NASDAQ: CSOD

As of August 5, 2019

Global Leader in Cloud-Based Learning and HCM

This presentation includes forward-looking statements. These statements relate to, among other things, our future financial and operating performance, including our GAAP and non-GAAP guidance, the growth of the learning and human capital management market, our business strategy, and our plans and objectives for future operations. In light of the risks and uncertainties outlined below, the future events and circumstances discussed in this presentation may not occur, and actual results could differ materially from those anticipated or implied in the forward-looking statements. The Company has based these forward-looking statements largely on its current expectations and projections about future events and financial trends affecting its business. Forward-looking statements should not be read as guarantees of future performance or results, and will not necessarily be accurate indications of the times at, or by, which such performance or results will be achieved. Forward-looking statements are based on information available at the date of this presentation and management’s good faith belief as of such date with respect to future events, and are subject to risks and uncertainties that could cause actual performance or results to differ materially from those expressed in or suggested by the forward-looking statements. Important factors that could cause such differences include, but are not limited to:

• Statements regarding the Company’s business strategies;

• The Company’s anticipated future operating results and operating expenses;

• The Company’s ability to attract new clients to enter into subscriptions for its solution;

• The Company’s ability to service those clients effectively and induce them to renew and upgrade their deployments of the Company’s solution;

• The Company’s ability to expand its sales organization to address effectively the new industries, geographies and types of organizations the company intends to target;

• The Company’s ability to accurately forecast revenue and appropriately plan its expenses; market acceptance of enhanced solutions, alternate ways of addressing learning and talent management needs or new technologies generally by the Company and its competitors; continued acceptance of SaaS as an effective method for delivering learning and talent management solutions and other business management applications; the attraction and retention of qualified employees and key personnel;

• The Company’s ability to protect and defend its intellectual property; costs associated with defending intellectual property infringement and other claims; events in the markets for the Company’s solution and alternatives to the Company’s solution, as well as in the United States and global markets generally; future regulatory, judicial and legislative changes in the Company’s industry; changes in the competitive environment in the Company’s industry and the markets in which the Company operates; and other factors discussed under “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in the Company’s periodic reports filed with the Securities and Exchange Commission (the “SEC”).

Forward-looking statements speak only as of the date of this presentation. You should not put undue reliance on any forward-looking statement. The Company assumes no obligation to update any forward-looking statements to reflect actual results, changes in assumptions or changes in other factors affecting future performance or results, except to the extent required by applicable laws. If the Company updates one or more forward-looking statements, no inference should be drawn that it will make additional updates with respect to those or other forward-looking statements.

In addition to U.S. GAAP financials, this presentation includes certain non-GAAP financial measures. These non-GAAP financial measures are in addition to, not a substitute for or superior to, measures of financial performance prepared in accordance with U.S. GAAP. Please see the discussion of these non-GAAP financial measures and their reconciliations to the most directly comparable U.S. GAAP measures at the end of this presentation.

Safe Harbor

2

The Transformation

3

Second Quarter 2019 AchievementsFive-Point Strategic Transformation Plan Has Driven Significant Value

1

2

3

4

5

Strategic Plan Value Creation

Focus on recurring revenue and exit enterprise service delivery

Q2 Subscription revenue growth of 16% YoY (17% cc YoY) Subscription revenue 93% of total revenue, up from 87% in 2018

Improve operating margins and cash flow

Q2 Operating Margin improved to 12% from 10% in 2018 Unlevered FCF margin improved to 7% from 6% in 2018

Create new recurring revenue streams, including aggressively entering the content market

Strong growth in average deal sizes and uptick in large deals Signed first multi-million-dollar Content Anytime deal

Bolster the team New, tenured marketing leadership

Improve governance

Source: Q2 2019 results as of June 30, 2019

Successful Exit from Enterprise Services

Total Revenue($ in millions)

$20 $18 $9

$96 $115 $133

Q2 2017 Q2 2018 Q2 2019

Services Subscription

$116$133

$142

5

Key Metrics: The Cornerstone Transformation

$439$510

$579.5 - $589.5

2017 2018 2019E

Annual Recurring Revenue (ARR)

Note: FY19 Guidance ranges as of August 5, 2019. GAAP to Non-GAAP Reconciliation is located in the Appendix

$482

$538

$566.5 - $571.0

2017 2018 2019E

Total Revenue

$397 $473

$539.5 - $544.0

2017 2018 2019E

Subscription Revenue

6%

12%14-15%

2017 2018 2019E

Non-GAAP Operating Margin

9%12%

15-16%

2017 2018 2019E

Unlevered FCF Margin

($ in millions)

6

Cornerstone Today

7

Global ReachCLIENTS

3,600+USERS

40M+COUNTRIES

190+LANGUAGES

40+OFFICES

20+

Sunnyvale

Santa Monica

Sao Paulo

MadridParis

London

Stockholm

DusseldorfMunich

Tel Aviv

Bangalore

MumbaiHong Kong

Tokyo

Sydney

Auckland

Singapore

Amsterdam

Note: User and client count figures exclude PiiQ, Cornerstone for Salesforce, Workpop Inc. and Grovo Learning, Inc.As of June 30, 2019

Salt Lake City

New York City San Francisco

Mexico City

8

Marquee Clients Around the WorldAPJUS & LATAM EMEA

9

A Decade of Sustained Revenue Growth

IPO

$19.6 $29.3 $46.6 $75.5

$117.9

$185.1

$263.6

$339.7

$423.1

$482.0 $537.9

2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018

RevenueIn USD $ Millions

10

Strong Growth in the Base

168 280

481

805

1,237

1,631

2,153

2,595

2,918

3,250

3,535

2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018

Client Growth

2.13.3

4.9

7.5

10.6

14.0

18.1

23.8

29.9

35.3

40.2

2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018

User Growth(in Millions)

Note: User and client count figures exclude PiiQ, Cornerstone for Salesforce, Workpop Inc. and Grovo Learning, Inc.; Numbers updated as of 12/31/18 11

COMPLETENESS OF VISION

ABI

LITY

TO E

XEC

UTE

CHALLENGERS LEADERS

NICHE PLAYERS VISIONARIES

Cornerstone is the Market Leaderin Talent Management

SOURCE: Gartner (September 2018)

2018 Magic Quadrant for Talent Management Suites

Cegid

Saba (TalentSpace)

Skillsoft (SumTotal Systems)

Saba (Saba Cloud)

Haufe

SAP (SuccessFactors)

Talentsoft

PageUp

1212

The Solution

13

Skilled Jobs Unskilled Jobs

Skilled Workers Unskilled Labor

The Skills Divide is Real

RECRUITING SUITE• APPLICANT TRACKING

• CAREER SITES

• INTERVIEW MANAGEMENT

• ENABLE FRONTLINE MANAGERS

• CANDIDATE SCREENING

• NEW HIRE ONBOARDING

PERFORMANCE SUITE• CONTINUOUS DEVELOPMENT

• PREDICTIVE SUCCESSION PLANNING

• INTERNAL TALENT MOBILITY

• SMART COMPENSATION PLANNING

• INTUITIVE DATA VISUALIZATIONS

• PULSE ENGAGEMENT SURVEYS

LEARNING SUITE• LEARNING MANAGEMENT

• CERTIFICATIONS

• CONNECT & COLLABORATE

• INSIGHTS

• LEARNING EXPERIENCE

• CONTENT

HR SUITE• CENTRALIZED VIEW OF GLOBAL WORKFORCE

• HEADCOUNT PLANNING

• ANALYTICS & REPORTING

• BENCHMARK TALENT METRICS

• FLEXIBLE DEPLOYMENT

• SIMPLE & INTUITIVE UI

Cornerstone’s HCM Product SuitesA Unified Platform for the Skills Economy

15

Cornerstone Recruiting

• Understand your hiring pipeline

• Source and manage candidates

• Efficiency with automation

• Provide a positive candidates experience

• Promote talent mobility and development

Next-generation Recruiting to Hire Across the Skills Divide

16

Cornerstone Learning

• Configurable, yet simple Learning Management

• The next generation of Learning Experience

• Content you can’t get anywhere else

The World’s Most Robust Learning Platform

17

Cornerstone Performance

• Maintain alignment to drive business outcomes

• Foster a culture of talent mobility

• Reward and recognize high performers

Drive results with Continuous Performance Development

18

Cornerstone HR

• View & manage all employee records in one place

• Empower employees to manage personal data

• Proactively seek out top performers

• Create headcount forecasts

• Get a global view of your organization

Centralizes HR Administration into a Single, Modern System

19

Collections of Content You Can’t Get Anywhere Else

Wide Partner Ecosystem

with a variety of modalities, topics, and titles

Intelligently Curated Subscriptions

built to solve specific business needs

[Playlists included with each subscription]

Seamlessly Purchased & Loaded

for enhanced user experience

[We handle metadata, thumbnails, content upload]

Subject-matter Experts

to listen to your business needs and recommend

the right content

Client

Curated Subscriptions

Integrated with LXP

Content Consultants

Best-of-breedPartners

20

Accelerating Growth:$40B Market Opportunity

21

22

Expanding Market Opportunity

Source: Training Industry Report (2017); Company estimates and WW HCM Apps Forecast, IDC WW Tracker, June 2018 Report

HCM + Content: $40B

*Talent Management – $7B

*Learning – $1.5B

9-11%GROWTH

*Performance – $1.5B

5%GROWTH

*Recruiting – $4B

16%GROWTH

11% GROWTH

HCM – $16B 10%GROWTH

1. Installed Base

2. Content

3. Recruiting

4. Cornerstone HR

5. APJ

Growth Drivers

23

Installed Base Opportunity

0

500

1,000

1,500

2,000

2,500

3,000

3,500

Learning Performance Recruiting Cornerstone HR

Existing Client Penetration Client Opportunity

Num

ber

of C

lient

s

50% penetrationamong other suites results in incremental

$500MARR opportunity

Calculated based on 3,535 clients with approximately 11,400 users on average

Four Key Pillars, each a suite, and half of it GREENFIELD

24

Content at ScaleSizing the Content Opportunity for Cornerstone

3x+Content AnytimeRPU of Learning

~$250MARR Opportunity Today

What We’ve Seen

Today’s ARR Opportunity

25

Recruiting GrowthGrowing adoption of the Recruiting Suite

26

Opportunity Exists to Capitalize on the Managing Director Model

We have shifted to a country-specific GTM approach

Australia & New Zealand Japan Asia

Singapore (ASEAN)

Hong Kong

South Korea

27

Cornerstone HR’s Impact on Deals in EMEA

*EMEA deals in 2018Average deal values converted from local currency to USD

Average Suites Purchased

Average RPU

• EMEA clients that purchased Cornerstone HR on average buy ~2x more product suites

• Cornerstone HR increases ARPU by ~2x

1.7

3.6

Without Cornerstone HR With Cornerstone HR

~$30

~$65

Without Cornerstone HR With Cornerstone HR

28

14% 12% 15% 13%5%

14% 19% 13% 13% 18%

22%19% 19%

16%

16%13%

13%10% 9%

7%

64% 69% 66% 71%79% 73% 68%

77% 78% 75%

0%

10%

20%

30%

40%

50%

60%

70%

80%

90%

100%

TCPU Public Admin FinancialServices

Retail Higher Ed Other Services Healthcare Manufacturing High-Tech AMC

Replace Upgrade Do Nothing

Source: Sierra Cedar 2015–2016 HR Systems Survey 18th Annual Edition

Finding the Blue Ocean in Core HRCornerstone HR is addressing the “do nothing” segment vs. upgrade (primarily PeopleSoft) & replace (primarily Workday & SAP)

29

FY2019 Guidance Summary

30

$119

$136.0

$15

$6

-

$20M

$40M

$60M

$80M

$100M

$120M

$140M

Q3 2018 Q3 2019 Guidance

Subscription Services

$473

$541.8

$65

$27

-

$100M

$200M

$300M

$400M

$500M

$600M

FY18 FY19 Guidance

Subscription Services

2019 Revenue Guidance

$135.0 – $137.0 $539.5 – $544.0.

$134M

$568.8M$142.0M

$538M

Third Quarter Full Year

~(58%)

$566.5 – $571.0$141.0 – $143.0

(Dollar in millions)

Note: Reflects guidance issued as of August 5, 2019. 31

2019 Guidance

OTHER:1. GBP to USD 1.22

EUR to USD 1.12

2. 5% FX Δ in GBP = $1 ARR / $2 Revenue5% FX Δ in EUR = $4 ARR / $1 Revenue

3. Net Interest Expense(4):• GAAP $14• Non-GAAP $10

4. Cash Interest Paid $17

5. Shares outstanding increases from 60M to 66M when Net Income is positive

6. Income tax expense $3

7. SBC as % of revenue ~13%, versus prior year of 11%

8. Capex ~3% of revenue

(Dollar in millions)

Notes: 1. Reflects guidance issued as of May 6, 2019.2. Reflects guidance issued as of August 5, 2019.3. Denotes a non-GAAP metric4. Net Interest Expense is Gross Interest Expense less Interest Income

2018 Actual Prior 2019 Guidance(1)

Current 2019 Guidance(2)

ARR(3)Growth

$510 $575 - $59013-16% / 14-16% CC

$579.5 - $589.514-16% / 14-16% CC

Total RevenueGrowth

$538 $562 - $5704-6% / 5-7% CC

$566.5 - $571.05-6% / 7-8% CC

Subscription RevenueGrowth

$473 $537 - $54514-15% / 14-16% CC

$539.5 - $544.014-15% / 16-17% CC

Professional Consulting Services

Revenue$65 Down ~60% Down ~58%

Operating Profit(3)Margin

$6312%

$78 - $8514-15%

$79.0 - $85.014-15%

Unlevered Free Cash Flow(3)

Margin

$6412%

$84 - $9215-16%

$85.0 - $92.015-16%

32

Q3 2018 Actual Q3 2019 Guidance(1)

Total RevenueGrowth

$134 $141.0 - $143.05-7% / 7-8% CC

Subscription RevenueGrowth

$119 $135.0 - $137.014-15% / 15-17% CC

Professional Consulting Services Revenue $15 Down ~60%

Operating Profit(2)Margin

$1813%

Operating Margin in mid-teens

Unlevered Free Cash Flow(2)

Margin

$3224%

uFCF Margin in high single-digits

Q3 2019 Guidance

OTHER:1. GBP to USD 1.22

EUR to USD 1.12

2. Net Interest Expense(3):• GAAP $4• Non-GAAP $3

3. Shares outstanding increases from 60M to 66M when Net Income is positive

4. Capex is expected to comprise ~4% of revenue

(Dollar in millions)

Note:1. Reflects guidance issued as o August 5, 20192. Denotes a non-GAAP metric3. Net Interest Expense is Gross Interest Expense less Interest Income 33

Creating Long-Term Shareholder Value

Note: FY19 guidance updated as of August 5, 2019.

FY18Actual

FY19Guidance

2020 Balanced Growth/Profitability

Scenarios

Subscription Revenue Growth(in Constant Currency) 19% 16-17% 10 - 20%

Non-GAAP Operating Margin 12% 14-15% 18 - 28%

Unlevered Free Cash Flow Margin 12% 15-16% 20 - 30%

34

GAAP to Non-GAAP Reconciliation

35

36

Investment Summary

Organically-developed, best-of-breed SaaS platform

Huge, untapped market opportunity

Industry-leading customer retention

Highly scalable business

Top line growth with significant profitability improvement

A leader in cloud-based learning and human capital management

Transformation into a high-margin growth company

37

Thank You!