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Schedule

12:00 – 12:30 Welcome and CEO Update

Aaron Skonnard

12:30 – 1:00 CXO Platform Overview & Demo

Nate Walkingshaw

1:00 – 1:10 Break

1:15 – 1:45 CFO Financial Overview

James Budge

1:45 – 2:30 Q&A

Aaron Skonnard, James Budge, Nate Walkingshaw

Investor PresentationApril 2019

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Safe Harbor StatementThis presentation regarding Pluralsight, Inc. (“Pluralsight”, “we,” “us” or “our”) is strictly confidential and is for you to familiarize yourself with the company.

This presentation includes forward-looking statements within the meaning of Section27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange of 1934, as amended. All statements contained in this presentationother than statements of historical facts, including statements regarding future results of operations and financial condition of Pluralsight, our business strategy and plans and our objectives for future operations, are forward-looking statements.The words “anticipate,” “believe,” “continue,” “estimate,” “expect,” “intend,” “may,” “will” and similar expressions are intended to identify forward-looking statements. We have based these forward-looking statements largely on our currentexpectations 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, uncertainties and assumptions including the indicativeness of our historical financial results, our ability to manage and sustain our growth, our limited operating history, the successof our strategic relationships, our ability to grow internationally, competition in our industry, general economic trends and market risks, and other factors. Moreover, we operate in a competitive and rapidly changing environment in which new risksemerge 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 our actual results orperformance to differ materially from those contained in any forward-looking statements we may make. In light of these risks, uncertainties and assumptions, the future events and trends discussed in this presentation may not occur and actualresults could differ materially and adversely from those anticipated or implied in the forward-looking statements.

Although we believe that the expectations reflected in the forward-looking statements are reasonable, we cannot guarantee that the future results, levels of activity, performance, achievements or events and circumstances reflected in the forward-looking statements will occur. We are under no duty to update any of these forward-looking statements after the date of this presentation, except as required by law. You should, therefore, not rely on these forward-looking statements asrepresenting our views as of any date subsequent to the date of this presentation.

This presentation also contains estimates, projections and other statistical data made by independent parties and by us relating to market size and growth and other data about our industry and our business. This data involves a number ofassumptions and limitations, and you are cautioned not to give undue weight to such estimates. We have not independently verified the accuracy and completeness of the information obtained by third parties included in this presentation. Inaddition, 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 includes certain non-GAAP financial measures as defined by SEC rules. The non-GAAP financial measures have limitations as analytical tools and you should not consider them in isolation or as a substitute for the most directlycomparable financial measures prepared in accordance with GAAP. We urge you to review the reconciliation of our non-GAAP financial measures to the most directly comparable GAAP financial measures set forth in the Appendix to thispresentation, and not to rely on any single financial measure to evaluate our business.

Before you invest, you should read our documents filed with the SEC for more complete information about Pluralsight. You may get these documents for free by visiting EDGAR on the SEC website at www.sec.gov.

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1. Calculated by taking the number of global technical team members based on a study by Evans Data Corporation (2018) multiplied by our average billings per user as of December 31, 2018

2. As of March 31, 2019

$252M TTM REVENUE (2)

Cloud-based technology skills platform closing the global technology skills gap

85% OF TTM BILLINGS (2)

FROM BUSINESS CUSTOMERS

EXCEPTIONAL GROWTH RATES

Revenue and Billings growing @ 40%+17,200+ BUSINESS CUSTOMERS(2)

Helping enterprises adapt and thrive in the digital age

Enabling technologists to keep pace with change

Addressing $31 billion market opportunity(1)

Pluralsight Overview

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1. U.S. Department of Labor, Bureau of Labor Statistics

2. Source: Economic Intelligence Unit, The Quest for Digital Skills: A multi-industry executive survey (2016).

3. Source: ACT – The App Association, “State of the App Economy, Fifth Edition”

Past Present

Pace of Technological Change

Pace of Learning

94% of ExecutivesCite a Digital Skills Gap in Their Business(2)

Businesses Face a Massive Technology Skills Gap

>1,000,000 Open Computing Jobs in the U.S. by 2024(3)

>700 Notable Programming Languages Today

“Software Developers Must Redevelop Skills Every 12-18 Months”(1)

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Existing Solutions Fall Short on Delivering for Today’s Tech Professional

CLASSROOM

FREE Online Training

Unreliable content with no measurement of mastery

Not scalable, personalized or measurable

Static corporate mandated courses; mostly broad content

focus rather than laser focus on tech skills

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Large and Expanding Addressable Market

1. Source: Evans Data Corporation, Technical Team Total Addressable Market for Morgan Stanley (January 2018) (an estimate for 2017).

2. Source: Training Industry, Size of the Training Industry (April 2017) (an estimate of 2018 spend).

Analyst Estimated Market

$366Bn Global Corporate

Training(2)

Global corporate training shifting toward technology training

$31Bn102MM Global

Technical Team Members(1)

Today’s TAM

Penetration

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Evolution of Pluralsight

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As of March 31, 2018

Business AnalyticsSee the skills that exist in the organization and measure progress

Paths & Channels Align learning to key business objectives

Role IQDiscover the skills gaps holding team members back and fill them fast

Interactive CoursesPractice with hands-on coding

challenges and guided feedback

ProjectsApply learned skills to

real-world scenarios

Skill IQAssess skills in under

10 minutes and 20 questions

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Scott Allen is a nationally recognized

server-side and web expert

Deborah Kurata is a Microsoft MVP and Google

Developer Expert

Troy Hunt is a world-renown expert in cybersecurity and has testified in Congress as an expert witness

David Liu is a Salesforce Technical Architect at Google

and runs the largest installation of Salesforce in the

world

Delivering the Best Content Drives Continuous Platform Adoption

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UNPRECEDENTED VISIBILITY INTO SKILLS AND PRODUCTIVITYPLURALSIGHT + GITPRIME

MEASURE SKILLS IDENTIFY GAPS

DEVELOP SKILLSAPPLY SKILLS

With Skill and Role IQ tech leaders have unprecedented insights into the skill gaps across their orgs, our platform provides leaders the tools to close them

Technology teams can upskill efficiently with our platform;

allows leaders to future-proof their companies, avoid disruption

and advance innovation

With real-time visibility into the efficiency and performance of

developers, leaders can quickly identity bottlenecks and manage team performance through data-

centered discussion

GitPrime offers a view of every developer code commit; leaders get a clear and unbiased perspective of the application of skills in real-time

Holistic and targeted platform enabling tech leaders to successfully

execute and deliver their digital transformation

strategies

PLURALSIGHT + GITPRIME

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Why Customers Choose Pluralsight

1. Forrester, The Total Economic Impact of Pluralsight: Cost Savings and Business Benefits Enabled by Pluralsight (A Forrester Total Economic Impact Study Commissioned by Pluralsight) (October 2017). Data references are only with respect to customers in the study.

2. Average for the trailing twelve months ended 3/31/2019.

Skill assessments, course library, learning paths and analyticsINTEGRATED

High quality content tailored to individual needsPERSONALIZED

ROI of 295% over 3 yearsCOST EFFECTIVE(1)

Ability to access anytime, anywhere, from almost any deviceSCALABLE

Continuous training of technology skills for professionalsFOR PROFESSIONALS

CUSTOMER NPS OF 62(2)

Faster product developmentHigher employee retentionStreamlined new hire onboarding

RoleIQ, Objective Driven Channels, Interactive Courses and Projects. EXPANDING CAPABILITIES

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Our Customers Represent All Industries Across the Globe

1. As of December 31, 2018

70%+ of the 2018 Fortune 500(1) Users in over 180 countries(1)~2,400 net new customers added TTM

Financial Services Internet Technology Healthcare

Media & Entertainment Consumer Goods / Retail Transportation & Logistics Government Contractors

Manufacturing Energy Education Professional Services

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Product Offering Overview

SINGLE USERLicenses Include

Entire Course Library

Guided Learning Paths

Skill IQ

Role IQ

Channels

Course Discussions

Learning Checks

Exercise Files

Mobile + Offline Viewing

Completion Certificates

Support

$299/YR PERSONAL

$449/YR PREMIUM

SINGLE USERPremium Licenses Include

All PersonalFeatures Plus:

Interactive Courses

Projects

Certification Practice Exams

Licenses Include

$779/YR ENTERPRISE

Basic Skills Analytics

Basic Channels Analytics

Trend Analytics

Usage Analytics

Team Management

Single Sign-on (SSO)

Data Export

API Access

Advanced Channels Analytics

Advanced Skills Analytics

$579/YR PROFESSIONAL

Licenses Include

85% OF BILLINGS COME FROM BUSINESS CUSTOMERS (1)

1. For the twelve months ended March 31, 2019

All Premium Features Plus:

All Professional Features Plus:

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Efficient Strategy to Attract and Convert Long-Term Customers

Free Assessments

Individual Paid

Significant Majority Work at a Company

Business

ADOPTION FUNNEL

DIGITAL MARKETING/SELF-SERVICE

FIELD SALES

DIRECT SALES

Focused on New Business CustomersExpanding Usage and Upsell

Broad Distribution

~30%(2)

~70%(2)

1. For the twelve months ended March 31, 2019

2. % of revenue for the twelve months ended March 31, 2019, majority of top of funnel currently from Digital Marketing, but Partner lead generation is growing

3. Partners provide both lead generation and direct billing relationships

85%

PARTNERS(3)

PARTNERS(3)

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Significant Growth and Upside Opportunities

• Expand use cases

• Expand deployments• Expand course library

• Add features

• Add product tiers

• Expand sales force

• Expand sales teams in Europe and Asia-Pacific

EXPAND WITHIN EXISTING CUSTOMERS

GROW ENTERPRISECUSTOMER BASE

EXPANDGEOGRAPHICALLY

EXPAND OFFERING

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1. For the quarter ended March 31, 2019

2. Please refer to appendix for definition of dollar-based net retention rate

3. For the three month period ended March 31, 2019

Financial Highlights

Projecting $312M – $318M in revenue for FY 2019Significant Scale

48% business billings growth with 86% billings from business customers(1)High Growth

Growing importance within existing customers driving 128% dollar-based net retention rate(2)Retention & Expansion

77% Q1 2019 non-GAAP gross margin with demonstrated leverage from author fee structure(3)Operating Leverage

Investing for theLong Term

Third consecutive quarter of positive cash flow, projecting positive cash flow for FY 2019Cash Flow

Investment in GitPrime and related go to market enhances product and sales outlook, expediting our path to our target model

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Billings(1-3)

US$M

Revenue(1-3)

US$M

1. Business customer subscription terms typically range from 1 – 3 years

2. Individual customer subscription terms typically range from 1 month - 1 year

3. Substantial majority of business customers billed annually in advance

$132

$167

$232

$252

2016 2017 2018 TTM

27%Total YoY Growth (%): 39% 41%

Billings and Revenue on Significant Growth Paths

2016 2017 2018 TTM

Individuals Business Customers

70%

85%

$149

$206

$294

38% 43%Total YoY Growth (%):

B2B Billings YoY Growth (%):

55% 52%

$316

42%

51%

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Demonstrated Retention Improvement

1. Please refer to appendix for definition of dollar-based net retention rate

FY 2016

109%

Dollar-Based Net Retention Rate(1)

FY 2017

128%

117%

TTM

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1. See appendix for a reconciliation of GAAP Gross Profit to non-GAAP Gross Profit

Non-GAAP Gross Profit (1)

US$M

Non-GAAP Gross Profit

$98.3

$124.0

$177.2

$199.0

2016 2017 2018 TTM

75% 74%Non-GAAP Gross Margin (%):

76% 77%

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Business Customer Growth

Trailing 8 Quarters # of B2B Customers

12,580 13,214

13,887 14,463 14,830

15,507 16,185

16,756 17,213

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

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Increasing Volume of Large Deals

B2B Accounts with > $100K in Annual Billings

117

134

156

174

212

240

275

318

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

83% YoY growth

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2013 2017

Series 1Increase in Top 25 Customer BillingsBILLINGS INDEXED TO YEAR OF INITIAL PURCHASE 21x

Initial Purchase Year Annual Billings as of 3/31/2019

Demonstrated Ability to Execute on Land-and-Expand Model

1x

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1. 2019 guidance is forward-looking, is subject to significant business, economic, regulatory and competitive uncertainties and contingencies, many of which are beyond the control of the Company and its management, and are based upon assumptions with respect to future decisions, which are subject to change. Actual results will vary and those variations may be material. For discussion of some of the important factors that could cause these variations, please consult the “Risk Factors” section of the Annual Report on Form 10-K. Nothing in this presentation should be regarded as a representation by any person that these goals will be achieved and the Company undertakes no duty to update its goals.

2. Pluralsight has not reconciled its expectations as to adjusted pro forma net loss per share to their most directly comparable GAAP measures because certain items cannot be reasonably predicted. Accordingly, a reconciliation for expectations for adjusted pro forma net loss per share is not available without unreasonable effort.

FY’17 FY’18 FY’19

Revenue $167 $232 $312 - $318

Non-GAAP EPS n/a $0.60(2) $0.42 - $0.38(2)

2019 Guidance

Revenue, EPS (1)

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1. Each of the measures presented in this table are non-GAAP measures. See the appendix for a reconciliation of each measure to the most directly comparable GAAP measure. The Company has not provided a reconciliation of the forward-looking information presented in the Target Model because material items that impact that reconciliation are not reasonably estimable at this time.

2. Target model is forward-looking, is subject to significant business, economic, regulatory and competitive uncertainties and contingencies, many of which are beyond the control of the Company and its management, and are based upon assumptions with respect to future decisions, which are subject to change. Actual results will vary and those variations may be material. For discussion of some of the important factors that could cause these variations, please consult the “Risk Factors” section of the Annual Report on Form 10-K. Nothing in this presentation should be regarded as a representation by any person that these goals will be achieved and the Company undertakes no duty to update its goals.

FY’16 FY’17 FY’18 TTM TARGET MODEL(2)

GROSS MARGIN 75% 74% 76% 77% ~80%

TECHNOLOGY & CONTENT

25% 28% 24% 24% ~15%

SALES & MARKETING 37% 60% 60% 58% ~35%

GENERAL & ADMINISTRATIVE

12% 18% 16% 15% ~8%

OPERATING MARGIN 0% (31%) (23%) (22%) ~22%

Target Model

Non-GAAP Metrics (1)

% of Revenue

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Investment Highlights

1. As of March 31, 2019. Please refer to appendix for definition of dollar-based net retention rate

2. For the three-month period ended March 31, 2019. See appendix for a reconciliation of GAAP Gross Profit to non-GAAP Gross Profit

3. Estimate as of March 31, 2019

+51% TTM business billings growth with 85% billings from business customers

Sales & marketing investment supported by 128% retention rate(1)

Demonstrated sales productivity improvement

Addressing $31 billion market opportunity(3)

Technology and expert authors producing exceptional content, experiences and skills

Non-GAAP gross margin of 77% in Q1 2019(2)

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Thank you

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Appendix

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GAAP to Non-GAAP Reconciliation

$ Thousands 2016 2017 2018 3/31/2019 2016 2017 2018 2019

FY FY FY TTM Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1

GAAP Gross Profit 91,680 116,996 169,479 187,633 21,836 23,132 23,075 23,637 26,030 27,004 30,704 33,258 34,758 37,682 46,222 50,817 52,912

Equity-Based Compensation 20 20 140 219 5 5 5 5 5 5 5 5 - 46 40 54 79

Employer Payroll Taxes on Employee Stock Transactions - - 16 19 - - - - - - - - - - - 16 3

Amortization of Acquired Intangibles 6,565 7,008 7,586 5,149 1,643 1,640 1,640 1,642 1,642 1,642 1,642 2,082 2,962 2,961 880 783 525

Non-GAAP Gross Profit 98,265 124,024 177,221 193,020 23,484 24,777 24,720 25,284 27,677 28,651 32,351 35,345 37,720 40,689 47,142 51,670 53,519

Non-GAAP Gross Profit Margin (%) 75% 74% 76% 77% 75% 75% 74% 74% 74% 74% 75% 75% 76% 76% 77% 77% 77%

GAAP Operating Loss (13,843) (82,746) (118,513) (132,166) (3,923) (2,847) (828) (6,245) (8,268) (16,752) (30,248) (27,478) (19,326) (37,192) (29,795) (32,200) (32,979)

Equity-Based Compensation 5,738 21,781 54,303 70,536 808 1,373 1,250 2,307 1,712 4,379 12,897 2,793 3,373 17,555 16,044 17,331 19,606

Employer Payroll Taxes on Employee Stock Transactions - - 1,180 2,624 - - - - - - - - - - - 1,180 1,444

Amortization of Acquired Intangibles 8,034 8,526 8,681 6,050 2,013 2,011 2,004 2,006 2,006 2,006 2,006 2,508 3,333 3,332 1,056 960 702

Secondary Offering Costs - - - 918 - - - - - - - - - - - - 918

Non-GAAP Operating Profit / (Loss) (71) (52,439) (54,349) (52,038) (1,102) 537 2,426 (1,932) (4,550) (10,367) (15,345) (22,177) (12,620) (16,305) (12,695) (12,729) (10,309)

Non-GAAP Operating Profit / (Loss) Margin (%) (0%) (31%) (23%) (21%) (4%) 2% 7% (6%) (12%) (27%) (35%) (47%) (25%) (30%) (21%) (19%) (15%)

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GAAP to Non-GAAP Reconciliation (Cont’d)

$ Thousands 2016 2017 2018 3/31/19 2016 2017 2018 2019

FY FY FY TTM Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1

GAAP Sales and Marketing Expense 51,234 103,478 153,643 168,226 11,581 12,878 11,576 15,199 17,826 23,018 29,410 33,224 29,467 38,933 41,392 43,851 44,050

Equity-Based Compensation 1,462 2,624 14,330 19,986 246 261 317 638 664 715 631 614 539 4,432 4,372 4,987 6,195

Employer Payroll Taxes on Employee Stock Transactions - - 418 1,026 - - - - - - - - - - - 418 608

Amortization of Acquired Intangibles 643 721 389 194 160 161 161 161 161 161 161 238 195 194 - - -

Non-GAAP Sales and Marketing Expense 49,129 100,133 138,506 147,020 11,175 12,456 11,098 14,400 17,001 22,142 28,618 32,372 28,733 34,307 37,020 38,446 37,247

Non-GAAP Sales and Marketing Expense as a % of Revenue 37% 60% 60% 58% 36% 38% 33% 42% 46% 57% 66% 68% 58% 64% 60% 57% 54%

GAAP Technology and Content Expense 36,159 49,293 65,998 72,705 9,962 8,898 8,011 9,288 10,205 11,326 12,448 15,314 13,325 16,493 17,227 18,953 20,032

Equity-Based Compensation 2,050 1,966 8,747 11,864 379 479 487 705 464 526 499 477 381 2,668 2,790 2,908 3,498

Employer Payroll Taxes on Employee Stock Transactions - - 346 826 - - - - - - - - - - - 346 480

Amortization of Acquired Intangibles 706 706 706 707 177 176 176 177 176 176 176 178 176 177 176 177 177

Non-GAAP Technology and Content Expense 33,403 46,621 56,199 59,308 9,406 8,243 7,348 8,406 9,565 10,624 11,773 14,659 12,768 13,648 14,261 15,522 15,877

Non-GAAP Technology and Content Expense as a % of Revenue 25% 28% 24% 24% 30% 25% 22% 25% 26% 27% 27% 31% 26% 25% 23% 23% 23%

GAAP General and Administrative Expense 18,130 46,971 68,351 78,868 4,216 4,203 4,316 5,395 6,267 9,412 19,094 12,198 11,292 19,448 17,398 20,213 21,809

Equity-Based Compensation 2,206 17,171 31,086 38,467 178 628 441 959 579 3,133 11,762 1,697 2,453 10,409 8,842 9,382 9,834

Employer Payroll Taxes on Employee Stock Transactions - - 400 753 - - - - - - - - - - - 400 353

Amortization of Acquired Intangibles 120 91 - - 33 34 27 26 27 27 27 10 - - - - -

Secondary Offering Costs - - - 918 - - - - - - - - - - - - 918

Non-GAAP General and Administrative Expense 15,804 29,709 36,865 38,730 4,005 3,541 3,848 4,410 5,661 6,252 7,305 10,491 8,839 9,039 8,556 10,431 10,704

Non-GAAP General and Administrative Expense as a % of Revenue 12% 18% 16% 15% 13% 11% 12% 13% 15% 16% 17% 22% 18% 17% 14% 16% 15%

Total Non-GAAP Operating Expense 98,336 176,463 231,570 245,058 24,586 24,240 22,294 27,216 32,227 39,018 47,696 57,522 50,340 56,994 59,837 64,399 63,828

Non-GAAP Operating Expense as a % of Revenue 75% 106% 100% 97% 78% 73% 67% 79% 87% 100% 110% 121% 101% 106% 97% 96% 92%

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DEFINITION

Dollar-based net retention rate

To calculate our dollar-based net retention rate, we first calculate the subscription revenue in one quarter from a cohort of customers that were customers at the beginning of the same quarter in the prior fiscal year, or cohort

customers. We repeat this calculation for each quarter in the trailing four-quarter period. The numerator for dollar-based net retention rate is the sum of subscription revenue from cohort customers for the four most recent

quarters, or numerator period, and the denominator is the sum of subscription revenue from cohort customers for the four quarters preceding the numerator period. Dollar-based net retention rate is the quotient obtained by

dividing the numerator by the denominator.

GAAP to Non-GAAP Reconciliation (Cont’d)

$ Thousands 2016 2017 2018 2019 2018 2019

FY FY FY TTM Q1 Q1

Net cash provided by (used in) operating activities 4,468 (12,139) (5,896) 10,068 (10,424) 5,540

Less: purchases of property and equipment 10,142 5,951 8,796 9,061 1,868 2,133

Less: purchases of content library 2,253 2,382 3,340 3,508 769 937

Free Cash Flow (7,927) (20,472) (18,032) (2,501) (13,061) 2,470

Free Cash Flow Margin (%) (6%) (12%) (8%) (1%) (26%) 4%