NASDAQ: CSOD

June 4, 2019

2019 Investor/ Analyst Day

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 di ffer 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 serv ice 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 solut ions, 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 effecti ve 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 fil ed 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

Agenda

• Welcome – Jason Gold, VP of Finance and Corporate Development

• Strategic Review – Adam Miller, Founder & CEO

• Exec Interviews – Heidi Spirgi, Mark Goldin and Jeff Lautenbach

• Partner Panel – Deloitte and Alight

• Content Panel – Whil, TED, and Service King

• Financial Overview – Brian Swartz, Chief Financial Officer

3

Adam MillerFounder & CEO

4

Looking Back: The Transformation

5

Focus on recurring revenue and exit enterprise

service delivery

Improve operating margins and cash flows

Create new recurring revenue streams and

aggressively enter the content market

Bolster the team

Improve governance

Transforming Cornerstone

1

2

3

4

5

6

Focus on recurring revenue and exit enterprise

service delivery

Improve operating margins and cash flows

Create new recurring revenue streams and

aggressively enter the content market

Bolster the team

Improve governance

Transforming Cornerstone

✓

✓

✓

✓

✓

7

Key Metrics: The Cornerstone Transformation

$439

$510

$578 - $590

2017 2018 2019E

Annual Recurring Revenue (ARR)

Not e: FY19 Guidance ranges as of M ay 7, 2019.

$482 $538 $562 - $570

2017 2018 2019E

Total Revenue

$397

$473

$537 - $545

2017 2018 2019E

Subscription Revenue

(in millions)

8Not e: A reconciliat ion of non-GAAP met rics used in this presentation to their nearest GAAP equivalent s is provided in t he appendix t o t his presentation.1 – Operat ing CF margin is calculat ed by dividing operat ing cash flow int o total revenue.

-10%

6%

12%14-15%

2017 2018 2019E

Operating Margin

GAAP OM Non-GAAP OM

-1%

14%17%

9%

12%

15-16%

2017 2018 2019E

Cashflow Margin

Operating CF Margin uFCF Margin1

Cornerstone Today

9

Global ReachCLIENTS

3,500+USERS

40M+COUNTRIES

190+LANGUAGES

43OFFICES

22

Sunnyvale

Santa Monica

Sao Paulo

Madrid

Paris

London

Stockholm

DusseldorfMunich

Tel Av iv

Bangalore

Mumbai

Hong 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 March 31, 2019

Salt Lake

City

New York

City San Francisco

Mexico City

10

Marquee Clients Around the WorldAPJUS & LATAM EMEA

11

COMPLETENESS OF VISION

AB

ILIT

Y T

O E

XEC

UTE

CHALLENGERS LEADERS

NICHE PLAYERS VISIONARIES

Cornerstone is the Market Leaderin Talent Management

SOURCE: Gartner 2018 Magic Quadrant for Talent Management Suites(September 2018)

2018 Magic Quadrant for Talent Management Suites

Cegid

Saba (TalentSpace)

Skillsoft (SumTotal Systems)

Saba (Saba Cloud)

Haufe

SAP (SuccessFactors)

Talentsoft

PageUp

12

The Macro Backdrop

13

The

Sk

ills Div

ide

is Re

al

Unskilled Labor

Unskilled JobsSkilled Jobs

Skilled Workers

Recruiters Are Overwhelmed

Average Number

Per Recruiter

40Submitted for the Average

Unskilled Job

250Requisitions Resumes

Many of the 6.5M Americans Looking for Work Today Do Not Possess the Skills Required to Do Most of the 7.6M Unfilled Jobs

Americans Looking for Work

Unfilled Jobs Requiring Skills

6.5M

7.6M

New jobs to be added

557,100

Average number of Computer and information technology graduates per year

40,000

Computer and Information Technology Occupation Projected Growth to 2026

Only 6% of all degrees earned each year are in computer and information technology

Skills Have Become

the New Digital Currency

18

How people consume video

How people consume audio

At the Same Time, Consumer Habits Have Changed

19

Expanding our Moat

20

Modern learning requires a holistic strategy

LearningExperience

(LXP)

LearningManagement

(LMS)

Modern Content

Cornerstone Learning

21

22

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

State of the Art Learning Experience

Highly Curated Collections of Content

Wide Partner Ecosystem

with a variety of modalities,

topics, and titles

Intelligently Curated

Subscriptionsbuilt 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

SubscriptionsIntegrated

with LXP

Content

ConsultantsBest-of-breed

Partners

24

Our Holistic Solution will Distance us from the Competition

25

26

Cornerstone's Second Act:$40 Billion Market Opportunity

$3.6B$6B

$16

$25

Founding to IPO IPO to 2017 2018

Learning Systems Market Full Talent Management HCM Content

~$40B

2018 and Beyond:

Cornerstone Operates in Two Markets

20-Year Start up

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

Global Corporate Training

$374b

External Training

$100b

Content

$77b

Our Content Topics

$50b

The Global Training Market is Huge

27Source: Training Industry EstimatesOnline Only

$25b

Our Opportunity is Enormous

Learning

520M+2018 Registrations

330M+2018Completions

Online Classes Only

28

With >4,500 Content Producers in North America Alone, the Content Market is Highly Fragmented

29

We Leverage our Massive Set of Aggregated and Anonymized Training Data to Curate

30

We Can See Which Countries Consume Content

31

And What Verticals Consume Content

32

And Which Providers are Popular

33

Data + Content + Scale = Cornerstone is Unique

Right Training

Right Person

Right Time

35

Everybody Wins

• Pre-curated content

• Holistic end-to-end

solution

Content Consumers

• Expanded distribution

• Incremental profit

Content Providers

• More at-bats

• Higher batting average

• More software revenue

Cornerstone

Jo Rossouw, Head of Digital Learning

36

Recruiting

37

Modern Recruiting Requires a Modern Solution

38

Recruiting GrowthThere is growing adoption of the Recruiting Suite

~ 300

~ 500

~ 600

~ 700

~ 800

2014 2015 2016 2017 2018

Recruiting Clients

39

Beyond Learning: Other Incremental Growth Drivers

40

Clear Opportunity to Further Penetrate the Installed Base

41

63%of clients with Learning

& Performancehave not

purchased Recruiting

3,567CSOD Clients

As of 3/31/2019

77%of clients

have not purchased Recruiting

22%of clients with CHR

have not purchased Recruiting

50% penetration in recruiting could drive an incremental $100M in ARR

Asia-Pacific & Japan

Focused on Fewer Markets

43

In mid-2018 we shifted to a more focused go-to-market approach across the APJ region, resulting in deeper levels of investment across fewer major markets

Australia & New Zealand Japan Asia

Singapore (ASEAN)

Hong Kong

South Korea

Increased Localization

44

Due to the differences across APJ markets, we also moved to a more localized approach in mid-2018, appointing leaders who have end-to-end responsibility for our growth in each individual APJ market

Managing Director

Sales Marketing Alliances Client Success

Immediate Results After Changes and Building Momentum

45

Growth in APJ had become stagnant, but after increasing our focus and taking a more localized approach in mid-2018 the results were immediate and momentum is building

40%

51%

0%

15%

30%

45%

60%

TTM June '18 2H '18 1H '19

0%

actual actual estimated

Key GTM Changes

Implemented

Increased

Investment

YoY ARR Growth

Highly Attractive Opportunity in Japan Remains Untapped

46

Large Market Size: Japan is the third-largest economy in the world behind the U.S. and China.

Attractive Market Profile: With more Fortune 2,000 companies than any nation except the U.S., a

significant portion of the Japan market falls in the Enterprise segment where our product has a strong

competitive advantage.

Multiple Precedent SaaS Success Stories: Enterprise cloud adoption is becoming more common in Japan, resulting in numerous SaaS success stories including the following:

$1B+ in ARR and1,300 Employees

$60M+ in ARR In 5 Years

$35M+ in ARR in 3 Years

1 Source: Company estimates

111

Small & Medium Business

Key GTM Changes Made in Mid-2017

48

A number of key go-to-market changes were made in mid-2017 to help us better address the SMB opportunity, resulting in sales productivity improving by more than four times versus the prior year

1.8x

4.3x

0.0x

1.0x

2.0x

3.0x

4.0x

5.0x

1H '17 2H '17

Key GTM Changes

Implemented

YoY Average Sales Productivity Improvement Per Rep

Accelerating Growth in 2019

49

57%

79%

0%

20%

40%

60%

80%

100%

'18 1H '19

After a full year of continued success in 2018 we elected to significantly increase our SMB investment heading into 2019, and as a result, year-over-year growth is accelerating

actual estimated

YoY ARR Growth

Highly Efficient Sales Approach

50

As we continue to grow aggressively down market, we are doing so more cost effectively with inside sales

BUSINESS DEVELOPMENT

RESOURCES

SOLUTION CONSULTANTS

RFP SUPPORT TRAVEL

Questions?

51

Panel Discussions

52

Executive Interviews

53

Jeff Lautenbach

President,

Global Field Operations

Heidi Spirgi

Chief Marketing

& Strategy Officer

Mark Goldin

Chief Technology Officer

Partner Panel

54

President of Global Field Operations

Jeff Lautenbach

MODERATOR

Senior Manager

Jason Magill

Vice President

Ernie Cambareri

Content Panel

55

Director, Learning & Development

Rachel Blackman

Vice President, Content Services

Josh Schwede

Founder & CEO

Joe Burton

Director, Global Distribut ion & Licensing

Alex Hofman

Vice President, Finance & Corporate Development

Jason Gold

MODERATOR

Brian SwartzChief Financial Officer

56

57

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

12% GROWTH

HCM – $16B 10%GROWTH

58

Content Economics

Content Subscription Margins

Content

Gross Revenue

50%

50% CSOD

Content

Providers

25%+OPERATING

MARGIN

59

Revenue Growth - Subscription vs. Services

$83 $85 $65 $25

$340

$397

$473

$0

$100

$200

$300

$400

$500

$600

2016 2017 2018 2019E

Subscription Revenue Growth vs. Total Revenue Growth

Subscription Revenue

$562-$570

$537-$545

(in millions)

$423

$482

$538

ServicesReflects guidance giv en May 7, 2019

60

Quarterly Services Revenue Trend (on purpose)

(in millions)

$18.7 $20.2 $20.7

$25.7

$20.0 $17.7

$15.2

$11.9

$8.9

$-

$5.0

$10.0

$15.0

$20.0

$25.0

$30.0

Q1 '17 Q2 '17 Q3 '17 Q4 '17 Q1 '18 Q2 '18 Q3 '18 Q4 '18 Q1 '19

61

Quarterly Subscription Revenue Growth(in millions)

$92.9 $96.4

$101.1 $106.3

$113.1 $114.8 $118.8

$126.3 $131.3

0%

5%

10%

15%

20%

25%

$-

$20

$40

$60

$80

$100

$120

$140

Q1 '17 Q2 '17 Q3 '17 Q4 '17 Q1 '18 Q2 '18 Q3 '18 Q4 '18 Q1 '19

Subscription Revenue YOY Growth - Subscription YOY Growth - Subscription CC

Note: Bar sizes are representative only and should not be used to estimate actual values

Starting ARR Currency ARR Churn New ARR fromExisting Customers

New ARR from NewCustomers

Ending ARR

How ARR MovesIllustrative Year-over-Year Bridge

62

63

How ARR Impacts Subscription Revenue

EXAMPLE: $1M DEAL

Jan 1 July 1 Dec 30

ARR = $1M

Full Yr Rev = $1M

ARR = $1M

Full Yr Rev = $0.5M

ARR = $1M

Full Yr Rev = $5K

64

Improving Operating Leverage

-14%

-5% -4% -4%

2%

6%

12%

14% - 15%

2012 2013 2014 2015 2016 2017 2018 2019E

Non-GAAP Operating Margin

$78M - $85M

1 Reflects guidance giv en May 7, 2019. A reconciliation of non-GAAP metrics used in this presentation to their nearest GAAP equivalents is prov ided in the appendix to this presentation

1

65

Improving Operating Leverage

3%2%

6%5%

4%

9%

12%

15% - 16%

2012 2013 2014 2015 2016 2017 2018 2019E

Unlevered Free Cash Flow $84M - $92M

1 Reflects guidance giv en May 7, 2019. A reconciliation of non-GAAP metrics used in this presentation to their nearest GAAP equivalents is prov ided in the appendix to this presentation

1

UNLEVERED FCF

Operating Cash flow

Capitalized Software

and Capex

Cash Interest

Unlevered Free

Cash Flow

-

+

Normalized 2019 uFCF

66

15-16%Margin

17-18%Margin

~1%

~1%

(in millions)

67

Operational Excellence Initiatives

1. Optimize S&M to improve productivity

2. Allocate new hires to lower-cost offices

3. Increase back-office automation

4. Optimize partner management

5. Migrate to the public cloud

6. Continue shift to recurring revenue

2018 Actual 2019 Guidance(1)

ARR(1)

Growth$510 $578 - $590

13-16% / 14-16% CC

Total RevenueGrowth

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

Subscription RevenueGrowth

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

Professional Services

Revenue$65 Down ~60%

Non-GAAP Operating

Profit(2)

Margin

$6312%

$78 - $8514-15%

Unlevered

Free Cash Flow(2)

Margin

$6412%

$84 - $9215-16%

2019 Guidance

OTHER:1. GBP to USD 1.32

EUR to USD 1.12

2. 5% FX Δ = $5 ARR / $6 Revenue

3. Net Interest Expense(3):• GAAP $15• Non-GAAP $11

4. Cash Interest Paid $17

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

posit ive

6. Income tax expense $3M

7. SBC as % of revenue ~13%, versus

prior year of 11%

8. Capex ~4% of revenue

(Dollars in millions)

Notes:

1. Reflects guidance issued as of May 7, 2019.2. Denotes a non-GAAP metric3. Net Interest Expense is Gross Interest Expense less Interest Income 68

A reconciliation of non-GAAP metrics used in this presentation to their nearest GAAP equiv alents is prov ided in the appendix to this presentation

Q2 2018 Actual Q2 2019 Guidance(1)

Total RevenueGrowth

$133 $137 - $1403-6% / 5-7% CC

Subscription RevenueGrowth

$115 $131 - $13314-16% / 15-17% CC

Professional Consulting

Services Revenue$18 Down ~60%

Non- GAAP Operating

Profit(2)

Margin

$1310%

Operating Margin in low

double-digits

Unlevered Free Cash Flow(2)

Margin

$86%

uFCF Margin in mid

single-digits

Q2 2019 Guidance

OTHER:1. GBP to USD 1.32

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 posit ive

4. Capex primarily in 1H for tenant improvement build-

outs

(Dollars in millions)

Note:

1. Reflects guidance issued as of May 7, 20192. Denotes a non-GAAP metric3. Net Interest Expense is Gross Interest Expense less Interest Income

69

A reconciliation of non-GAAP metrics used in this presentation to their nearest GAAP equiv alents is prov ided in the appendix to this presentation

2020 Growth vs Profitability Framework

Note: FY19 guidance updated as of May 7, 2019. A reconciliation of non-GAAP metrics used in this presentation to their nearest GAAP equivalents is provided in the appendix to this presentation 70

2020 Framework

FY18Actual

FY19Guidance

LowGrowth

Moderate Growth

HighGrowth

Subscription Revenue

Growth19% 14-15% < 10% 10 - 20% 21 - 30%

Non-GAAP Operating

Margin 12% 14-15% 30%+ 18 - 28% 12 - 22%

Unlevered Free Cash

Flow Margin12% 15-16% 30%+ 20 - 30% 15 - 25%

2020 ‘Moderate Growth’ Target Assumes ~$150M in uFCF and ~$2.00 Per Share

71

2020 and Beyond

Targeting rule of 40 in 2020

…but it’s not our final

destination. We see a path to

the mid-40s in the coming years.

Questions?

72

Thank You!

Appendix

74

75

76