Company Overview

February 9, 2022
 Disclaimers
This presentation contains forward-looking statements. All statements contained in this presentation other than statements of historical facts, including, without limitation, statements
regarding our market opportunity, demand for our product and service offerings, expectations regarding our annualized recurring revenue (ARR) and growth,  ARR opportunity for an
average-sized customer, ARR growth per customer, revenue growth, non-GAAP operating margin expansion, free cash flow, and our other non-GAAP measures, our business strategy,
plans and objectives for future operations and expectations regarding non-GAAP targets, our future financial and business performance for the first quarter and full-year 2022, the
assumptions underlying such guidance and the anticipated impact of COVID-19 on our guidance, business, financial condition and results of operations, are forward-looking statements.
Our use of the words “anticipate,” “believe,” “continue,” “estimate,” “expect,” “intend,” “may,” “will” and similar expressions are intended to identify forward-looking statements.  The events
described in our forward-looking statements are subject to a number of risks and uncertainties, assumptions and other factors that could cause actual results and the timing of certain
events to differ materially from future results expressed or implied by the forward-looking statements. Risks that could cause or contribute to such differences include, but are not
limited to, risks arising from the ongoing COVID-19 pandemic, fluctuations in our quarterly results, failure to meet our publicly announced guidance or other expectations about our
business, 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 integrate acquired companies, including IntSights, our ability to operate in
compliance with applicable laws as well as other risks and uncertainties set forth in the “Risk Factors” section of our most recent Quarterly Report on Form 10-Q filed with the Securities
and Exchange Commission on November 4, 2021 and in the 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 expressed in any forward-looking statements we may
make. Except as required by law, we undertake no obligation to update any forward-looking statements to reflect events or circumstances after the date of such statements.  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.

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.

This presentation also contains certain non-GAAP financial measures as defined by the SEC rules. These non-GAAP financial measures are in addition to, and not a substitute for or
superior to, measures of financial performance prepared in accordance with GAAP. There are a number of limitations related to the use of these non-GAAP financial measures versus
their nearest GAAP equivalents. For example, other companies may calculate non-GAAP financial measures differently or may use other measures to evaluate their performance, all of
which could reduce the usefulness of our non-GAAP financial measures as tools for comparison. Please refer to our February 9, 2022 press release for additional information as to why
we believe these non-GAAP financial measures are useful to investors and others in assessing our operating results. As required by Regulation G, we have provided a reconciliation of
those measures to their most directly comparable GAAP measures, which is available in the end notes to this presentation. However, the reconciliation of non-GAAP guidance measures
to the most comparable GAAP measures does not reflect any items that are unknown at this time, such as litigation-related expenses, which we are not able to predict without
unreasonable effort due to their inherent uncertainty.

2
 Rapid7 Snapshot

Attractive Investing in
Strong Recurring High Quality
Customer Profitable
Revenue Growth of Revenue
Economics Growth

Recurring revenue Expansion of

ARR growth of 17% growth Non-GAAP
38% YoY 1 92% of total in ARR per Operating Margin
1
revenue customer 1 and Free Cash Flow
Projected in 2022 2

Attractive Projected ARR growth of 24% in 2022 2

Prospects Projected Revenue growth of 28% in 2022 2

1
As of Q4 2021 3
2
Based on FY 2022 guidance provided as of February 9, 2022. Growth rates are at the mid-point of the guidance range.
Managing Risk and Enabling Innovation

Data keeps our Accelerated change Security needs to

We trust security
connected society makes it tougher to keep up with the
teams to protect
functioning. stay ahead of risks. pace of innovation.
our data.

Organizations need best-in-class security that is both sophisticated and accessible.

4
Delivering on Our Mission

Unite teams and tools with award-winning

Best-in-Class
cloud products delivering visibility,
Technology
Make analytics, and automation.

best-in-class
security Enrich customer experiences with broad
Unified Cloud
operations Platform
environment visibility, seamless
integrations and ease of scaling.
accessible &
achievable
for all. Expertise &
Deliver leading products and expertise built
on insights from our experienced security
Community researchers and the security community.

5
Rapid7 Insight Platform

United teams work

smarter, not harder.

Our cloud platform helps Security,

IT, and Development teams reduce
risk across their entire connected
environment.

Unified access centrally manages

vulnerabilities, monitors for
misconfigurations and malicious
behavior, investigates and shuts
down attacks, or automates
operations.

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 Landing and Expanding Across Multiple Pillars
SECURITY TRANSFORMATION SOLUTIONS1

Threat Detection & Cloud Vulnerability Risk

Response Security Management

Threat Intelligence

Intelligent Automation

SHARED INSIGHT ENGINE

Collection,
SHARED Data, Analytics Services
INSIGHT ENGINE
Collection, Data, Analytics Services

1
7
Security transformation solutions consist of our incident detection & response, cloud security, application security, threat intelligence and security orchestration and automation response product offerings.
 ACCESSIBILITY TO INSIGHT VIA TAILORED SECOPS PILLARS

Threat Detection Vulnerability Risk

Cloud Security
& Response Management

SHARED INSIGHT ENGINE

AUTOMATION Orchestration Workflow Action

Attacker Vulnerability Policy Identity

ANALYTICS User Behavior
Behavior Prioritization Compliance Governance
Remediation

Unstructured &
DATA Searchable
Structured
Long Term Archival High Volume Integrations

COLLECTION Endpoint Cloud Logs Network Apps API

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Best-in-Class Threat Detection & Response
Broad Visibility Across Cloud and
On-premise.

Detection-oriented Analytics.

Automated Containment & Response.

Automation Custom Escalation Workflows

Analytics UBA ABA ML

Data Integrations

Collection Cloud Endpoint Network

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Best-in-Class Cloud Security
Multi-cloud Risk Visibility & Analytics.

Extensible & Customizable to Connect

Security and DevOps Teams.

Real-time Automated Remediation.

Automation Native & Integrated

Analytics CIEM CWPP CSPM

Data AWS Azure GCP OCI

Collection Cloud

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Best-in-Class Vulnerability Risk Management
Broad Visibility Across Traditional and
Modern Environments

Prioritize Risk with Advanced Analytics

Automation-assisted Remediation

Custom
Automation Processes
Workflows

Attacker Vulnerability
Analytics Behavior Prioritization

Data Searchable Integrations

Collection Cloud Endpoint Network

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 Massive Market Opportunity
$40bn TOP DOWN (2022) BOTTOM UP (2022)

UNDER-PENETRATED ~$37 bn
$30bn OPPORTUNITY

~$29 bn
$20bn SECURITY ~$500k 2
TRANSFORMATION ARR Opportunity for
SECURITY an average-sized
TRANSFORMATION customer
$10bn

VM
VM
Global Addressable
IDC 1 Customer Opportunity
3
> 74,000
1
Based on IDC Forecasts (WW Device Vulnerability Management 2019-2026, WW Cybersecurity AIRO 2018-2025, WW Security as a Service 2021-2025, WW Cloud Workload Security 2019-2025, WW Threat Intelligence Security Services 2018-2023)
2
The future financial results presented are hypothetical amounts for achievement of certain scenarios and are not projections, guidance or an outlook for Rapid7’s future financial results 12
3
Based on Dun & Bradstreet Hoovers global business data
 Extensive Partner Ecosystem

80+ DATA
COLLABORATION
DATA
WORKFLOW
PARTNERS
DATA
INGESTION
PARTNERS
Platform PARTNERS

Integrations • Two-way data sharing • IT security integration • Enhances analytics

• Streamlines correction • Enables detection
with Partners • ‘Single pane of glass’
• Enhanced platform
• Improves IT
efficiencies
• Simplifies
investigations
value

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Rapid7 Global Threat Intelligence Community
Insight Cloud Threat Intelligence Intelligence Sharing Attacker KB

Leading External Cyber Threat Affiliate Member, Vulnerability Database

Global customer base
Intelligence Capabilities Board & Committee Seats & Community

Metasploit &
Project Heisenberg Project Sonar Rapid7 Research
Velociraptor

Penetration Testing & Endpoint

Global Honeypot Network Global Internet Scanning Threat Research
Forensics Tools & Communities

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Rapid7 Leadership Among Analysts

Positioned as Positioned as Recognized as Positioned as Positioned as

Leader amongst Leader in 2021 Gartner Peer Visionary in 2021 Leader amongst
Vulnerability Risk and 2020 Magic Insights Magic Quadrant Midsize Managed
Management Quadrant for Customers’ for Application Security Services
(VRM) vendors in Security Choice for Security Testing vendors in 2020
2019 and 2018 Information & Vulnerability Forrester Wave.
Forrester Wave Event Management and
Management SIEM in 2020
(SIEM)

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Rapid7 for Social Good Beyond ESG
Diversity, Equity, & Inclusion
RAPID7 CORE VALUES Leverage diverse hiring practices and data-driven focus to advance a diverse
workforce, inclusive culture, and equitable pay. Recognized in Bloomberg
Gender Equality Index 2018, 2019, 2020, 2021, 2022.

Environment & Climate Change

Bring You Focus on reducing environmental impact by minimizing greenhouse gas emissions,
Thrive by celebrating individuality and diverse perspectives
reducing & responsibly disposing of waste, and creating more sustainable workplaces.

Be an Advocate
Relentlessly champion our customers to propel the security Corporate Governance
industry forward
High ethical standards for governance set by the board of directors.
Challenge Convention
Forge new paths with foresight, discipline, and determination
Community Engagement & Social Impact
Impact Together
Actively support, collaborate with, and learn from each other Giving back to our communities through partnerships with STEM and inclusion-focused
programs, charitable giving, and employee volunteerism.
Never Done
Pursue personal and professional excellence through
continuous learning
Non-Profit Support
Offering solution discounts to eligible Non-profits so they can focus more of their
resources pursuing the good they do in the world.

16
Financial Overview

17
 Sustained Revenue Growth

• Q4 2021 revenue growth

of 34% year-over-year

• Revenue CAGR
(2017-2021): 28%

• Non-GAAP operating margin

improvement over time

18
2017 numbers are under ASC 605 and 2018 and beyond numbers are under ASC 606
Annualized Recurring Revenue

%
• ARR grew by 38% year- : 33
GR
CA
over-year in Q4 2021

• ARR CAGR of 33% from

Q4 2018 to Q4 2021

19
 Upsells & Cross-Sells Drive ARR Per Customer Growth

• ARR per customer was R: 18%

CAG
approximately $58.3k in
Q4 2021

• ARR per customer CAGR of 18%

from Q4 2018 to Q4 2021

20
ARR per customer is based on the new customer count methodology provided at Rapid7’s 2021 Investor Day on March 10, 2021.
 Significant Long-Term ARR Per Customer Opportunity
~$500k

ARR OPPORTUNITY FOR AN AVERAGE-SIZED CUSTOMER

AppSec

• Our recurring revenue potential for an Automation

Automation
average-sized customer is $500k per year
Threat Intelligence

VM
• ARR per customer was approximately
$58.3k in Q4 2021 ~8.5x
D&R

$58.3k CloudSec
ARR/CUSTOMER

The future financial results presented are hypothetical amounts for achievement of certain scenarios and are not projections, guidance or an outlook for Rapid7’s future financial results 21
Focused on Long-term Profitability Improvement
Expenses and Operating Income as % of Revenue (non-GAAP)

Gross Margin Sales & Marketing Research & General & Operating Income
(non-GAAP) (non-GAAP) Development Administrative (non-GAAP)
(non-GAAP) (non-GAAP)

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 Powerful Land And Expand Model
Compelling Track Record of Customer Acquisition, Retention and Expansion

Land
ARR
+18% Growth
YoY
Customer Growth 1

+38%
Expand YoY
ARR Growth 1

+17%
YoY ARR
per Customer Growth 1

1
23
As of Q4 2021
 Guidance | Q1 2022 and Full-Year 2022
Rapid7 anticipates Annualized Recurring Revenue, Revenue, Non-GAAP (loss) income from operations, non-GAAP net
(loss) income per share and free cash flow to be in the following ranges:

Q1 2022 Full Year 2022

v
Annualized Recurring Revenue $740 to $750m

Annualized Recurring Revenue Growth 24% to 25%

Revenue $153 to $155m $682 to $690m

Revenue Growth 30% to 32% 27% to 29%

Non-GAAP (Loss) Income From Operations 1 ($7) to ($5m) $17 to $24m

Non-GAAP Net (Loss) Income Per Share 1 $(0.18) to $(0.15) $0.05 to $0.16

Weighted-average Shares Outstanding 58.3 m* 60.9 m*

Free Cash Flow $40 to $45m

See End Notes for additional information and definitions
* Weighted average shares outstanding for the first quarter 2022 represent basic shares outstanding given our projected non-GAAP net loss and diluted shares outstanding for the full-year 2022 given our
projected range of non-GAAP net income
1
A reconciliation of non-GAAP guidance measures to the most comparable GAAP measures is provided in the supplemental financial tables. The reconciliation does not reflect any items that are unknown 24
at this time, such as litigation-related expenses, which we are not able to predict without unreasonable effort due to their inherent uncertainty.
Supplemental

25
 GAAP to Non-GAAP Reconciliations: Q4 2021

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

 GAAP to Non-GAAP Reconciliations: Q4 2020

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

 GAAP to Non-GAAP Guidance Reconciliations: Q1 & Full-Year 2022

The reconciliation does not reflect any items that are unknown at this time, such litigation-related expenses, which we are not able to predict without unreasonable effort due to their inherent uncertainty. As a result, the
estimates shown for Anticipated GAAP loss from operations, Anticipated GAAP net loss and Anticipated GAAP net loss per share are expected to change.

(All amounts in millions, except per share data)

 GAAP to Non-GAAP Guidance Reconciliations: Full-Year 2022

(All amounts in millions, except per share data)

End Notes
Annualized Recurring Revenue (ARR)
• Annualized Recurring Revenue (ARR) is defined as the annual value of all recurring revenue related to contracts in place at the end of the period. ARR should be viewed independently
of revenue and deferred revenue as ARR is an operating metric and is not intended to be combined with or replace these items. ARR is not a forecast of future revenue and can be
impacted by contract start and end dates and renewal rates, and does not include revenue reported as perpetual license or professional services revenue in our consolidated
statement of operations.

Recurring Revenue
• Recurring revenue is defined as revenue from the sale of term software licenses, content subscriptions, managed services, cloud-based subscriptions and maintenance and support
calculated as % of total revenue.

Customer
• A Customer is defined as any entity that has an active recurring revenue contract as of the specified measurement date, excluding InsightOps and Logentries only customers with a
contract value less than $2,400 per year.

ARR per Customer

• ARR per Customer is defined as ARR divided by the number of Customers at the end of the period.

Non-GAAP metrics
• Non-GAAP gross margins represent the GAAP gross profit, excluding stock-based compensation expense and amortization of acquired intangible assets calculated as a % of revenue.
See GAAP to Non-GAAP reconciliation.
• Operating expenses and operating income margin presented are on a non-GAAP basis and exclude stock-based compensation expense, amortization of acquired intangible assets,
and certain other items such as acquisition-related expenses and litigation-related expenses.
• Free cash flow is defined as net cash flow provided by (used in) operations less purchases of property and equipment and capitalization of internal-use software costs.

Guidance
• Guidance for the first quarter and full-year 2022 does not include any potential impact of foreign exchange gains or losses.
• Non-GAAP guidance excludes estimates for stock-based compensation expense, amortization of acquired intangible assets, amortization of debt issuance costs and certain other
items. A reconciliation of non-GAAP guidance measures to the most comparable GAAP measures is provided in the financial statement tables included in these End Notes. The
reconciliation does not reflect any items that are unknown at this time, such as litigation-related expenses for the first quarter and full-year 2022, which we are not able to predict
without unreasonable effort due to their inherent uncertainty.