Pluralsight Investor Presentation

Investor Presentation 1

Safe Harbor Statement 2

Pluralsight Overview Cloud-based technology skills platform closing the global technology skills gap Helping enterprises adapt and thrive in the digital age Enabling technologists to keep pace with change Addressing $42 billion market opportunity(1) $400M TTM BILLINGS(2) 88% OF TTM BILLINGS(2) ~1.43M BUSINESS USERS(2) FROM BUSINESS CUSTOMERS 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, 2019. $31B of TAM for Pluralsight Skills, $11B of TAM for Pluralsight Flow. 2. As of June 30, 2020 3

Businesses Face a Massive Technology Skills Gap Pace of Technological Change 87% of Tech Executives Cite the challenge of finding skilled tech “Software Developers Must Redevelop Skills Every 12-18 Months”(1) talent(2) 700,000 unfilled tech jobs in the US(3) 3,700,000tech job postings during 2018(3) 2x median tech wage is double the median national wage (3) Pace of Learning Past Present 1. Deloitte Global Human Capital Trends 2. Source: The State of US Tech Hiring – Robert Half Q1/Q2 2019 3. Source: ACT –CompTIA –Cyberstates 2019 4

Existing Solutions Fall Short on Delivering for Today’s Tech Professional CLASSROOM FREE Online Training Static corporate mandated Unreliable content with no courses; mostly broad content measurement of mastery Not scalable, focus rather than laser focus on personalized or measurable tech skills 5

Large and Expanding Addressable Market Today’s TAM Analyst Estimated Market $42Bn 102MMGlobal Technical Team Members(1) Global corporate training shifting toward >$300Bn Penetration technology training by 2025 Global eLearning Market Size(2) 1. Source: Evans Data Corporation, Technical Team Total Addressable Market for Morgan Stanley (January 2018) (an estimate for 2017). $31B of TAM for Pluralsight Skills, $11B of TAM for Pluralsight Flow. 2. Source: Global Market Insights, Global eLearning Market Size worth over $300bn by 2025 (https://www.gminsights.com/pressrelease/elearning-market). 6

Evolution of Pluralsight 7

Skill IQ Role IQ Assess skills in under Discover the skills gaps holding 10 minutes and 20 questions team members back and fill them fast Projects Paths & Channels Apply learned skills to Align learning to key real-world scenarios business objectives Interactive Courses Business Analytics Practice with hands-on coding See the skills that exist in the challenges and guided feedback organization and measure progress As of March 31, 2018 8

UNPRECEDENTED VISIBILITY INTO SKILLS AND PRODUCTIVITY SKILLS + FLOW MEASURE SKILLS IDENTIFY GAPS With Skill and Role IQ tech With real-time visibility into the leaders have unprecedented efficiency and performance of insights into the skill gaps across developers, leaders can quickly their orgs, our platform provides SKILLS + FLOW identity bottlenecks and manage leaders the tools to close them team performance through data- Holistic and targeted centered discussion platform enabling tech leaders to successfully execute and deliver their APPLY SKILLS digital transformation DEVELOP SKILLS Flow offers a view of every strategies Technology teams can upskill developer code commit; leaders get efficiently with our platform; a clear and unbiased perspective of allows leaders to future-proof the application of skills in real-time their companies, avoid disruption and advance innovation 9

Why Customers Choose Pluralsight INTEGRATED Skill assessments, course library, learning paths and analytics PERSONALIZED High quality content tailored to individual needs Faster product development COST EFFECTIVE(1) ROI of 295% over 3 years Higher employee retention Streamlined new hire onboarding SCALABLE Ability to access anytime, anywhere, from almost any device FOR PROFESSIONALS Continuous training of technology skills for professionals EXPANDING CAPABILITIES Developer Productivity, Interactive Courses and Projects CUSTOMER NPS OF 62(2) 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 6/30/2020. 10

Efficient Strategy to Attract and Convert Long-Term Customers ADOPTION FUNNEL Free Assessments PARTNERS(2) DIGITAL MARKETING/SELF-SERVICE Individual Paid Significant Majority Work at a Company Business Focused on New Business Customers Expanding Usage and Upsell Broad Distribution PARTNERS(2) 88% 1. For the twelve months ended June 30, 2020 2. Partners provide both lead generation and direct billing relationships 11

Our Customers Represent All Industries Across the Globe 70% of the 2020 Fortune 500(1) ~18,000 B2B Customers(1) Users in over 180 countries(1) Financial Services Internet Technology Healthcare / Pharma Media & Entertainment Consumer Goods / Retail Transportation & Logistics Government Contractors Manufacturing Energy Insurance Professional Services 1. As of June 30, 2020 12

Significant Growth and Upside Opportunities EXPAND GEOGRAPHICALLY GROW ENTERPRISE CUSTOMER BASE EXPAND WITHIN EXISTING • Expand sales teams in EXPAND OFFERING CUSTOMERS Europe and Asia-Pacific • Expand sales force • Expand use cases • Expand course library • Expand deployments • Add features • Add product tiers 13

Financial Highlights Significant Scale Projecting $375 –$390M in revenue for FY 2020 Retention & (1) Expansion Growing importance within existing customers driving 118%dollar-based net retention rate (2) Operating Leverage 81% Q2 2020 non-GAAP gross margin with demonstrated leverage from author fee structure Investing for the Investment in Pluralsight Flow and related go to market enhances product and sales outlook, Long Term expediting our path to our target model Exited Q2’20 with $550M+ in total Cash and Investments Cash & Cash Flow History of positive cash flow (2004 through 2015 and Q3-Q4 2018, Q1 2019, Q1 2020) $9M in Operating Cash Flow in 1H 2020, and neutral Free Cash in 1H 2020 (excl. cash spent on new campus) 1. Please refer to appendix for definition of dollar-based net retention rate 2. For the three-month period ended June 30, 2020 14

Billings and Revenue Growth (1-3) (1-3) Billings Revenue US$M US$M Total YoY Growth (%): 43% 29% 21% Total YoY Growth (%): 39% 37% 31% B2B Billings 52% 33% 24% $359 YoYGrowth (%): $379 $400 $317 $294 $232 $206 88% $167 79% 2017 2018 2019 TTM 2017 2018 2019 TTM Individuals Business Customers 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 15

Demonstrated Strong Retention Dollar-Based Net Retention Rate(1) 118% 109% FY 2016 TTM 1. Please refer to appendix for definition of dollar-based net retention rate 16

Non-GAAP Gross Profit Non-GAAP Gross Profit (1) US$M Non-GAAP Gross 74% 76% 79% 81% Margin (%): $289 $250 $177 $124 2017 2018 2019 TTM 1. See appendix for a reconciliation of GAAP Gross Profit to non-GAAP Gross Profit 17

Increasing Volume of Large Deals B2B Accounts with > $100K, > $500K, and > $1M in Annual Billings $1M+ Customers 54% CAGR $500K+ Customers $100K+ Customers 80% CAGR 118% CAGR 2017 2018 2019 Q2'20 18

2020 Guidance Revenue, EPS (1) FY’18 - Actual FY’19 - Actual FY’20 - Guidance Revenue $232M $317M $375 - $390M (2) (2) (2) Non-GAAP EPS ($0.60) ($0.30) ($0.27) – ($0.19) Cash Flow Positive in Q4 2020 1. 2020 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. 19

Target Model Non-GAAP Metrics (1) % of Revenue TARGET MODEL FY’17 FY’18 FY’19 Q2’20 Based on Rev of $1B(2) GROSS MARGIN 74% 76% 79% 81% ~80% TECHNOLOGY & 28% 24% 25% 23% ~15% CONTENT SALES & MARKETING 60% 60% 55% 49% ~35% GENERAL & 18% 16% 14% 14% ~8% ADMINISTRATIVE OPERATING MARGIN (31%) (23%) (16%) (5%) ~22% 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. 20

Investment Highlights 24% TTM YoY business billings growth with 88% billings from business customers(1) Sales & marketing investment supported by 118% retention rate(1) Non-GAAP gross margin of 81% in Q2 2020(2) Addressing $42 billion market opportunity(3) History of positive cash flows and $550M+ of cash and investments 1. TTM As of June 30, 2020. Please refer to appendix for definition of dollar-based net retention rate 2. For the three-month period ended March 31, 2020. See appendix for a reconciliation of GAAP Gross Profit to non-GAAP Gross Profit 3. 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. $31B of TAM for Pluralsight Skills, $11B of TAM for Pluralsight Flow. 21

Appendix 22

GAAP to Non-GAAP Reconciliation $ Thousands 2020 Q2 2019 Q2 2018 Q2 2020 2019 TTM TTM TTM Q2 Q2 GAAP Gross Profit 283,279 207,981 136,359 75,048 58,059 Equity-Based Compensation 897 333 99 296 133 Employer Payroll Taxes on Employee Stock Transactions 39 32 - 15 13 Amortization of Acquired Intangibles 4,836 2,890 9,647 1,209 702 Non-GAAP Gross Profit 289,051 211,236 146,105 76,568 58,907 Non-GAAP Gross Profit Margin (%) 81% 77% 75% 81% 78% GAAP Operating Loss (156,394) (139,869) (125,668) (35,221) (37,381) Equity-Based Compensation 99,440 83,140 48,042 26,425 22,732 Employer Payroll Taxes on Employee Stock Transactions 3,030 3,953 - 997 1,329 Amortization of Acquired Intangibles 5,725 3,625 11,179 1,420 907 Secondary Offering Costs 1,260 918 - 1,260 - Acquisition Related Costs - 835 - - 835 Non-GAAP Operating Profit / (Loss) (46,939) (47,398) (66,447) (5,119) (11,578) Non-GAAP Operating Profit / (Loss) Margin (%) (13%) (17%) (34%) (5%) (15%) 23

GAAP to Non-GAAP Reconciliation (Cont’d) $ Thousands 2020 Q2 2019 Q2 2018 Q2 2020 2019 TTM TTM TTM Q2 Q2 GAAP Sales and Marketing Expense 233,042 181,302 133,958 57,759 50,046 Equity-Based Compensation 36,849 25,429 9,140 10,878 7,952 Employer Payroll Taxes on Employee Stock Transactions 973 1,559 - 329 533 Amortization of Acquired Intangibles 200 29 788 50 29 Non-GAAP Sales and Marketing Expense 195,020 154,285 124,030 46,502 41,532 Non-GAAP Sales and Marketing Expense as a % of Revenue 54% 56% 64% 49% 55% GAAP Technology and Content Expense 117,470 82,658 59,483 29,514 24,819 Equity-Based Compensation 25,803 15,933 5,928 6,884 5,137 Employer Payroll Taxes on Employee Stock Transactions 1,011 1,260 - 381 434 Amortization of Acquired Intangibles 689 706 707 161 176 Non-GAAP Technology and Content Expense 89,967 64,759 52,848 22,088 19,072 Non-GAAP Technology and Content Expense as a % of Revenue 25% 24% 27% 23% 25% GAAP General and Administrative Expense 89,161 83,890 68,586 22,996 20,575 Equity-Based Compensation 35,891 41,445 32,875 8,367 9,510 Employer Payroll Taxes on Employee Stock Transactions 1,007 1,102 - 272 349 Amortization of Acquired Intangibles - - 37 - - Secondary Offering Costs 1,260 918 - 1,260 - Acquisition Related Costs - 835 - - 835 Non-GAAP General and Administrative Expense 51,003 39,590 35,674 13,097 9,881 Non-GAAP General and Administrative Expense as a % of Revenue 14% 14% 18% 14% 13% Total Non-GAAP Operating Expense 335,990 258,634 212,552 81,687 70,485 Non-GAAP Operating Expense as a % of Revenue 94% 94% 110% 86% 93% 24

GAAP to Non-GAAP Reconciliation (Cont’d) $ Thousands 2020 Q2 2019 Q2 2018 Q2 2020 2019 TTM TTM TTM Q2 Q2 Net cash provided by (used in) operating activities (1,036) 8,673 (24,406) (9,250) (7,184) Less: purchases of property and equipment (27,111) (8,812) (7,500) (6,626) (2,457) Less: purchases of content library (6,678) (4,277) (2,657) (2,113) (1,504) Free Cash Flow (34,825) (4,416) (34,563) (17,989) (11,145) Free Cash Flow Margin (%) (10%) (2%) (18%) (19%) (15%) 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. 25