Rapid7, Inc. - StifelRapid7, Inc. Common Stock We are offering 1,500,000 shares of our common stock, and the selling stockholders identified in this prospectus supplement, including

424B5 1 d529415d424b5.htm 424B5

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Filed pursuant to Rule 424(b)(5) Registration No. 333-218189

PROSPECTUS SUPPLEMENT (To Prospectus dated June 2, 2017)

5,180,000 Shares

Rapid7, Inc. Common Stock

We are offering 1,500,000 shares of our common stock, and the selling stockholders identified in this prospectus supplement, including our Chief Executive Officer and the Chairman of our Board of Directors, are offering an aggregate of 3,680,000 shares of our common stock pursuant to this prospectus supplement and the accompanying prospectus. We will not receive any proceeds from the sale of shares of common stock by the selling stockholders.

Our common stock is listed on The Nasdaq Global Market under the symbol “RPD.” On January 25, 2018, the last reported sale price for our common stock on The Nasdaq Global Market was $22.87 per share.

We are an “emerging growth company” as defined under the U.S. federal securities laws and have elected to comply with certain reduced public company disclosure and reporting requirements. See “Prospectus Summary—Implications of Being an Emerging Growth Company.”

Investing in our common stock involves a high degree of risk. See “Risk Factors” beginning on page S-10 of this prospectus supplement, beginning on page 5 of the accompanying prospectus and in the documents incorporated by reference into this prospectus supplement.

Per Share Total

Public offering price $ 22.00 $113,960,000Underwriting discounts and commissions $ 0.99 $ 5,128,200Proceeds to Rapid7 (before expenses) $ 21.01 $ 31,515,000Proceeds to selling stockholders (before expenses) $ 21.01 $ 77,316,800

(1) See “Underwriting” beginning on page S-22 for a description of the compensation payable to the underwriters.

The underwriters have an option to purchase a maximum of 770,000 additional shares of common stock from certain of the selling stockholders at the public offering price, less underwriting discounts and commissions, within 30 days from the date of this prospectus supplement. See “Underwriting” for more information.

(1)

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1/30/2018https://www.sec.gov/Archives/edgar/data/1560327/000119312518021695/d529415d424b5...

Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of these securities or determined if this prospectus supplement or the accompanying prospectus is truthful or complete. Any representation to the contrary is a criminal offense.

We expect that delivery of the shares of common stock will be made to investors in book-entry form through The Depository Trust Company on or about January 30, 2018.

Barclays RBC Capital Markets

KeyBanc Capital Markets StifelCowen Raymond James William Blair BTIG

Prospectus Supplement dated January 25, 2018

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TABLE OF CONTENTS

Prospectus Supplement

About this Prospectus Supplement S-ii

Prospectus Supplement Summary S-1

Risk Factors S-10

Special Note Regarding Forward-Looking Statements S-11

Use of Proceeds S-12

Price Range of Common Stock S-13

Dividend Policy S-13

Capitalization S-14

Dilution S-15

Selling Stockholders S-16

Material U.S. Federal Income Tax Considerations for Non-U.S. Holders S-18

Underwriting S-22

Legal Matters S-29

Experts S-29

Where You Can Find More Information S-29

Incorporation of Certain Information by Reference S-29

Prospectus

About this Prospectus 1

Prospectus Summary 2

Risk Factors 5

Special Note Regarding Forward-Looking Statements 5

Use of Proceeds 5

Description of Capital Stock 6

Selling Stockholders 11

Plan of Distribution 12

Legal Matters 15

Experts 15

Where You Can Find More Information 15

Incorporation of Certain Information by Reference 15

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ABOUT THIS PROSPECTUS SUPPLEMENT

This prospectus supplement and the accompanying prospectus are part of a registration statement that we filed with

the Securities and Exchange Commission, or SEC, using a shelf registration process. Both this prospectus supplement and

the accompanying prospectus include or incorporate by reference important information about us, our common stock and

other information you should know before investing. You should read both this prospectus supplement and the

accompanying prospectus and the documents incorporated herein and therein by reference (see the sections entitled

“Incorporation of Certain Information by Reference”), as well as any additional information described under “Where You

Can Find More Information” in this prospectus supplement before making an investment decision.

We and the selling stockholders have not, and the underwriters have not, authorized anyone to provide any

information other than that contained or incorporated by reference in this prospectus supplement, in the accompanying

prospectus or in any free writing prospectus that we have authorized for use in connection with this offering. Neither we

nor the selling stockholders, nor the underwriters, take responsibility for, and can provide no assurance as to the reliability

of, any other information that others may give you. This prospectus supplement and the accompanying prospectus do not

constitute an offer to sell or the solicitation of an offer to buy any securities other than the securities described in this

prospectus supplement or an offer to sell or the solicitation of any offer to buy such securities in any circumstances in

which such offer or solicitation is unlawful. You should assume that the information appearing in this prospectus

supplement and the accompanying prospectus, the documents incorporated by reference into this prospectus supplement

and the accompanying prospectus, and in any related free writing prospectus that we have authorized for use in connection

with this offering, is accurate only as of their respective dates. Our business, financial condition, results of operations and

prospects may have changed materially since those dates.

This prospectus supplement may add to, update or change the information in the accompanying prospectus. To the

extent there is a conflict between the information contained in this prospectus supplement, on the one hand, and the

information contained in the accompanying prospectus or in any document incorporated by reference that was filed with

the SEC before the date of this prospectus supplement, on the other hand, you should rely on the information in this

prospectus supplement. If any statement in one of these documents is inconsistent with a statement in another document

having a later date, the statement in the document having the later date modifies or supersedes the earlier statement.

Unless the context otherwise indicates, references in this prospectus supplement and accompanying prospectus to

“Rapid7,” “we,” “our,” “us” and “the Company” refer, collectively, to Rapid7, Inc., a Delaware corporation, and its

subsidiaries on a consolidated basis. Our principal executive offices are located at 100 Summer Street, Boston,

Massachusetts 02110 and our telephone number is (617) 247-1717.

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PROSPECTUS SUPPLEMENT SUMMARY

The following summary highlights selected information contained or incorporated by reference elsewhere in this

prospectus supplement and does not contain all of the information that you should consider in making your investment

decision. Before investing in our common stock, you should carefully read this entire prospectus supplement, the

accompanying prospectus and any related free writing prospectus that we have authorized for use in connection with

this offering, including the information under the caption “Risk Factors” herein and therein and under similar

headings in the documents that are incorporated by reference herein or therein. You should also carefully read the

other information incorporated by reference into this prospectus supplement, including our consolidated financial

statements and the related notes, and the exhibits to the registration statement of which this prospectus supplement

and the accompanying prospectus is a part.

Rapid7, Inc.

Business Overview

Organizations of all sizes are faced with a more sophisticated and motivated set of cyber attackers. Coupled with

an increasingly complex IT environment and expanding attack surface, driven by mobility and a shift to the cloud,

security and IT teams are struggling to maintain adequate levels of cyber security, provide visibility to their

management teams, and meet increasing regulatory requirements. At the same time, they must navigate a shortage of

capable cyber security professionals. Out of these challenges, the concept of Security Operations, or SecOps, is

emerging. SecOps is a movement that recognizes that Security and IT Operations must work together to deliver better

security and more nimbly adapt to emerging threats, without adding significant resources. SecOps requires solutions

that provide visibility, analytics and automation that enable IT, Security and DevOps to work together to achieve

significantly higher levels of productivity and success.

Rapid7 is a leading provider of security and IT analytics and automation solutions for SecOps, and is trusted by

professionals around the world to provide visibility, analytics and automation to help manage risk, simplify IT

complexity and drive innovation. Our solutions, which include vulnerability management, incident detection and

response, security information and event management, or SIEM, application security testing, log analytics, and

security orchestration and automation all focus on the critical needs of enterprises for greater visibility into their

environments, analytics that provide context to complex data, and automation that enables SecOps teams to scale and

more efficiently to address critical security and IT tasks.

We combine our extensive experience in collecting data from an ever-expanding IT environment, our deep

insight into attacker behaviors and techniques, and our powerful and proprietary analytics to provide solutions that can

quickly and efficiently identify and prioritize risks and active threats in an enterprise’s IT environment. Our broad

data collection capabilities encompass endpoints, servers, applications, users, cloud-based assets, client devices,

network activity, log data and information from third-party applications. We also provide workflows and automations

that can enable and accelerate remediation of these risks and active threats. We have designed our solutions to be easy

to deploy and use for security and IT teams of all sizes.

We offer analytic solutions across three core areas. Our Vulnerability Management offerings include our

industry-leading vulnerability management, web application security testing and attack simulation products. These

solutions provide enterprises with comprehensive, yet prioritized, visibility into potential cyber risks across their IT

environment. We have also added remediation workflows to help ensure that these risks can be easily mitigated. Our

Incident Detection and Response solutions are designed to enable organizations to rapidly detect and respond to cyber

security incidents and breaches across physical, virtual and cloud assets, including those posed by the behaviors of

their users. These solutions combine the collection of massive amounts of data with our core analytics and machine-

learning-driven user behavioral analytics to simplify the task of identifying

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and responding to potential breaches. Our IT Analytics and Automation solutions are designed to allow operations teams to quickly gain visibility into their IT environment and facilitate automated workflows to eliminate repetitive, manual and labor-intensive tasks. Finally, to complement our SecOps products, we offer a range of services, including managed services based on our software solutions, incident response services, security advisory services, and deployment and training.

As of December 31, 2017, we had more than 7,000 customers, including 52% of the Fortune 100. We have experienced strong revenue growth, with revenue increasing from $46.0 million in 2012 to $157.4 million in 2016, representing a 36% compound annual growth rate. In the third quarter of 2017, 71% of our revenues were recurring revenues. We incurred net losses of $49.9 million, $49.0 million and $32.5 million in 2015, 2016 and the nine months ended September 30, 2017, respectively, as we continued to invest for long-term growth.

Our Analytics and Automation Cloud

The Rapid7 Insight Platform is at the core of our security and IT analytics product offerings. The platform was built in the cloud using our extensive experience in collecting and analyzing data to enable our customers to create and manage active, analytics-driven cyber security and IT operations management programs. Our robust data collection architecture supports gathering a wide swath of organizational and environmental data from endpoints to the cloud, including key data about user-specific behavior. By utilizing our powerful, proprietary analytics to assess and understand the context and relationships around users, IT assets and cyber threats within a customer’s environment, our solutions can provide our customers with specific, actionable insights critical for their SecOps approach. We designed the Rapid7 Insight Platform to allow customers to collect their data once and leverage that same data across multiple solutions, providing shared visibility across teams, improved and automated workflows, and reducing time to value for additional solutions. The design and development of our Insight Platform includes the following key features and benefits:

Holistic Dataset for Managing IT Operations and Cyber Security. Our Insight Platform collects information from across an organization’s environment into a unified dataset. Our platform also applies context to events, including user and asset level details. We overlay this against our comprehensive and continuously expanding set of known vulnerabilities, exploits and threat intelligence, providing SecOps professionals a holistic view of their IT environment.

Agentless and Agent-Based Architecture. We developed our platform with flexible processing technologies that employ both agentless data collection and our own internally-developed endpoint agent technology, which

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enables rapid and seamless integration of our products into our customers’ IT environments and provides IT professionals with instant visibility into their dynamic and rapidly-expanding IT ecosystem. This means it is much easier to deploy our Insight agent, potentially increasing the time to value for not just one of our products, but many of them.

Fast Search. Our search technology enables IT and security professionals to search across their entire IT environment including endpoints and, unlike other machine search solutions, provides live access without having to wait for lengthy indexing processes. These capabilities, along with real time and easily accessible search across raw logs and endpoints for known patterns with intuitive search queries, can enable IT security professionals to access their data for operational purposes.

User Behavior Analytics. Our Insight Platform creates a behavior profile for each user in a customer’s IT environment and correlates every event with a user, asset or application. User behavior profiles can then be automatically analyzed to identify suspicious user behavior and compromised user credentials. Our ability to provide rapid context around users and assets involved in an incident can significantly reduce investigation time, enabling organizations to more quickly respond to, contain and mitigate breaches.

Live Dashboards, Remediation Workflows and Automation. Our Insight Platform includes live dashboards which provide customers real-time, dynamic visibility into their risks, potential threats and progress to remediation all based on a shared reporting and visualization service. Remediation workflows enable customers to initiate, manage, prioritize and monitor the progress of vulnerability remediation. We also provide the ability to create automated workflows that can accelerate incident detection, response, and resolution.

Robust Platform and Customer Data Security. Our Insight Platform was designed to provide a secure environment for both our data and that of our customers. We deploy a variety of technologies and industry-leading practices such as physical and logical customer data segregation, network segmentation, audited and monitored access level controls, data anonymization, encryption and separated development-staging-production environments to help ensure that the data collected from a customer’s environment remains proprietary and secure. We have achieved Service Organization Control, or SOC, II Type 2 certification for the foundation of our platform and are continuing to expand the specific compliance regimes for which we are audited.

Enterprise-Grade Scalability. Our Insight Platform provides a high level of horizontal scalability. We leverage on-premise deployment models and Amazon Web Services, or AWS, to achieve a high degree of redundancy, fault tolerance and cost-effective operations. Our automated deployment technologies enable us to add new AWS instances or additional services rapidly. Our infrastructure architecture is designed to process large amounts of data and easily incorporate new data sources, including on premise, cloud and mobile. Our platform is designed to support customers with large numbers of users or with geographically dispersed environments, and we have scaled to meet the needs of customers with over 2.5 million active assets and 700,000 active users as of December 31, 2017.

Extensible Modern Platform. Our Insight Platform provides a rich set of application program interfaces, or APIs, and services that enable customers, partners and developers to import and export data and utilize our analytics capabilities. This allows us to easily integrate with other security tools in the customer’s environment and also enables customers to build bespoke applications and analysis on top of the data that we gather.

Our Market Opportunity

Our estimate, based on International Data Corporation, or IDC, data, is that the overall market for IT and security analytics and automation solutions was a $6.9 billion opportunity in 2017. Included in our estimates are all or a portion of the markets for Vulnerability Assessment, Policy and Compliance, Security Information and Event Management, Forensics and Incident Management, IT Operations Analytics-Public Cloud, IT Automation

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and Configuration Management Software and IT Operations Management Software. As our solutions expand to address more of the SecOps opportunity, we believe we may be able to address portions of the broader IT Operations Management Software market, as well as the IT Automation and Configuration Management Software market, which would expand our estimated overall market opportunity in 2017 to $22.2 billion, based on IDC data.

Recent Developments

This recent developments section includes forward-looking statements. All statements contained herein other than

statements of historical facts, including, without limitation, statements regarding our expectations regarding our

financial and operating results for the year and three months ended December 31, 2017 and our future financial and

business performance, 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, risk related to the timing of our recognition of deferred revenue, 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. For additional information regarding the

various risks and uncertainties inherent in estimates of this type, see “Special Note Regarding Forward-Looking

Statements” elsewhere in this prospectus supplement.

Preliminary Financial Results

The following preliminary financial information for the three months and the year ended December 31, 2017 is

based upon our estimates and subject to completion of our financial closing procedures. Moreover, these data have

been prepared solely on the basis of currently available information by, and are the responsibility of, Rapid7. Our

independent registered public accounting firm, KPMG LLP, has not audited or reviewed, and does not express an

opinion with respect to, these data. This summary is not a comprehensive statement of our financial results for this

period, and our actual results may differ materially from these estimates due to the completion of our financial closing

procedures, final adjustments, completion of the audit of our financial statements and other developments that may

arise between now and the time the audit of our financial statements is completed. Our actual results for the three

months and the year ended December 31, 2017 will not be available until after this offering is completed. There can

be no assurance that these estimates will be realized, and estimates are subject to risks and uncertainties, many of

which are not within our control.

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We have prepared estimates of the following preliminary financial data for the three months and the year ended December 31, 2017.

Year ended

December 31, 2017 % Change

(year-over-year)

Three months ended

December 31, 2017 % Change

(year-over-year)Range Range

Low High Low High Low High Low High

(dollars in millions)

GAAP Data

Revenue $200.4 $200.7 27% 27% $ 57.2 $ 57.5 27% 28% Loss from operations $ (49.3) $ (49.0) $ (13.9) $ (13.6) Net loss $ (46.5) $ (45.8) $ (14.0) $ (13.3) Cash flows from operating

activities $ 12.5 $ 13.0

Other Data

Calculated billings(1) $254.8 $255.8 30% 30% $ 92.0 $ 93.0 42% 43% Annualized recurring revenue(2) $163.0 $164.0 34% 35% $ 163.0 $ 164.0 34% 35% Non-GAAP loss from operations

(3) $ (26.5) $ (26.3) $ (7.9) $ (7.7)

(1) Calculated billings is a non-GAAP measure that we define as total revenue recognized in accordance with generally accepted accounting principles, or GAAP, plus the change in deferred revenue from the beginning to the end of the period. We consider calculated billings to be a useful metric for management and investors, as a supplement to the corresponding GAAP measure of total revenue, because billings drive deferred revenue, which is an important indicator of the health and visibility of trends in our business, and represents a significant percentage of future revenue. We regularly monitor calculated billings because we believe the measure offers information regarding the performance of our business. With the expansion of our subscription, cloud-based product offerings (InsightVM, InsightIDR, InsightAppSec, and InsightOps) on the Insight platform, we may realize a shortening of our average contract duration, which should be taken into consideration when evaluating calculated billings. Our use of calculated billings has limitations as an analytical tool and should not be considered in isolation or as a substitute for revenue recognition or revenue measurement, or an analysis of our results as reported under GAAP. Also, it is important to note that other companies, including companies in our industry, may not use calculated billings, may compute billings differently, may have different billing frequencies, or may use other financial measures to evaluate their performance, all of which could reduce the usefulness of calculated billings as a comparative measure. The following table presents a reconciliation of calculated billings to revenue, the most directly comparable GAAP measure, for each of the periods indicated:

Year ended

December 31, 2017

Three months ended

December 31, 2017

Range Range

Low High Low High

(in millions)

Revenue $200.4 $200.7 $ 57.2 $ 57.5Deferred revenue, end of period 223.4 224.1 223.4 224.1Deferred revenue, beginning of period 169.1 169.1 188.6 188.6

Calculated billings $254.8 $255.8 $ 92.0 $ 93.0

(2) Annualized recurring revenue is defined as the annual value of all recurring revenue related to contracts in place at the end of the period.

(3) Non-GAAP loss from operations is a non-GAAP measure that we define as loss from operations calculated in accordance with GAAP plus stock-based compensation expense, amortization of acquired intangible assets and acquisition-related expense. We consider non-GAAP loss from operations to be a useful metric for management and investors, as a supplement to the corresponding GAAP measure of loss from

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operations, because non-GAAP loss from operations excludes non-cash charges that we do not believe to be indicative of our core operating results. We regularly monitor non-GAAP loss from operations because we believe the measure offers valuable information regarding the performance of our business and will help investors better understand our operating performance on a period-to-period basis. Our use of non-GAAP loss from operations has limitations as an analytical tool and should not be considered in isolation or as a substitute for an analysis of our results as reported under GAAP. Also, it is important to note that other companies, including companies in our industry, may not use non-GAAP loss from operations, may compute non-GAAP loss from operations differently or may use other financial measures to evaluate their performance, all of which could reduce the usefulness of non-GAAP loss from operations as a comparative measure. The following table presents a reconciliation of non-GAAP loss from operations to loss from operations calculated in accordance with GAAP, the most directly comparable GAAP measure, for each of the periods indicated:

Year ended

December 31, 2017

Three months ended

December 31, 2017

Range Range

Low High Low High

(in millions)

Loss from operations (GAAP) $(49.3) $(49.0) $ (13.9) $ (13.6) Stock-based compensation expense 19.7 19.6 5.0 4.9Amortization of acquired intangible assets 2.9 2.9 1.0 1.0Acquisition-related expense 0.2 0.2 — —

Non-GAAP loss from operations $(26.5) $(26.3) $ (7.9) $ (7.7)

Below we have provided information regarding comparisons to prior year and quarters for context.

Revenue

The increase in revenue for the year and three months ended December 31, 2017 was driven by increased adoption across our solutions globally.

GAAP and non-GAAP loss from operations

Our loss from operations on both a GAAP and non-GAAP basis for the year ended December 31, 2017 reflected our revenue growth, partially offset by increased costs of goods sold and increased sales and marketing expense. Our loss from operations on both a GAAP and non-GAAP basis for the three months ended December 31, 2017, reflected our revenue growth, partially offset by increased costs of goods sold and increased commissions as a result of our increased calculated billings.

Net loss

Our net loss for the year ended December 31, 2017 reflected our revenue growth, partially offset by increased costs of goods sold and increased sales and marketing expense. Our net loss for the three months ended December 31, 2017, reflected our revenue growth, partially offset by increased costs of goods sold and increased commissions as a result of our increased calculated billings.

Cash flow from operating activities

Our increased cash flow from operating activities for the year ended December 31, 2017 was driven by increased collections as a result of our increased calculated billings, partially offset by higher cost of goods sold and higher sales and marketing expense.

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Calculated billings

The increase in calculated billings for the year and three months ended December 31, 2017 was driven by strong

adoption across our solutions globally.

Annualized recurring revenue

The increase in annualized recurring revenue for the year ended December 31, 2017 was driven by strong

adoption across our solutions globally, as evidenced by our calculated billings growth, and the increased shift of our

customers to a subscription pricing model.

Preliminary Guidance

Based on available information, we anticipate the following results for the year ending December 31, 2018

calculated in accordance with Accounting Standards Codification 605 and without giving effect to the impact of the

adoption of Accounting Standards Codification 606:

• year-over-year annualized recurring revenue growth of at least 30% compared to the year ended

December 31, 2017;

• calculated billings slightly up relative to the year ended December 31, 2017 due to shorter anticipated

contract lengths and the impact of the anticipated continued shift from perpetual to subscription licenses;

going forward, we believe that calculated billings may be less useful as a measure of the growth of our

business;

• year-over-year revenue growth of approximately 20% compared to the year ended December 31, 2017

driven by the anticipated continued transition to subscription licenses with respect to our vulnerability

management product line;

• slightly improved non-GAAP loss from operations compared to the year ended December 31, 2017; and

• cash flows from operating activities consistent with those for the year ended December 31, 2017.

Non-GAAP guidance excludes estimates for stock-based compensation expense, amortization of acquired

intangible assets and acquisition-related expenses. Rapid7 has provided a reconciliation of historical non-GAAP

financial measures to the most comparable GAAP measures above. A reconciliation of non-GAAP guidance measures

to the most comparable GAAP measures is not available on a forward-looking basis as a result of the uncertainty

regarding, and the potential variability of, many of the costs and expenses that we may incur in the future.

Corporate Information

We were initially incorporated in July 2000 in Delaware. Rapid7 LLC, a limited liability company organized

under the laws of the Commonwealth of Massachusetts, was formed in January 2004. In August 2004, pursuant to an

exchange agreement among Rapid7 LLC and the stockholders of Rapid7, Inc., the stockholders exchanged their

shares in Rapid7, Inc. for equity interests in Rapid7 LLC, after which Rapid7, Inc. was dissolved. In August 2008,

Rapid7 LLC was merged with and into Rapid7 LLC, a newly-formed Delaware limited liability company. Rapid7,

Inc. was reincorporated in Delaware in October 2011. In a series of transactions in November 2011, equity holders of

Rapid7 LLC exchanged their equity interests in Rapid7 LLC for capital stock in Rapid7, Inc. and Rapid7 LLC became

a wholly-owned subsidiary of Rapid7, Inc., which is the registrant.

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Our principal executive offices are located at 100 Summer Street, Boston, Massachusetts. Our telephone number is (617) 247-1717. Our website address is www.rapid7.com. The information contained on, or that can be accessed through, our website is not incorporated by reference into this prospectus supplement or the accompanying prospectus, and you should not consider any information contained on, or that can be accessed through, our website as part of this prospectus supplement or the accompanying prospectus or in deciding whether to purchase our common stock.

“Rapid7,” the Rapid7 logo, and other trademarks or service marks of Rapid7, Inc. appearing in this prospectus supplement and the accompanying prospectus are the property of Rapid7, Inc. This prospectus supplement and the accompanying prospectus contain additional trade names, trademarks and service marks of others, which are the property of their respective owners. Solely for convenience, trademarks and trade names referred to in this prospectus may appear without the ® or TM symbols.

Implications of Being an Emerging Growth Company

We qualify as an “emerging growth company” as defined in the Jumpstart Our Business Startups Act of 2012, or the JOBS Act. An emerging growth company may take advantage of relief from certain reporting requirements and other burdens that are otherwise applicable generally to public companies. We have chosen to take advantage of some but not all of these reduced burdens. To the extent that we continue to take advantage of these reduced burdens, the information that we provide stockholders may be different than you might obtain from other public companies in which you hold equity interests. As an emerging growth company:

• we have availed ourselves of the exemption from the requirement to obtain an attestation and report from our auditors on the assessment of our internal control over financial reporting pursuant to the Sarbanes-Oxley Act of 2002;

• we will provide less extensive disclosure about our executive compensation arrangements; and

• we will not require stockholder non-binding advisory votes on executive compensation or golden parachute arrangements.

We may use these provisions until the last day of our fiscal year following the fifth anniversary of our initial public offering. However, if certain events occur prior to the end of such five-year period, including if we become a “large accelerated filer,” our annual gross revenues exceed $1.07 billion or we issue more than $1.0 billion of non-convertible debt in any three-year period, we will cease to be an emerging growth company prior to the end of such five-year period.

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The Offering

Common stock offered by us 1,500,000 shares.

Common stock offered by selling

stockholders

3,680,000 shares (or 4,450,000 shares of common stock if the underwriters exercise their option to purchase additional shares from certain of the selling stockholders in full).

Option to purchase additional shares The underwriters have been granted an option to purchase up to an aggregate of 770,000 shares of our common stock from certain of the selling stockholders. This option is exercisable, in whole or in part, for a period of 30 days following the date of this prospectus supplement.

Common stock to be outstanding

immediately after this offering

45,357,005 shares.

Use of proceeds We currently expect to use the net proceeds from this offering for working capital and general corporate purposes. See “Use of Proceeds” on page S-12 for additional information. We will not receive any proceeds from the sale of shares of common stock by the selling stockholders.

Risk factors See “Risk Factors” on page S-10 and the other information included or incorporated by reference in this prospectus supplement and the accompanying prospectus for a discussion of factors you should carefully consider before deciding to invest in our common stock.

Nasdaq Global Market symbol “RPD”

The number of shares of our common stock to be outstanding after this offering is based on 43,857,005 shares of common stock outstanding as of September 30, 2017 and excludes:

• 4,778,250 shares of our common stock issuable upon the exercise of options to purchase our common stock under (i) our 2011 Stock Option and Grant Plan, (ii) our 2015 Equity Incentive Plan and (iii) the RevelOps, Inc. 2014 Stock Incentive Plan (which options were assumed by us in connection with our acquisition of RevelOps, Inc.), at a weighted-average exercise price of $9.61 per share;

• 2,069,623 shares of our common stock issuable upon the settlement of restricted stock units issued under our 2015 Equity Incentive Plan;

• 905,981 shares of our common stock reserved for future issuance under our 2015 Equity Incentive Plan; and

• 1,047,444 shares of our common stock reserved for future issuance under our 2015 Employee Stock Purchase Plan.

Except as otherwise indicated herein, all information in this prospectus supplement, including the number of shares that will be outstanding after this offering, does not assume or give effect to the exercise of options outstanding as of September 30, 2017.

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RISK FACTORS

Investing in our common stock involves a high degree of risk. You should carefully consider the risks and

uncertainties described below, together with all of the other information contained in this prospectus supplement, the

accompanying prospectus and in our filings with the Securities and Exchange Commission, or SEC, that we have

incorporated by reference in this prospectus supplement and the accompanying prospectus. In particular, we urge you to

consider carefully the factors set forth below and under Item 8.01 “Other Events—Risk Factors” in our Current Report on

Form 8-K filed with the SEC on January 23, 2018, which is incorporated by reference herein. If any of these risks actually

occur, our business, prospects, operating results and financial condition could suffer materially. In such event, the trading

price of our common stock could decline and you might lose all or part of your investment.

Risks Related to this Offering

We will have broad discretion in the use of proceeds from this offering and may invest or spend the proceeds in

ways with which you do not agree and in ways that may not yield a return.

We will have broad discretion over the use of proceeds from this offering. You may not agree with our decisions, and

our use of the proceeds may not yield any return on your investment in us. Our failure to apply the net proceeds of this

offering effectively could result in financial losses that could materially impair our ability to pursue our growth strategy,

cause the price of our common stock to decline or require us to raise additional capital.

Purchasers in this offering will incur immediate and substantial dilution in the book value of their investment as a

result of this offering.

Since the public offering price for our common stock in this offering is substantially higher than the net tangible book

value per share of our common stock outstanding prior to this offering, you will suffer immediate and substantial dilution

in the net tangible book value of the common stock you purchase in this offering. See the section entitled “Dilution” below

for a more detailed discussion of the dilution you will incur if you purchase shares in this offering.

The issuance of additional shares of our common stock could be dilutive to stockholders if they do not invest in

future offerings. In addition, we have a significant number of options to purchase shares of our common stock outstanding.

If these options are exercised, you may incur further dilution. Moreover, to the extent that we issue additional options or

warrants to purchase, or securities convertible into or exchangeable for, shares of our common stock in the future and

those options, warrants or other securities are exercised, converted or exchanged, stockholders may experience further

dilution.

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SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

This prospectus supplement, the accompanying prospectus, the documents incorporated by reference herein and therein and any free writing prospectus that we may authorize for use contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, or the Securities Act, and Section 21E of the Securities Exchange Act of 1934, as amended, or the Exchange Act. Any statements about our expectations, beliefs, plans, objectives, assumptions or future events or performance are not historical facts and may be forward-looking. These statements are often, but are not always, made through the use of words or phrases such as “may,” “could,” “should,” “expects,” “intends,” “plans,” “anticipates,” “believes,” “estimates,” “predicts,” “projects,” “potential,” “continue,” and similar expressions, or the negative of these terms, or similar expressions. Accordingly, these statements involve estimates, assumptions and uncertainties which could cause actual results to differ materially from those expressed in them. Given these risks and uncertainties, you should not place undue reliance on these forward-looking statements. We discuss many of these risks and uncertainties in greater detail in the risk factors incorporated by reference herein under the heading section captioned “Risk Factors” in this prospectus supplement, the accompanying prospectus and the documents incorporated herein and therein by reference.

Forward-looking statements are based on our management’s belief and assumptions and on information currently available to our management. These statements relate to future events or our future financial performance, and involve known and unknown risks, uncertainties and other factors that may cause our actual results, levels of activity, performance or achievements to be materially different from any future results, levels of activity, performance or achievements expressed or implied by these forward-looking statements.

Except as required by law, we assume no obligation to update these forward-looking statements, or to update the reasons actual results could differ materially from those anticipated in these forward-looking statements, even if new information becomes available in the future.

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USE OF PROCEEDS

We estimate the net proceeds to us from the shares offered by us in this offering will be approximately $30.9 million, after payment of underwriting discounts and commissions and estimated offering expenses payable by us.

We will not receive any of the proceeds from the sale of the shares of our common stock by the selling stockholders (including any shares sold by certain of the selling stockholders pursuant the underwriters’ option to purchase additional shares). However, we have agreed to pay expenses incurred by the selling stockholders in connection with the offering, other than the underwriting discounts and commissions.

The principal purposes of this offering are to increase our financial flexibility, facilitate an orderly distribution of our shares by selling stockholders and increase our public float. Although we have not yet determined with certainty the manner in which we will allocate the net proceeds of this offering from the sale of our common stock by us, we expect to use the net proceeds from this offering for working capital and other general corporate purposes, including to build out our future corporate headquarters in Boston, Massachusetts. We may also use a portion of the proceeds from this offering from the sale of our common stock by us for acquisitions or strategic investments in complementary businesses or technologies, although we do not currently have any plans for any such acquisitions or investments. We have not allocated specific amounts of net proceeds for any of these purposes.

The expected use of net proceeds from this offering from the sale of our common stock by us represents our intentions based upon our present plans and business conditions. We cannot predict with certainty all of the particular uses for the proceeds of this offering or the amounts that we will actually spend on the uses set forth above. Accordingly, our management will have significant flexibility in applying the net proceeds of this offering. The timing and amount of our actual expenditures will be based on many factors, including cash flows from operations and the anticipated growth of our business. Pending their use, we intend to invest the net proceeds of this offering in a variety of capital-preservation investments, including short- and intermediate-term, interest-bearing investment-grade securities.

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PRICE RANGE OF COMMON STOCK

Our common stock has been listed on The Nasdaq Global Market under the symbol “RPD” since July 17, 2015. Prior to that date, there was no public trading market for our common stock. The following table sets forth the reported high and low sales prices of our common stock for the periods indicated, as quoted on The Nasdaq Global Market:

High Low

Year Ended December 31, 2018:

First quarter (through January 25, 2018) $23.32 $18.50

High Low


First quarter $15.96 $12.20Second quarter $19.29 $14.36Third quarter $17.90 $14.75Fourth quarter $20.25 $17.08

High Low


First quarter $16.75 $ 9.05Second quarter $14.82 $10.82Third quarter $19.29 $11.55Fourth quarter $18.30 $10.63

On January 25, 2018, the closing price of our common stock as reported on The Nasdaq Global Market was $22.87 per share. As of such date, there were approximately 114 holders of record of our common stock. Because many of our shares are held by brokers and other institutions on behalf of stockholders, we are unable to estimate the total number of stockholders represented by these record holders.

DIVIDEND POLICY

We have never declared or paid, and do not anticipate declaring or paying in the foreseeable future, any cash dividends on our common stock. Any future determination as to the declaration and payment of dividends, if any, will be at the discretion of our board of directors, subject to applicable laws, and will depend on then existing conditions, including our financial condition, operating results, contractual restrictions, capital requirements, business prospects and other factors our board of directors may deem relevant.

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CAPITALIZATION

The following table shows our cash, cash equivalents and short-term investments and our capitalization as of September 30, 2017:

• on an actual basis; and

• on an as adjusted basis, giving effect to our issuance and sale of 1,500,000 shares of common stock in this offering, at a public offering price of $22.00 per share, after deducting underwriting discounts and commissions and estimated offering expenses payable by us.

You should read this table together with “Use of Proceeds” as well as our “Management’s Discussion and Analysis of Financial Condition and Results of Operations” and our financial statements and the related notes incorporated by reference into this prospectus supplement and the accompanying prospectus from our Annual Report on Form 10-K for the fiscal year ended December 31, 2016 and Quarterly Report on Form 10-Q for the quarter ended September 30, 2017, each as incorporated by reference herein.

As of September 30, 2017

Actual

As

Adjusted

(unaudited)

(in thousands, except

share data)

Cash, cash equivalents and short-term investments $ 83,880 $ 114,772

Stockholders’ Equity:Preferred stock, par value $0.01 per share; 10,000,000 shares authorized, no shares

issued or outstanding, actual and as adjusted — — Common stock, $0.01 par value: 100,000,000 shares authorized, actual and as

adjusted; 44,337,203 shares issued, actual; 43,857,005 shares outstanding, actual; 45,837,203 shares issued, as adjusted; 45,357,005 shares outstanding, as adjusted 439 454

Treasury stock, at cost, 480,198 shares at September 30, 2017 (4,645) (4,645) Additional paid-in capital 457,904 488,781Accumulated other comprehensive loss (23) (23) Accumulated deficit (421,909) (421,909)

Total stockholders’ equity 31,766 62,658

Total capitalization $ 31,766 $ 62,658

The number of shares our common stock set forth in the above table excludes:





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DILUTION

If you purchase shares in this offering, your interest will be diluted immediately to the extent of the difference between the public offering price per share and the net tangible book value per share of our common stock after this offering. Net tangible book value per share represents our total tangible assets less total liabilities, divided by the number of shares of our common stock outstanding.

As of September 30, 2017, our net tangible book value was $(68.6) million, or $(1.56) per share of common stock. After giving effect to our issuance and sale of 1,500,000 shares of common stock in this offering at a public offering price of $22.00 per share, after deducting underwriting discounts and commissions and estimated offering expenses payable by us, our as adjusted net tangible book value as of September 30, 2017 would have been $(37.7) million, or $(0.83) per share. This represents an immediate increase in as adjusted net tangible book value to existing stockholders of $0.73 per share of common stock and an immediate dilution to new investors purchasing common stock in this offering of $22.83 per share.

The following table illustrates this per share dilution to the new investors purchasing shares of common stock in this offering:

Public offering price per share $22.00Net tangible book value per share at September 30, 2017 $(1.56) Increase in net tangible book value per share attributable to this offering 0.73

As adjusted net tangible book value per share after this offering (0.83)

Dilution in net tangible book value per share to investors in this offering $22.83

The table and calculations above exclude:





To the extent that any outstanding options are exercised, new options or shares of restricted stock are issued under the 2015 Equity Incentive Plan, new shares are issued under our 2015 Employee Stock Purchase Plan, or we otherwise issued additional shares of common stock in the future, at a price less than the public offering price, there would be further dilution to the investors in this offering.

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SELLING STOCKHOLDERS

The selling stockholders are former holders of our preferred stock and current holders of our common stock

originally acquired through several private placements consummated prior to or concurrently with the completion of our

initial public offering, or IPO, in July 2015, as well as current holders of our common stock acquired through the exercise

of options granted under our 2011 Stock Option and Grant Plan. All shares of preferred stock converted into shares of our

common stock in connection with our IPO and, immediately prior to the closing of the IPO, holders of our Series D

preferred stock, including certain selling stockholders, received additional shares of our common stock pursuant to

provisions of our certificate of incorporation as in effect immediately prior to the closing of the IPO. In addition, entities

affiliated with Technology Crossover Ventures acquired 312,500 shares of our common stock in a private placement

concurrent with the completion of our IPO. The entities affiliated with Technology Crossover Ventures and the entities

affiliated with Bain Capital Venture Investors, LLC are associated with our directors, Timothy P. McAdam and J.

Benjamin Nye, respectively.

We are party to an investors’ rights agreement with the selling stockholders named in this prospectus supplement,

which provides the selling stockholders and the other holders of our common stock party thereto with certain rights with

respect to the registration of shares of common stock held by them under the Securities Act. Additional information

regarding such registration rights is contained in the accompanying prospectus under the heading “Description of Capital

Stock—Registration Rights.”

Except for the ownership of the shares of common stock that may be offered and sold by the selling stockholders, the

participation in the transactions described above, the investors’ rights agreement, the positions that Messrs. Matthews,

McAdam, Nye and Thomas hold on our board of directors and the positions that Mr. Thomas holds as an officer of our

company, the selling stockholders have not had any material relationship with us or our affiliates within the past three

years.

The table below, including the footnotes, sets forth the selling stockholders and other information regarding the

beneficial ownership of the shares of common stock held by each of the selling stockholders based on information

provided to us by the selling stockholders. Generally, a person “beneficially owns” shares of our common stock if the

person has or shares with others the right to vote those shares or to dispose of them, or if the person has the right to

acquire voting or disposition rights within 60 days. The percent of shares beneficially owned prior to the offering is based

on 44,053,736 shares of our common stock issued and outstanding as of December 31, 2017. The percent of shares

beneficially owned by the selling stockholders after the offering, assumes the sale of 1,500,000 shares of common stock

by us.

Shares Beneficially

Owned Prior to

Offering

Number of

Shares

to be Sold if

Underwriters’

Option is not

Exercised

Shares Beneficially

Owned After

Offering if

Underwriters’

Option is not

Exercised

Number of

Additional

Shares

to be Sold if

Underwriters’

Option

is Exercised

in Full

Shares Beneficially

Owned After

Offering if

Underwriters’ Option

is Exercised in Full

Name of Selling Stockholder Shares Percentage Shares Percentage Shares Percentage

Entities affiliated with Technology Crossover

Ventures(1) 6,538,043 14.8% 1,615,000 4,923,043 10.8% 385,000 4,538,043 10.0% Entities affiliated with Bain

Capital Venture

Investors, LLC(2) 6,682,713 15.2% 1,615,000 5,067,713 11.1% 385,000 4,682,713 10.3% Corey E. Thomas(3) 1,566,099 3.6% 200,000 1,366,099 3.0% — 1,366,099 3.0%

The Corey E. Thomas

Irrevocable Trust of 2016(4) 200,000 0.5% 50,000 150,000 0.3% — 150,000 0.3% Alan Matthews(5) 3,141,486 7.1% 200,000 2,941,486 6.5% — 2,941,486 6.5%

(1) The shares of common stock reported to us as beneficially owned prior to this offering by entities affiliated with Technology Crossover Ventures consist of (i) 4,278,661 shares directly held by TCV VII, L.P. (“TCV VII”), (ii) 2,222,011 shares directly held by TCV VII (A), L.P. (“TCV VII

(A)”), and (iii) 37,371 shares directly held by TCV Member Fund, L.P. (“Member Fund”). TCV VII is selling 1,056,897 shares of common stock (or

1,308,851 shares if the underwriters exercise their option to purchase additional shares in full), TCV VII(A) is selling 548,872 shares of common stock (or 679,717 shares if the underwriters exercise their option to purchase additional shares in

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full) and Member Fund is selling 9,231 shares of common stock (or 11,432 shares if the underwriters exercise their option to purchase additional

shares in full).

Technology Crossover Management VII, Ltd. (“TCM VII”), as the ultimate general partner of TCV VII and TCV VII(A) and a general partner of Member Fund, and Technology Crossover Management VII, L.P. (“Management VII”), as the direct general partner of TCV VII and TCV VII(A),

may be deemed to have the sole power to dispose or direct the disposition of the shares of common stock held by TCV VII and TCV VII(A) and,

with respect to TCM VII, the shares held by Member Fund and have the sole power to direct the vote of such shares. Messrs. Jay C. Hoag, Richard H. Kimball, John L. Drew, Jon Q. Reynolds, Jr., David L. Yuan, Robert W. Trudeau, Christopher P. Marshall, Timothy P. McAdam and John C.

Rosenberg are the Class A Directors of TCM VII and may be deemed to have the shared power to dispose or direct the disposition of the shares held

by TCV VII, TCV VII(A) and Member Fund and the shared power to direct the vote of such shares. Each of TCM VII and Management VII and the Class A Directors disclaims beneficial ownership of the shares of common stock owned of record by TCV VII, TCV VII(A) and Member Fund

except to the extent of their respective pecuniary interest therein. The address of these entities and individuals is c/o Technology Crossover Ventures, 528 Ramona Street, Palo Alto, California 94301.

(2) The shares of common stock reported to us as beneficially owned by entities affiliated with Bain Capital Venture Investors, LLC consists of (i) 5,841,509 shares of common stock held by Bain Capital Venture Fund 2007, L.P. (“BCVF”), (ii) 830,820 shares of common stock held by BCIP

Venture Associates (“BCIPVA”) and (iii) 10,384 shares of common stock held by BCIP Venture Associates-B (“BCIPVB” and, together with

BCVF and BCIPVA, the “Bain Capital Entities”). BCVF is selling 1,411,708 shares of common stock (or 1,748,245 shares if the underwriters exercise their option to purchase additional shares in full), BCIPVA is selling 200,783 shares of common stock (or 248,648 shares if the

underwriters exercise their option to purchase additional shares in full) and BCIPVB is selling 2,509 shares of common stock (or 3,107 shares if the

underwriters exercise their option to purchase additional shares in full). The governance, investment strategy and decision-making process with respect to the investments held by the Bain Capital Entities is directed by the Executive Committee of Bain Capital Venture Investors, LLC

(“BCVI”), which consists of Michael Krupka and Ajay Agarwal. By virtue of these relationships, BCVI and Messrs. Krupka and Agarwal may be deemed to share voting and dispositive power over the shares held by the Bain Capital Entities. The address of the Bain Capital Entities is 200

Clarendon Street, Boston, Massachusetts 02116.

(3) Includes (i) 1,436,486 shares of common stock issuable upon the exercise of options exercisable within 60 days of December 31, 2017 and (ii)

10,001 shares of common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2017.

(4) Represents 200,000 shares of common stock held directly by the Corey E. Thomas Irrevocable Trust of 2016, which is administered by independent

trustees.

(5) Includes (i) 15,174 shares of common stock issuable upon the exercise of options exercisable within 60 days of December 31, 2017 and (ii) 3,126,312 shares of common stock held directly by Mr. Matthews (1,800,000 of which are pledged as security for a loan).

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MATERIAL U.S. FEDERAL INCOME TAX CONSIDERATIONS FOR NON-U.S. HOLDERS

The following is a summary of the material U.S. federal income tax consequences to non-U.S. holders (as defined

below) of the acquisition, ownership and disposition of our common stock acquired pursuant to this offering. This

discussion is not a complete analysis of all potential U.S. federal income tax consequences relating thereto, does not

address the potential application of the Medicare contribution tax and does not address any estate or gift tax consequences

or any tax consequences arising under any state, local or foreign tax laws, or any other U.S. federal tax laws. This

discussion is based on the Internal Revenue Code of 1986, as amended, or the Code, Treasury Regulations promulgated

thereunder, judicial decisions and published rulings and administrative pronouncements of the Internal Revenue Service,

or IRS, all as in effect as of the date of this prospectus supplement. These authorities may change, possibly retroactively,

resulting in U.S. federal income tax consequences different from those discussed below. We have not requested a ruling

from the IRS with respect to the statements made and the conclusions reached in the following summary, and there can be

no assurance that the IRS will agree with such statements and conclusions.

This discussion is limited to non-U.S. holders who purchase our common stock pursuant to this offering and who

hold our common stock as a “capital asset” within the meaning of Section 1221 of the Code (generally, property held for

investment). This discussion does not address all of the U.S. federal income tax consequences that may be relevant to a

particular holder in light of such holder’s particular circumstances. This discussion also does not consider any specific

facts or circumstances that may be relevant to holders subject to special rules under the U.S. federal income tax laws,

including, without limitation, certain former citizens or long-term residents of the United States, partnerships or other

pass-through entities and the equity holders therein, “controlled foreign corporations,” “passive foreign investment

companies,” corporations that accumulate earnings to avoid U.S. federal income tax, banks, financial institutions,

investment funds, insurance companies, brokers, dealers or traders in securities, tax-exempt organizations, tax-qualified

retirement plans, persons subject to the alternative minimum tax, persons that own, or have owned, actually or

constructively, more than 5% of our common stock and persons holding our common stock as part of a hedging or

conversion transaction or straddle, or a constructive sale, or other risk reduction strategy.

If an entity or arrangement that is classified as a partnership for U.S. federal income tax purposes holds our common

stock, the U.S. federal income tax treatment of a partner will generally depend on the status of the partner and the

activities of the partnership. Partnerships holding our common stock and the partners in such partnerships are urged to

consult their tax advisors as to particular U.S. federal income tax consequences to them of holding and disposing of our

common stock.

PROSPECTIVE INVESTORS SHOULD CONSULT THEIR TAX ADVISORS REGARDING THE PARTICULAR

U.S. FEDERAL INCOME TAX CONSEQUENCES TO THEM OF ACQUIRING, OWNING AND DISPOSING OF

OUR COMMON STOCK, AS WELL AS ANY TAX CONSEQUENCES ARISING UNDER ANY STATE, LOCAL OR

FOREIGN TAX LAWS AND ANY OTHER U.S. FEDERAL TAX LAWS.

Definition of non-U.S. holder

For purposes of this discussion, a non-U.S. holder is any beneficial owner of our common stock that is not a “U.S.

person” or a partnership (including any entity or arrangement treated as a partnership and the equity holders therein) for

U.S. federal income tax purposes. A U.S. person is any of the following:

• an individual citizen or resident of the United States;

• a corporation (or other entity treated as a corporation for U.S. federal income tax purposes) created or organized

under the laws of the United States, any state thereof or the District of Columbia;

• an estate, the income of which is subject to U.S. federal income tax regardless of its source; or

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• a trust (1) whose administration is subject to the primary supervision of a U.S. court and which has one or more

U.S. persons who have the authority to control all substantial decisions of the trust, or (2) that has a valid

election in effect under applicable Treasury Regulations to be treated as a U.S. person.

Distributions on our common stock

If we make cash or other property distributions on our common stock, such distributions will constitute dividends for

U.S. federal income tax purposes to the extent paid from our current or accumulated earnings and profits, as determined

under U.S. federal income tax principles. Amounts not treated as dividends for U.S. federal income tax purposes will

constitute a return of capital and will first be applied against and reduce a holder’s tax basis in our common stock, but not

below zero. Any excess will be treated as gain realized on the sale or other disposition of our common stock and will be

treated as described under the section of this prospectus supplement titled “—Gain on disposition of our common stock”

below.

Subject to the discussion below regarding backup withholding and FATCA, dividends paid to a non-U.S. holder of

our common stock generally will be subject to U.S. federal withholding tax at a rate of 30% of the gross amount of the

dividends, or such lower rate specified by an applicable income tax treaty. To receive the benefit of a reduced treaty rate, a

non-U.S. holder must generally furnish to us or our paying agent a valid IRS Form W-8BEN or IRS Form W-8BEN-E (or

applicable successor form) including a U.S. taxpayer identification number and certifying such holder’s qualification for

the reduced rate. This certification must be provided to us or our paying agent prior to the payment of dividends and must

be updated periodically. If the non-U.S. holder holds the stock through a financial institution or other agent acting on the

non-U.S. holder’s behalf, the non-U.S. holder will be required to provide appropriate documentation to the agent, which

then will be required to provide certification to us or our paying agent, either directly or through other intermediaries.

Non-U.S. holders that do not timely provide the required certification, but that qualify for a reduced treaty rate, may

obtain a refund of any excess amounts withheld by timely filing an appropriate claim for refund with the IRS.

If a non-U.S. holder holds our common stock in connection with the conduct of a trade or business in the

United States, and dividends paid on our common stock are effectively connected with such holder’s U.S. trade or

business (and are attributable to such holder’s permanent establishment in the United States if required by an applicable

tax treaty), the non-U.S. holder will be exempt from U.S. federal withholding tax. To claim the exemption, the non-U.S.

holder must generally furnish a properly executed IRS Form W-8ECI (or applicable successor form).

Any dividends paid on our common stock that are effectively connected with a non-U.S. holder’s U.S. trade or

business (and if required by an applicable income tax treaty, are attributable to a permanent establishment maintained by

the non-U.S. holder in the United States) generally will be subject to U.S. federal income tax on a net income basis at the

regular U.S. federal income tax rates in the same manner as if such holder were a resident of the United States. A non-U.S.

holder that is a foreign corporation also may be subject to an additional branch profits tax equal to 30% (or such lower rate

specified by an applicable income tax treaty) of its effectively connected earnings and profits for the taxable year, as

adjusted for certain items. Non-U.S. holders should consult their tax advisors regarding any applicable income tax treaties

that may provide for different rules.

Gain on disposition of our common stock

Subject to the discussion below regarding backup withholding and FATCA, a non-U.S. holder generally will not be

subject to U.S. federal income tax on any gain realized upon the sale or other disposition of our common stock, unless:

• the gain is effectively connected with the non-U.S. holder’s conduct of a trade or business in the United States,

and if required by an applicable income tax treaty, is attributable to a permanent establishment maintained by the

non-U.S. holder in the United States;

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• the non-U.S. holder is a nonresident alien individual present in the United States for 183 days or more during the

taxable year of the disposition, and certain other requirements are met; or

• our common stock constitutes a “United States real property interest” by reason of our status as a United States

real property holding corporation, or USRPHC, for U.S. federal income tax purposes at any time within the

shorter of the five-year period preceding the disposition or the non-U.S. holder’s holding period for our common

stock, and our common stock is not regularly traded on an established securities market during the calendar year

in which the sale or other disposition occurs.

The determination of whether we are a USRPHC depends on the fair market value of our U.S. real property interests

relative to the fair market value of our other trade or business assets and our foreign real property interests. We believe we

are not currently and do not anticipate becoming a USRPHC for U.S. federal income tax purposes. However, there can be

no assurance that we will not become a USRPHC in the future.

Gain described in the first bullet point above generally will be subject to U.S. federal income tax on a net income

basis at the graduated U.S. federal income tax rates in the same manner as if such holder were a resident of the United

States. A non-U.S. holder that is a foreign corporation also may be subject to an additional branch profits tax equal to 30%

(or such lower rate specified by an applicable income tax treaty) of its effectively connected earnings and profits for the

taxable year, as adjusted for certain items. Non-U.S. holders should consult their tax advisors regarding any applicable

income tax treaties that may provide for different rules. Gain described in the second bullet point above will be subject to

U.S. federal income tax at a flat 30% rate (or such lower rate specified by an applicable income tax treaty), but may be

offset by certain U.S.-source capital losses (even though the individual is not considered a resident of the United States),

provided that the non-U.S. holder has timely filed U.S. federal income tax returns with respect to such losses.

Information reporting and backup withholding

Annual reports are required to be filed with the IRS and provided to each non-U.S. holder indicating the amount of

dividends on our common stock paid to such holder and the amount of any tax withheld with respect to those dividends.

These information reporting requirements apply even if no withholding was required because the dividends were

effectively connected with the holder’s conduct of a U.S. trade or business, or withholding was reduced or eliminated by

an applicable income tax treaty. This information also may be made available under a specific treaty or agreement with the

tax authorities in the country in which the non-U.S. holder resides or is established. Backup withholding, currently at a

24% rate, generally will not apply to payments to a non-U.S. holder of dividends on or the gross proceeds of a disposition

of our common stock provided the non-U.S. holder furnishes the required certification as to its non-U.S. status, such as by

providing a valid IRS Form W-8BEN, IRS Form W-8BEN-E or IRS Form W-8ECI, or certain other requirements are met.

Notwithstanding the foregoing, backup withholding may apply if the payor has actual knowledge, or reason to know, that

the holder is a U.S. person who is not an exempt recipient.

Backup withholding is not an additional tax. If any amount is withheld under the backup withholding rules, the

non-U.S. holder should consult with a U.S. tax advisor regarding the possibility of and procedure for obtaining a refund or

a credit against the non-U.S. holder’s U.S. federal income tax liability, if any.

Withholding on foreign entities

Sections 1471 through 1474 of the Code (commonly referred to as FATCA) impose a U.S. federal withholding tax of

30% on certain payments made to a “foreign financial institution” (as specially defined under these rules) unless such

institution enters into an agreement with the U.S. government to withhold on certain payments and to collect and provide

to the U.S. tax authorities substantial information regarding U.S. account holders of such institution (which includes

certain equity and debt holders of such institution, as well as certain account holders that are foreign entities with U.S.

owners) or an exemption applies. FATCA also generally will

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impose a U.S. federal withholding tax of 30% on certain payments made to a non-financial foreign entity unless such

entity provides the withholding agent a certification identifying the direct and indirect U.S. owners of the entity or an

exemption applies. An intergovernmental agreement between the United States and an applicable foreign country may

modify these requirements. Under certain circumstances, a non-U.S. holder might be eligible for refunds or credits of such

taxes. FATCA currently applies to dividends paid on our common stock. FATCA will also apply to gross proceeds from

sales or other dispositions of our common stock after December 31, 2018.

Prospective investors are encouraged to consult with their own tax advisors regarding the possible implications of

FATCA withholding on their investment in our common stock.

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UNDERWRITING

Barclays Capital Inc. and RBC Capital Markets, LLC are acting as joint book-running managers of this offering and representatives of the underwriters named below. Under the terms of an underwriting agreement, which we will file as an exhibit to our current report on Form 8-K and incorporate by reference in this prospectus supplement and the accompanying prospectus, each of the underwriters named below has severally agreed to purchase from us and the selling stockholders the respective number of shares of common stock shown opposite its name below:

Underwriters

Number of

Shares

Barclays Capital Inc. 1,709,400RBC Capital Markets, LLC 777,000KeyBanc Capital Markets Inc. 673,400Stifel, Nicolaus & Company, Incorporated 621,600Cowen and Company, LLC 518,000Raymond James & Associates, Inc. 414,400William Blair & Company, L.L.C. 259,000BTIG, LLC 207,200

Total 5,180,000

The underwriting agreement provides that the underwriters’ obligation to purchase shares of common stock depends on the satisfaction of the conditions contained in the underwriting agreement including:

• the obligation to purchase all of the shares of common stock offered hereby (other than those shares of common stock covered by their option to purchase additional shares as described below), if any of the shares are purchased;

• the representations and warranties made by us and the selling stockholders to the underwriters are true;

• there is no material change in our business or the financial markets; and

• we and the selling stockholders deliver customary closing documents to the underwriters.

Commissions and Expenses

The following table summarizes the underwriting discounts and commissions we and the selling stockholders will pay to the underwriters. These amounts are shown assuming both no exercise and full exercise of the underwriters’ option to purchase additional shares from certain of the selling stockholders. The underwriting fee is the difference between the initial price to the public and the amount the underwriters pay to us and the selling stockholders for the shares.

Us Selling Stockholders

No Exercise Full Exercise No Exercise Full Exercise

Per Share $ 0.99 $ 0.99 $ 0.99 $ 0.99Total $1,485,000 $1,485,000 $3,643,200 $4,405,500

The representatives have advised us that the underwriters propose to offer the shares of common stock directly to the public at the public offering price on the cover of this prospectus supplement and to selected dealers, which may include the underwriters, at such offering price less a selling concession not in excess of $0.561 per share. After the offering, the representatives may change the offering price and other selling terms.

The expenses of the offering to be incurred by us and the selling stockholders are estimated to be approximately $0.6 million (excluding underwriting discounts and commissions). We have agreed to pay

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expenses incurred by the selling stockholders in connection with the offering, other than the underwriting discounts and commissions. We have also agreed to reimburse the underwriters for certain of their expenses relating to clearance of this offering as set forth in the underwriting agreement, which are not expected to exceed $25,000. The underwriters have agreed to reimburse us for certain expenses in connection with this offering.

Option to Purchase Additional Shares

Certain of the selling stockholders have granted the underwriters an option exercisable for 30 days after the date of this prospectus supplement to purchase, from time to time, in whole or in part, up to an aggregate of 770,000 shares at the public offering price less underwriting discounts and commissions. To the extent that this option is exercised, each underwriter will be obligated, subject to certain conditions, to purchase its pro rata portion of these additional shares based on the underwriter’s percentage underwriting commitment in the offering as indicated in the table at the beginning of this Underwriting section.

Lock-Up Agreements

We have agreed that, without the prior written consent of Barclays Capital Inc. on behalf of the underwriters, we will not, during the period ending 75 days after the date of this prospectus supplement, or the restricted period: (1) offer, pledge, sell, contract to sell, sell any option or contract to purchase, purchase any option or contract to sell, grant any option, right or warrant to purchase, lend or otherwise transfer or dispose of, directly or indirectly, any shares of our common stock or any securities convertible into or exercisable or exchangeable for shares of our common stock; or (2) enter into any swap or other arrangement that transfers to another, in whole or in part, any of the economic consequences of ownership of our common stock; whether any such transaction described above is to be settled by delivery of our common stock or such other securities, in cash or otherwise. In addition, we have agreed that, without the prior written consent of Barclays Capital Inc. on behalf of the underwriters, we will not, during the restricted period, file any registration statement with the SEC relating to the offering of any shares of our common stock or any securities convertible into or exercisable or exchangeable for our common stock.

The restrictions described in the immediately preceding paragraph do not apply to: (1) the sale of shares of our common stock to the underwriters; (2) the issuance of shares of our common stock upon the exercise or conversion of a security outstanding on the date of this prospectus supplement and described herein or of which the underwriters have been advised in writing; (3) the issuance of shares of common stock, options to purchase shares of common stock, or other equity awards pursuant to our employee benefit plans disclosed herein; (4) the filing of a registration statement on Form S-8 or a successor form thereto; or (5) the sale or issuance or entry into an agreement to sell or issue shares of common stock in connection with our acquisition of one or more businesses, products or technologies (whether by means of merger, stock purchase, asset purchase or otherwise) or in connection with joint ventures, commercial relationships or other strategic transactions, provided that the aggregate number of shares of common stock that we may sell or issue or agree to sell or issue pursuant to this clause shall not exceed 5% of the total number of shares of common stock issued and outstanding immediately following the completion of this offering, and provided further that the recipient of such shares of common stock agrees to be bound in writing by an agreement of the same duration and terms as agreed to by us.

In addition, all of our directors and executive officers and the selling stockholders have agreed that, without the prior written consent of Barclays Capital Inc. on behalf of the underwriters, they will not, during the restricted period: (1) offer, pledge, sell, contract to sell, sell any option or contract to purchase, purchase any option or contract to sell, grant any option, right or warrant to purchase, lend or otherwise transfer or dispose of, directly or indirectly, any shares of our com

Documents

Rapid7, Inc. - StifelRapid7, Inc. Common Stock We are offering 1,500,000 shares of our common stock, and the selling stockholders identified in this prospectus supplement, including