, business strategy, short-term and long-term business operations and objectives, and financial needs. These forward-looking statements are subject to a number of risks and uncertainties, including, without limitation, those set forth in the “Risk Factors” section of our prospectus filed pursuant to Rule 424(b)(4) under the Securities Act of 1933, as amended, on July 17, 2015. Moreover, we operate in a very competitive and rapidly changing environment. New risks emerge from time to time. It is not possible for our management to predict all risks, nor can we assess the impact of all factors on our business or the extent to which any factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements we may make. In light of these risks, uncertainties and assumptions, the future events and trends discussed in this presentation may not occur and actual results could differ materially and adversely from those anticipated or implied in the forward-looking statements.

Although we believe that the expectations reflected in the forward-looking statements are reasonable, we cannot guarantee future results, levels of activity, performance, achievements or events and circumstances reflected in the forward-looking statements will occur. We are under no duty to update any of these forward-looking statements after the date of this presentation to conform these statements to actual results or revised expectations, except as required by law. You should, therefore, not rely on these forward-looking statements as representing our views as of any date subsequent to the date of this presentation. Moreover, except as required by law, neither we nor any other person assumes responsibility for the accuracy and completeness of the forward-looking statements contained in this presentation.

This presentation also contains estimates and other statistical data made by independent parties and by us relating to market size and growth and other data about our industry. This data involves a number of assumptions and limitations, and you are cautioned not to give undue weight to such estimates. Neither we nor any other person makes any representation as to the accuracy or completeness of such data or undertakes any obligation to update such data after the date of this presentation. In addition, projections, assumptions and estimates of our future performance and the future performance of the markets in which we operate are necessarily subject to a high degree of uncertainty and risk.

Confidential and Proprietary 2

Delivering Security Data & Analytics

that revolutionize the practice of cyber security

Differentiated Security Analytics 35% $35m

Technology Platform Now Strategic Imperative revenue CAGR quarterly billings

See End Notes for additional information and definitions Confidential and Proprietary 3

New Explosion Of High-Impact Cyber Attacks

IT CONTROL & VISIBILITY

vastly expanding attack surface

ATTACKER SOPHISTICATION & REACH

weaponization of cyber attacks

TIME

Confidential and Proprietary 4

Massive Shift to Risk-Based Approach to Security

NEW MODEL:

Risk-Based Security

OLD MODEL: SECURITY

Prevention-Based Security

DATA & ANALYTICS

“Block and Protect”

Growing Spend

By 2020,

60%

of enterprise information security budgets will be allocated for

Rapid Detection and Response Approaches

up from less than 10% in 2014.

- Gartner

Confidential and Proprietary 5

Rapid7 Solves Key Customer Questions …

Key

Customer AM I VULNERABLE? AM I COMPROMISED? AM I OPTIMIZED?

Questions:

THREAT INCIDENT SECURITY

EXPOSURE MANAGEMENT DETECTION & RESPONSE ADVISORY SERVICES

compliance SECURITY compliance SECURITY compliance SECURITY

reporting ANALYTICS reporting ANALYTICS reporting ANALYTICS

Legacy ATTACKER Log BEHAVIORAL Traditional SECURITY

Offerings Vulnerability INSIGHTS Aggregation ANALYTICS Testing ASSESSMENT

Management

REMEDIATION CONTEXT PROGRAM

Rapid7 STRATEGY

… with technology-based differentiation to provide security analytics-driven answers

Confidential and Proprietary 6

Technology Platform & Products

Confidential and Proprietary 7

Rapid7 Security Data & Analytics Technology Platform

Threat Exposure Incident Detection Security Advisory 3rd Party Apps

Management & Response Services

CONTEXT & ANALYTICS

User Behavior Exposure Attack Behavior

Analysis Analysis Analysis

DATA COLLECTION

Asset User Behavioral Mobile Cloud Controls 3rd Party

Info Data Data Info Activity Info Data

Rapid7 Data & Analytics Platform

extensive

DATA COLLECTION

… from the Endpoint to the Cloud

AGENTLESS

Architecture

PACKAGED ANALYTICS

Confidential and Proprietary 8

Rapid7’s Deep Security and Attacker Expertise

EXPERTISE

team of highly-skilled

Security Researchers

THREAT INTELLIGENCE research & attacker modeling

COMMUNITY EXPERTISE

Open Source Community

thousands of global users & contributors

near real-time

VISIBILITY

INTO NEW ATTACKS

Confidential and Proprietary 9

From Vulnerability to Threat Exposure Management

legacy compliance focus

Attack Remediation Simulation Analytics

Vulnerability IT

& Patch Workflow Reporting Integration

Vulnerability Threat Exposure

Management Management

Rapid7 Threat

Exposure Management:

Know your weak points Prioritize what matters Optimize remediation

RAPID7 TECHNOLOGY:

vulnerability management attack simulation web application assessment

Confidential and Proprietary 10

PRODUCT Nexpose EXAMPLE Rapid7’s Prioritized Risk Reduction

TRADITIONAL

VULNERABILITY MANAGEMENT

thousands of unintelligible alerts

ID Title Occurrences

MS05-43 Microsoft Windows DCOM RPCSS Service Vulnerabilities 14352

MS04-61 Microsoft Windows DCOM RPC Interface Buffer Overrun Vuln 11253

MS05-72 Microsoft Windows ASN.1 Library Integer Handling 2456

MS03-32 Windows TCP/IP Remote Code Execution 522

AP04-32 Apache Tomcat Directory Traversal 414

AW01-34 APR-util Library Integer Overflow 255

AP04-16 Apache 1.3 and 2.0 Web Server 116

FT01 ProFTPD 1.3 2xc2 and Prior_mod SQL Injection 98

VZ02 OpenVZ Multiple Vulnerabilities 64

HPJ01 HP NonStop Servers and Java 55

HW08 Huawei Multiple Device Bypass 32

MS04-47 Microsoft Messenger Service Buffer Overrun Vulnerability 28

RHL013 Red Hat Linux Instance 1.3 Multiple Vulnerabilities 28

PP32-1 Plug and Play Remote Access Vulnerability 19

SMOSL1 SQL_mod remote Once Single Access 18

Top 25 Remediations by Risk sd test June 25, 2015 01:59:24 GMT

Applying 25 Top Remediations Will Remediate 74% Vulnerabilities including:

66% published exploits 35% available malware kits

Affecting 1527 Assets

Remediations Remediated Vulns Affected Assets Risk

Configure SMB Signing for Windows 40 0 0 303 312800

Upgrade to the latest version of Atlassian JIRA 39 5 3 289 169730

clear, digestible & actionable by IT

Confidential and Proprietary 11

From Compliance Monitoring to Incident Detection & Response

legacy compliance

focus

Data

Integration

Contextual Mapping

Dynamic Behavioral Analysis

Data Silos Log Aggregation Static Rules

Traditional Security Monitoring Incident Detection & Response

RAPID7 Incident Response Services

TECHNOLOGY: detection & investigation

Confidential and Proprietary 12

PRODUCT EXAMPLE Rapid7’s Behavioral Analytics Advantage

UserInsight

COMPLIANCE DRIVEN SOLUTIONS

machine-based info and “alert overload”

WARNING: POTENTIAL BREACH

12,107 Incidents Detected

IP EVENT TIME

169.186.79.33 INTEL HIT (Targeted Indicator Match) 04:13:07

88.03.0.112 Possible ExFil 04:13:07

89.164.52.36 Trojan CRSS 04:14:52

29.165.14.15 INTEL HIT (Targeted Indicator Match) 04:16:22

25.24.00.02 INTEL HIT (Targeted Indicator Match) 04:19:43

26.14.25.78 Trojan CRSS 04:20:59

26.14.25.78 Trojan CRSS 04:21:06

26.14.25.78 Trojan CRSS 04:21:18

26.14.25.78 Trojan CRSS 04:21:19

26.14.25.78 Trojan CRSS 04:21:23

crisp & actionable user-based info

COMPROMISED USER:

Alex Vaughn

Director, Sales

Login from multiple countries

Login to multiple systems that user has never accessed previously

Exported data to AWS S3 storage

Confidential and Proprietary 13

Synergy & Leverage From Partner Ecosystem

Rapid7 has

more50 than

Platform Integrations with Partners

DATA

COLLABORATION

PARTNERS

Two-way data sharing ‘Single pane of glass’ Enhanced platform value

DATA WORKFLOW

PARTNERS

IT security integration Streamlines correction Improves IT efficiencies

DATA

INGESTION

PARTNERS

Enhances analytics

Enables detection

Simplifies

investigations

Confidential and Proprietary 14

Market & Customers

Confidential and Proprietary 15

Disrupting Spend and Expanding Our TAM

IDC

IT Security

SPEND AREAS

Security & Vulnerability Management $4.9

Network Intrusion Detection & Prevention 2.1

Endpoint Security Suites 2.3

Security Services 3.3

TOTAL MARKET TODAY $12.6B

See End Notes for additional information and definitions

RAPID7

Security Data & Analytics

OFFERINGS

Threat Exposure Management

Incident Detection & Response

Security Advisory Services

$12.6B

SECURITY

DATA &

ANALYTICS

market

opportunity

today

Confidential and Proprietary 16

Rapid7’s Winning Combination

Extensive Data Security & Collection Attacker Insights

Rapid7 Addresses Key Customer Pain Points With …

Contextual Intuitive Analytics User Experience

Confidential and Proprietary 17

Efficient & Engaged Go-to-Market Strategy

Threat Exposure Incident Detection Security Advisory Management & Response Services

RAPID7 GLOBAL SALES REACH

Inside Field Channel Sales Sales Partners

Up-sells

Cross-sells

Anywhere LAND …

EXPAND

Everywhere

Confidential and Proprietary 18

High-Quality, Rapidly Growing Customer Base

34% of the Fortune 1000

% +4,150 %

International Revenue 12 58 Enterprise Revenue

Security Data

& Analytics

Customers

Largest Industry % %

13 34 Customer Count Growth Segment (Technology)

See End Notes for additional information and definitions

Confidential and Proprietary 19

CUSTOMER Evolution From Traditional VM to TEM

CASE STUDY

One of the World’s Largest Software Companies

Rapid7 Solution

Saved ~40 hours of work per month with Nexpose dynamic asset groups and actionable remediation plans during proof of concept.

March 2014 July 2014

Land & Expand

2-Year Value = 5.6x Original Purchase Amount

Currently Own: 163k Nexpose IPs, Metasploit Pro and UserInsight

April 2015

Initial Purchase Additional Purchase

Nexpose Enterprise 120,000 Nexpose IPs 6,000 IPs Metasploit Pro Security Advisory Services

Additional Purchase

37,000 Additional Nexpose IPs Support Upgrades & Certifications UserInsight

Confidential and Proprietary 20

Multiple Drivers of Growth

1 2

5 3 4

1. Drive Analytics & Upgrade Enterprise

2. Continue to Grow Mid-market

3. Cross-sell Incident Detection & Response

with Increasing Customer Economics

4. Continue International Expansion

5. Serve as the Hub for Cyber Security

Confidential and Proprietary 21

Proven Leadership Team Driving Execution

Senior Management

Corey Thomas

President & CEO

Lee Weiner

SVP, Products & Engineering

Mike McKee

SVP, Services & Customer Success

HD Moore

Chief Research Officer

Steven Gatoff

Chief Financial Officer

Richard Moseley

SVP, Global Sales

Carol Meyers

Chief Marketing Officer

Nick Percoco

VP, Strategic Services

Board of Directors

Alan Matthews Mike Berry Ben Holzman Tim McAdam Ben Nye Jack Sweeney Chris Young

Co-founder CFO, Bain Capital Technology Bain Capital CEO, SVP, Head of

& Chairman Informatica Ventures Crossover Ventures Ventures SevOne Intel Security

Confidential and Proprietary 22

Financial Overview

Confidential and Proprietary 23

Q2 2015 Financial Highlights

1 Strong Revenue Growth of 44% YoY

2 High-Visibility Recurring & Ratable Revenue model with 61% Recurring Revenue and 83% of Q2 Revenue on Balance Sheet as of April 1, 2015

3 Strong continued Deferred Revenue Growth of 45% YoY

4 Solid Renewal Rate of 115% driving Attractive Customer Economics

5 Increasing Operating Efficiencies with material improvements in OpEx expense-to-revenue measures

See End Notes for additional information and definitions

Confidential and Proprietary 24

Strong Revenue Growth

35% CAGR

$77m $60m $46m $31m

2011 2012 2013 2014

+44% YoY +41% YoY $26m

$24m $18m $17m

Q1 2014 Q1 2015 Q2 2014 Q2 2015

Confidential and Proprietary 25

High Proportion of Recurring Revenue

81% of revenue

Products

Software

20% Content Subscription Managed Services Cloud-Based Subscription

Appliance

Maintenance

& Support

15% Maintenance & Support

19% of revenue

Professional Services

Professional Services

61% RECURRING REVENUE

See End Notes for additional information and definitions

Confidential and Proprietary 26

Strong Growth in Deferred Revenue and Visibility

+45% GROWTH (YOY)

$98m

$85m $89m

$67m $72m

$60m $61m

$46m $50m $53m

Q1 2013 Q2 2013 Q3 2013 Q4 2013 Q1 2014 Q2 2014 Q3 2014 Q4 2014 Q1 2015 Q2 2015

Current Deferred Long-Term Deferred

80%+

of quarterly revenue

already booked

entering quarter

each

Confidential and Proprietary 27

Compelling New Logo & Organic Customer Growth

New Sales Orders

44%

56% existing customers new customers

115%

renewal rate

See End Notes for additional information and definitions

LAND: EXPAND:

Initial Year Spend Up-sells + Cross-sells

2.4x

2011 2012 2013 2014

Initial Year Spend New Spend in Subsequent Years Renewals

Confidential and Proprietary 28

Strong and Diversified Revenue Profile

By Industry Vertical

Other Energy 4% 4%

Ed Tech

5% 13% Gov’t 8%

Financials 12% Comms 9%

Manufact. Healthcare 12% 11% Service Retail 11% 11%

See End Notes for additional information and definitions

By Customer Segment

42%

Mid-Market

58%

Enterprise

By Customer

No Single Customer e 2% of Revenue

By Geography

88% North America 12% Rest-of-World

Confidential and Proprietary 29

Investing for Growth & Achieving Operating Efficiencies

Marketing Sales &

(non-GAAP)

63% 64% 53% 55%

2013 2014 Q2 Q2 2014 2015

See End Notes for additional information and definitions

Development Research &

(non-GAAP)

35% 35% 33%

30%

2013 2014 Q2 Q2 2014 2015

Administrative General &

(non-GAAP)

19% 17% 16% 16%

2013 2014 Q2 Q2 2014 2015

Confidential and Proprietary 30

Favorable Operating Cash Flow Dynamics

(2%) (1%) (4%) (5%)

(13%)

(23%)

(26%) (28%)

(34%) (37%)

2012 2013 2014 Q2 2014 Q2 2015

Operating Cash Flow Margin Operating Income Margin (Non-GAAP)

See End Notes for additional information and definitions

greater Operating Cash Flow

up-front driven by customer payments

vs. longer-term ratable revenue recognition

& subscription model

Confidential and Proprietary 31

Investment Highlights

Disruptive

Security Data & Analytics Platform

Pioneering

IT Shift to Risk-Based Security

Strong

Recurring Revenue Growth & Visibility

Attractive

Customer Economics & Diverse Base

Compelling

And Growing Cyber Security Market

Confidential and Proprietary 32

End Notes

Page 3

$35m in quarterly billings is for Q2 2015 and derived from financial statements as Q2 2015 revenue of $26m + Q2 2015 deferred revenue balance of $98m – Q1 2015 deferred revenue balance of $89m.

35% revenue CAGR calculated on 2011-2014.

Page 16

Rapid7 estimates based on IDC data.

Page 19

All statistics are for Q2 2015 or as of June 30, 2015, as applicable.

Enterprise Revenue represents revenue from customers with greater than $1 billion in annual revenue or more than 2,500 employees as a percentage of total revenue.

Page 24

61% Recurring Revenue defined as revenue from Content Subscription, Managed Services, Cloud-Based Subscriptions, and Maintenance & Support for Q2 2015.

Represents renewal rate as of Q2 2015 and is calculated by dividing the dollar value of renewed customer agreements, including upsells and cross-sells of additional products, but excluding professional services, on a monthly basis in a trailing 12-month period by the dollar value of the corresponding expiring customer agreements, and then determining the average for the applicable period.

Page 26

20% Content Subscription and 15% Maintenance & Support arrangements represent the approximate percentage of software license list price per year.

81% Products and Maintenance & Support and 19% Professional Services metrics represents revenue from those two categories as a percentage of total revenue for Q2 2015.

61% Recurring Revenue defined as revenue from Content Subscription, Managed Services, Cloud-Based Subscriptions, and Maintenance & Support for Q2 2015.

Page 28

New Sales Orders and Renewal Rate information is for Q2 2015.

Page 29

All information presented is for Q2 2015.

Page 30

Operating expenses presented are on a non-GAAP basis and exclude stock-based compensation expense, amortization of intangible assets and acquisition related expenses.

Page 31

Operating cash flow margin represents operating cash flow as a percentage of total revenue.

Non-GAAP operating margin represents GAAP loss from operations, excluding stock-based compensation expense, amortization of intangible assets and acquisition related expenses as a percentage of total revenue.

Confidential and Proprietary 33

Rapid7, Inc.

100 Summer Street Boston, MA 02110

Confidential and Proprietary

EX-99.3

Exhibit 99.3

SECURITY

DATA &

ANALYTICS

Q2 2015 Financial Results

AUGUST 18, 2015 RAPID7 PROPRIETARY

Disclaimers

This presentation includes forward-looking statements. All statements contained in this presentation other than statements of historical facts, including statements regarding future results of operations and the financial position of Rapid7, Inc. (“Rapid7,” “we,” “us” or “our”) our business strategy and plans and our objectives for future operations, are forward-looking statements. The words “anticipate,” believe,” “continue,” “estimate,” “expect,” “intend,” “may,” “will” and similar expressions are intended to identify forward-looking statements. We have based these forward-looking statements largely on our current expectations and projections about future events and financial trends that we believe may affect our financial condition, results of operations, business strategy, short-term and long-term business operations and objectives, and financial needs. These forward-looking statements are subject to a number of risks and uncertainties, including, without limitation, those set forth in the “Risk Factors” section of our prospectus filed pursuant to Rule 424(b)(4) under the Securities Act of 1933, as amended, on July 17, 2015. Moreover, we operate in a very competitive and rapidly changing environment. New risks emerge from time to time. It is not possible for our management to predict all risks, nor can we assess the impact of all factors on our business or the extent to which any factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements we may make. In light of these risks, uncertainties and assumptions, the future events and trends discussed in this presentation may not occur and actual results could differ materially and adversely from those anticipated or implied in the forward-looking statements.

Although we believe that the expectations reflected in the forward-looking statements are reasonable, we cannot guarantee future results, levels of activity, performance, achievements or events and circumstances reflected in the forward-looking statements will occur. We are under no duty to update any of these forward-looking statements after the date of this presentation to conform these statements to actual results or revised expectations, except as required by law. You should, therefore, not rely on these forward-looking statements as representing our views as of any date subsequent to the date of this presentation. Moreover, except as required by law, neither we nor any other person assumes responsibility for the accuracy and completeness of the forward-looking statements contained in this presentation.

This presentation also contains estimates and other statistical data made by independent parties and by us relating to market size and growth and other data about our industry. This data involves a number of assumptions and limitations, and you are cautioned not to give undue weight to such estimates. Neither we nor any other person makes any representation as to the accuracy or completeness of such data or undertakes any obligation to update such data after the date of this presentation. In addition, projections, assumptions and estimates of our future performance and the future performance of the markets in which we operate are necessarily subject to a high degree of uncertainty and risk.

Rapid7 Proprietary 2

Q2 2015 Financial Highlights

1 Strong Revenue Growth of 44% YoY

2 High-Visibility Recurring & Ratable Revenue model with 61% Recurring

Revenue and 83% of Q2 Revenue on Balance Sheet as of April 1, 2015

3 Strong continued Deferred Revenue Growth of 45% YoY

4 Solid Renewal Rate of 115% driving Attractive Customer Economics

5 Increasing Operating Efficiencies with material improvements in OpEx

expense-to-revenue measures

See End Notes for additional information and definitions

Rapid7 Proprietary 3

Q2 2015 Summary Selected Financial Results

$ %

(amounts in millions, except per share data) Q2 2015 Q2 2014 Change Change

Revenue:

Products $14.6 $11.0 $3.6 33% Maintenance & support 6.3 4.5 1.8 40% Professional services 4.9 2.4 2.5 105%

Total Revenue $25.8 $17.9 $7.9 44%

Loss from operations (GAAP) $(8.6) $(7.4) $(1.2) (16%) Loss from operations (non-GAAP)1 $(7.1) $(6.5) $(0.6) (9%) Net loss (GAAP) $(9.2) $(8.2) $(1.0) (13%) Net loss (non-GAAP)1 $(7.8) $(7.3) $(0.5) (6%) Net loss per share (GAAP) $(2.59) $(1.85) $(0.74) (40%) Net loss per share (non-GAAP)1 $(0.61) $(0.58) $(0.03) (5%) Weighted-average common shares outstanding 12.7 12.8

Pro forma Net loss per share $(0.60) Pro forma weighted-average common shares 38.8

Operating cash flow $(1.2) $(2.3) $1.1 46% Deferred revenue at period-end $97.5 $67.4 $30.1 45%

1The Company defines non-GAAP loss from operations and non-GAAP net loss as GAAP loss from operations and GAAP net loss excluding stock-based compensation expense, amortization of intangible assets and acquisition related expenses. See End Notes for definitions and reconciliation of GAAP to non-GAAP metrics.

Rapid7 Proprietary 4

Strong Revenue Growth

+44% YoY

+41% YoY $26m

35% CAGR

$77m $24m

$18m

$60m

$17m

$46m

$31m

2011 2012 2013 2014 Q1 2014 Q1 2015 Q2 2014 Q2 2015

Rapid7 Proprietary 5

High Proportion of Recurring Revenue

81% of revenue 19% of revenue

Maintenance Professional

Products

& Support Services

Software 15% Maintenance & Support Professional Services

20% Content Subscription

Managed Services

Cloud-Based Subscription

Appliance

61% RECURRING REVENUE

See End Notes for additional information and definitions

Rapid7 Proprietary 6

Strong Growth in Deferred Revenue and Visibility

+45% GROWTH (YOY) 83%

$98m

$89m

$85m of Q2 2015

$72m revenue

$67m

$60m $61m already

$50m $53m

$46m booked

entering the quarter

Q1 2013 Q2 2013 Q3 2013 Q4 2013 Q1 2014 Q2 2014 Q3 2014 Q4 2014 Q1 2015 Q2 2015

Current Deferred Long-Term Deferred

See End Notes for additional information and definitions

Rapid7 Proprietary 7

Q2 2015 Revenue Flow Driving Strong Visibility

Q2 2015 billings

88%

12%

$30.4m Recorded as deferred revenue and ton be recognized in future periods.

$4.3 m Converts to revenue and is recognized as revenue in the current quarter

Q2 2015 REVENUE $4.3M 17% 83% $25.8M

$21.5m Recognized as revenue from deferred revenue (frpm prior period billings)

June 30, 2015 Balance Sheet

Deferred Revenue

March 31, 2015 Balance Sheet

Deferred Revenue

as of March 31

See End Notes for additional information and definitions

Rapid7 Proprietary 8

Continued Improvement in Gross Margins

95% 86% 86% 87%

85% 76%

72% 74%

75% improvements in

65% Q2 2015

55% Gross Margin

45%

35% driven by

25% 19% investments made in

15% 2H 2014

15% 9%

and early 2015

5%

Q2 2014 Q1 2015 Q2 2015

Product and Maintenance & Support Professional Services Total Gross Margin

See End Notes for additional information and definitions

Rapid7 Proprietary 9

Favorable Operating Cash Flow Dynamics

greater Operating

(2%) (1%)

(4%) (5%) Cash Flow

(13%)

driven by

(23%) (37%) up-front

(26%) (28%) customer

(34%)

payments

2012 2013 2014 Q1 2015 Q2 2015 vs.

longer-term

ratable

Operating Cash Flow Margin Operating Income Margin (Non-GAAP) revenue recognition

& subscription model

See End Notes for additional information and definitions

Rapid7 Proprietary 10

High-Quality, Rapidly Growing Customer Base

34% of the Fortune 1000

% +4,150 %

International Revenue 12 58 Enterprise Revenue

Security Data

& Analytics

Customers

Largest Industry % %

13 34 Customer Count Growth

Segment (Technology)

See End Notes for additional information and definitions

Rapid7 Proprietary 11

Continued Improvements in Renewal Rates

140%

Increase in

120% 115%

111% 112%

109% Renewal Rates

100% driven from a combination of

87% renewals, up-sells and cross sells

83% 85% 85%

driving better customer economics.

80%

and

60% Increase in

Expiring Revenue

40% Renewal Rates

20%

. with core Enterprise customer renewals

coming in at more than 90% for Q2.

0%

Renewal Rate Expiring Renewal Rate

2013 2014 Q1 2015 Q2 2015

See End Notes for additional information and definitions

Rapid7 Proprietary 12

Q2 2015 Summary Financial Statements

Balance Sheet

June 30, 2015

($ in millions) June 30, 2015 Pro Forma

Assets

Cash and Cash Equivalents $27.0 $140.9

Accounts Receivable, Net 26.4 26.4

Prepaid Expenses & Other Current Assets 6.3 4.2

Total Current Assets $59.7 $171.5

Property and Equipment, Net 7.6 7.6

Goodwill and Intangible Assets 18.5 18.5

Other Assets 0.7 0.7

Total Assets $86.5 $198.3

Liabilities & Stockholders’ Equity

Current Liabilities $16.8 $16.1

Total Deferred Revenue 97.5 97.5

Total Term Loan 17.1 17.1

Other Long-Term Liabilities 5.1 5.1

Total Liabilities $136.5 $135.8

Redeemable Convertible Preferred Stock 246.7 -

Total Stockholders’ Deficit (296.7) 62.5

Total Liabilities & Stockholders’ Equity $86.5 $198.3

See End Notes for additional information and definitions

Rapid7 Proprietary 13

Guidance | Q3 and Full-Year 2015

Rapid7 anticipates total revenue, non-GAAP loss from operations, and non-GAAP

loss per share to be in the following ranges for Q3 and Full-Year 2015:

Q3 2015 FULL-YEAR 2015

Total Revenue $25.4 to $26.8 million $102 to $105 million

Loss From Operations (non-GAAP)1 ($10.9) to ($9.9) million ($35.4) to ($33.4) million

Net Loss Per Share (non-GAAP)1 ($0.38) to ($0.35) ($1.56) to ($1.48)

Weighted average common stock outstanding 33.0 million 24.6 million

Guidance for the third quarter and full-year 2015 does not include any potential impact of any foreign exchange gains or losses.

1 Non-GAAP guidance excludes estimates for stock-based compensation expense, amortization of intangible assets and acquisition related expenses. A reconciliation of

non-GAAP guidance measures to the most comparable GAAP measures is not available on a forward-looking basis. Rapid7 has provided a reconciliation of historical non-

GAAP financial measures to the most comparable GAAP measures in the financial statement tables included in End Notes of this presentation.

Rapid7 Proprietary 14

End Notes

Page 3

61% Recurring Revenue defined as revenue from Content Subscription, Managed Services, Cloud-Based Subscriptions, and Maintenance & Support for Q2 2015.

Represents renewal rate as of Q2 2015 and is calculated by dividing the dollar value of renewed customer agreements, including upsells and cross-sells of additional products, but excluding professional services, on a monthly basis in a trailing 12-month period by the dollar value of the corresponding expiring customer agreements, and then determining the average for the applicable period.

Page 4

The unaudited pro forma net loss per share for the three and six months ended June 30, 2015 has been provided to reflect the pro forma effect of the Company’s IPO, which occurred in July 2015, and assumes the following: (i) the conversion of all outstanding shares of the Company’s redeemable convertible preferred stock into an aggregate of 18,322,605 shares of common stock as of the beginning of the period and (ii) the sale and issuance of 7,730,000 shares of common stock as of the beginning of the period. The amount recorded to reflect the beneficial conversion charge of $14.2 million associated with the conversion of the Company’s Series D preferred stock into common stock has been included and the amounts recorded to reflect the accretion of redeemable convertible preferred stock to redemption value has been added back to arrive at pro form net loss attributable to common stockholders.

Page 6

20% Content Subscription and 15% Maintenance & Support arrangements represent the approximate percentage of software license list price per year.

81% Products and Maintenance & Support and 19% Professional Services metrics represents revenue from those two categories as a percentage of total revenue for Q2 2015.

61% Recurring Revenue defined as revenue from Content Subscription, Managed Services, Cloud-Based Subscription and Maintenance & Support.

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$34.7m in billings is for Q2 2015 and derived from financial statements as Q2 2015 revenue of $25.8m + Q2 2015 deferred revenue balance of $97.5m – Q1 2015 deferred revenue balance of $88.6m.

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Margins calculated as a % of revenue.

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Margins calculated as a percentage of revenue.

Non-GAAP operating income represents the GAAP loss from operations, excluding stock-based compensation expense, amortization of intangible assets and acquisition related expenses.

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All statistics are for Q2 2015 or as of June 30, 2015, as applicable.

Enterprise customers represent customers with greater than $1 billion in annual revenue or greater than 2,500 employees.

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Renewal rate is calculated by dividing the dollar value of renewed customer agreements, including upsells and cross-sells of additional products, but excluding professional services, on a monthly basis in a trailing 12-month period by the dollar value of the corresponding expiring customer agreements, and then determining the average for the applicable period.

Expiring renewal rate is calculated similar to the renewal rate however does not take into account any upsells or cross-sells.

Enterprise Revenue represents revenue from customers with greater than $1 billion in annual revenue or greater than 2,500 employees as a percentage of total revenue.

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Current liabilities represents accounts payable, accrued expense and other current liabilities.

Total deferred revenue represents both current and non-current portions of deferred revenue.

Total term loan represents both current and non-current portions of term loan.

The unaudited pro forma balance sheet as of June 30, 2015 has been provided to reflect the pro forma effect of Rapid7, Inc.’s (the “Company”) initial public offering (the “IPO”), which occurred in July 2015, and assumes the following: (i) the conversion of the Company’s redeemable convertible preferred stock into common stock and related beneficial conversion charge of $14.2 million associated with the conversion of the Series D preferred stock into common stock, (ii) net proceeds from the IPO of $107.4 million after deducting the underwriting discount and estimated offering expenses, and (iii) net proceeds from the private placement issuance of $5.0 million that occurred concurrently with the IPO.

Rapid7 Proprietary 15

End Notes | GAAP to Non-GAAP Reconciliations

GAAP to non-GAAP Reconciliation

(in thousands, except per share data)

Q2 2015 Q2 2014

Total gross profit (GAAP) $19,063 $13,670

Plus: Stock-based compensation expense 52 47

Plus: Amortization of intangible assets 276 217

Total gross profit (non-GAAP) $19,391 $13,934

Gross margin % (non-GAAP) 75% 78%

Loss from operations (GAAP) $(8,573) $(7,393)

Plus: Stock-based compensation expense 831 631

Plus: Amortization of intangible assets 276 217

Plus: Acquisition related expenses 360 —

Loss from operations (non-GAAP) $(7,106) $(6,545)

Net loss attributable to common stockholders (GAAP) $(33,032) $(23,651)

Plus: Accretion of preferred stock to redemption value 23,788 15,464

Net loss (GAAP) (9,244) (8,187)

Plus: Stock-based compensation expense 831 631

Plus: Amortization of intangible assets 276 217

Plus: Acquisition related expenses 360 —

Net loss (non-GAAP) $(7,777) $(7,339)

Net loss per share, basic and diluted (non-GAAP) $(0.61) $(0.58)

Weighted average shares used in GAAP and non-GAAP net

loss per share, basic and diluted 12,745 12,763

Rapid7 Proprietary 16

Rapid7, Inc.

100 Summer Street

Boston, MA 02110

Rapid7 Proprietary