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Forward-Looking Statements and Non-GAAP Measures

This presentation and oral statements made in connection with this presentation contain certain statements that are not historical facts, including information regarding our intentions, beliefs or current expectations concerning, among other things, our results of operations, including billings and net sales; financial performance and condition; liquidity; products and services, including for new adoptions; outlook for full year 2018; prospects; growth; markets and market share; strategies, including with respect to investing in our core solutions and extensions businesses and operational excellence; efficiency and cost savings initiatives; the industry in which we operate; and potential business decisions. Those statements constitute “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995. Forward-looking statements involve known and unknown risks, uncertainties and other factors that could cause our actual results to differ materially from the results express in or implied by our forward-looking statements, including, but not limited to, those identified under the caption “Forward-Looking Statements” in our news release issued on August 2, 2018 and in the “Special Note Regarding Forward-Looking Statements” and “Risk Factors” in our most recent Annual Report on Form 10-K and Quarterly Reports on Form 10-Q. We undertake no obligation, and do not expect, to publicly update or revise any forward-looking statement, whether as a result of new information, future events or otherwise. In addition, this presentation and oral statements made in connection with this presentation reference non-GAAP financial measures, such as adjusted EBITDA and free cash flow, and operating measures, such as billings. The use of these non-GAAP measures are limited as they include and/or do not include certain items not included and/or included in the most directly comparable GAAP measure. A reconciliation of non-GAAP financial measures to the most directly comparable GAAP financial measures (to the extent available without unreasonable efforts) and a calculation of operating measures are provided in the appendix to this presentation and in our news release issued on August 2, 2018, which are posted on hmhco.com under the Investor Relations section.

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Market Opportunity & Strategy

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Trade

13%

Extensions

45%

The HMH Business

Sources: 2017 HMH Billings Mix

Intervention Professional Learning Supplemental

Core Solutions

42%

13,000 Districts 88,000 Schools 50,000,000 Students 3,000,000 Teachers

650 Sales Representatives 42,000 Service Engagements

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Core Solutions Intervention

Classrooms consist of students with diverse academic ability, requiring different instructional needs

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English language development Professional Services Supplemental

Riverside Divestiture: Overview

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• HMH to sell Riverside Clinical and Standardized Testing to Alpine Investors for $140 million in cash
• Riverside Portfolio was non-core to our 2020 strategy
• Divestiture sharpens focus and creates opportunity to accelerate investment in faster growing, high

margin Extensions

• Riverside generated Billings of approximately $80 million in 2017
• Approximately $135 million of net proceeds expected to be re-deployed in faster growing, high

margin Extensions opportunities

• Year-to-date results and full year guidance will be adjusted to reflect the divestiture by the Q3 2018

earnings call

U.S. K–12 Market: Instructional Materials Spend

Instructional Materials Spend 2017 HMH Education Billings 2017 HMH International & Trade Billings Total 2017 HMH Billings

$1.2B $.2B $1.4B $11B

Basal Curriculum Services Assessment State Level Tests Courseware Digital Supplements Print Supplements Manipulative Magazines Trade Books Video

Sources: 2017 HMH Billings

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Sources: Simba, Company Annual Reports, SEC, Oliver Wyman November 2014 Intervention Web Survey, Oliver Wyman analysis, RAND Corporation School Leadership Interventions Under ESSA report; as of 2017.

Supplemental $2.0b Intervention $1.5b Professional Learning $2.3b

$6B

4% Growth 4% Growth 3% Growth

HMH Extensions: Market Opportunity

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From K12 Publisher to Learning Company

HMH Strategy: Three Pillars

Enhance & Extend the Core Develop Integrated Solutions Achieve Operational Excellence

• Provide highly differentiated products

that leverage data analytics and learning science to personalize learning

• Expand into faster growing, higher

margin extensions in Supplemental, Intervention Solutions and Professional Services

• Platform + advanced analytics +

continuous delivery = efficacy engine

• Integrate offerings to unlock true value

to customers designed to improve student outcomes

• Increase revenue through cross selling

and upselling go-to-market initiatives

• Standardize IT infrastructure,

streamline back office and standardize product catalog to eliminate unnecessary variation

• Move to Lean Agile Continuous

Delivery model for Software development

• Improve processes and technology to

elevate customer experience

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Transforming from Publisher to Learning Company

Submitted: English on April 6, 2018 • Spanish on May 18, 2018

HMH Differentiators

Financial Overview

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Business Line Billings Growth Framework

Core Solutions Annual growth in line with market Long-term average growth in low single digits Extensions Low-to-mid single digits Trade Low single digits Core Solutions 42% Extensions 45% Trade Publishing 13%

Billings Mix in 2017

Long-Term Billings1 Growth Framework

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2017 Cost Structure

Our Adjusted Fixed Cost Structure Benefited From Restructuring Actions Taken in 2017- Targeting $70-80m in Run-Rate Cost Savings

47%

2017 Adjusted Fixed Costs Percent of Billings1

38%

2017 Adjusted Variable Costs Percent of Billings1

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Variability in Content Spend Driven by Major Adoptions

Program Development commences up to two years before major adoptions

Higher spend associated with:

• Multiple major adoptions in upcoming

two years

• Reading and Math programs

In 2017 the calendar includes adoptions in:

• California Social Studies (2018)
• Florida Science (2018)
• Texas Reading (2019)
• Florida Math (2019)
• California Science (2019)

Note: Amounts are as reported and do not include content spend of the Ed Tech business prior to the May 29, 2015 acquisition.

$127 $116 $104 $124 $139 2013 2014 2015 2016 2017 ($ in Millions)

CA Math FL Math, Reading TX Math, Science CA Reading

First Year

• f Adoption

TX Social Studies

Math Math & Reading Math & Science & Social Studies Social Studies Reading Reading Social Studies Social Studies Science & Social Studies ELA Science

CA Social Studies FL Science

Math

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PP&E Capital Investment Supports Operating Model Transformation

Note: Amounts are as reported and do not include PP&E spend of the Ed Tech business prior to the May 29, 2015 acquisition.

$60 $67 $83 $106 $58 2013 2014 2015 2016 2017 ($ in Millions) PLATFORM

• Ongoing Ed feature enhancements
• Maintenance of legacy platforms

until sunset IT SYSTEMS

• New ERP implementation (planning)
• System updates (ongoing)
• Ongoing maintenance

FACILITIES

• 4 office moves in 2016 (non recurring)
• Modest ongoing maintenance

Major Components

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Looking Ahead

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$11B

Total U.S. K–12 Market Instructional Materials

6 Contributing Members Includes:

• Basal Curriculum
• Program-Based Services
• Educational Assessment
• Coursework

Disciplines Include:

• Math
• Reading/Language Arts
• Science
• Social Studies
• World Languages
• Vocational
• Music
• Advanced Placement

Total AAP Market

• Only includes opportunities

where HMH has products (e.g., excludes Vocational, Music, and Advanced Placement)

HMH’s Addressable AAP Market

Outside U.S. K–12 Market

• International
• Trade

HMH Revenue

Outside AAP but within U.S. K–12 Market

• Practice-Based Services
• Clinical Assessment
• Extensions not included in AAP Market

Understanding HMH Share of U.S. K-12 Market

19 HMH Share of Addressable AAP Market

HMH’s AAP Addressable Market

Projected Market Drivers

Adoption States

• 2018 : FL – Science (K–12)

CA – Social Studies (K-8)

• 2019 : TX – English Language Arts (K-8)

FL – Math (K-12) CA – Science (K-8) and Social Studies (K-8) (year 2)

• 2020 : TX – English Language Arts (6-12)

FL – English Language Arts (K-12) CA – Science (K-8) (year 2)

Open Territory

• State education expenditure growth
• Common Core program replacement approaching

2013 2014 2015 2016 2017 2018P 2019P 2020P

Open Territory Adoption

($ in Billions)

44% 48% 42% 39% 38% HMH Share ($29m) $308m $162m ($86m) ($62m) Free Cash Flow3

~$3.1

TROUGH-TO-TROUGH PEAK-TO-PEAK 20

How We Will Grow Free Cash Flow

• Increase market share in Core Solutions
• Launch of next generation Reading & Math in 2019
• Progress on integrated solutions
• Grow our Extensions businesses
• Invest for future growth (organically, partnerships and acquisition)
• Manage fixed costs to offset inflationary items
• Process and systems re-engineering

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Questions?

Appendix

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2018 Billings2 Calculation/ 2017 Billings2 & Net Sales Reclassification1

• category. Further, certain other products and/or certain other products have been recast between the Core Solutions and Extension categories to better align with the manner that the businesses are now viewed and managed. Lastly, an elimination

entry impacting each of our Education and Trade segments in the fourth quarter of 2017 has been recast to attribute certain revenue to the Education segment originally reported in the Trade segment to better align such sales to the segment selling to the end customer. The Company’s first quarter 2018 quarterly report on Form 10-Q dated May 3, 2018 is the first to reflect the above changes on a comparative basis.

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($ in Millions) 2017 Reclassified 2018 Q1 Q2 Q3 Q4 Total Q1 Q2 Core Solutions Net Sales $65 $176 $277 76 595 $61 $152 Change in Deferred Revenue (19) 9 22 (21) (10) (25) 13 Billings $46 $185 $299 $55 $585 $36 $165 Extensions Net Sales $120 174 $204 134 632 $122 $187 Change in Deferred Revenue (18) (7) 31 (10) (5) (14) 1 Billings $102 $168 $234 $124 $628 $108 $188 Total Education $148 $353 $533 $179 $1,213 $145 $353 Trade Net Sales $37 $42 $51 50 181 $37 $36 Change in Deferred Revenue

• (1)
• (1)
• Billings

$36 $42 $50 $50 $180 $37 $36 Consolidated Net Sales $222 $393 $532 $261 $1,408 $220 $376 Change in Deferred Revenue (38) 2 52 (31) (15) (38) 14 Total HMH $184 $395 $584 $229 $1,392 $182 $389

Note: Details may not sum to total due to rounding.

2013 2014 2015 2016 2017 Cash Flows from operating activities Net cash provided by operating activities $157 $491 $348 $144 $135 Cash Flows from investing activities Additions to pre-publication costs (127) (116) (104) (124) (139) Additions to property, plant, and equipment (60) (67) (83) (106) (58) Free Cash Flow $(29) $308 $162 $(86) $(62) ($ in Millions)

Reconciliation of Free Cash Flow

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$ in Millions Full Year

2016 2017 Cost of sales per Form 10-K $ 802 $ 790 Selling and administrative per Form 10-K 700 655 1,502 1,445 Less: Depreciation - cost of sales (41) (38) Depreciation - selling and administrative (39) (37) Publishing rights amortization - cost of sales (61) (46) Pre-publication amortization - cost of sales (130) (126) Stock-compensation - selling and administrative (11) (11) Restructuring/Integration (14) Legal settlement (10) 4 Fees, expenses for debt/acquisition matters (1) (1) $ 1,194 $ 1,189 % of Billings1 % of Billings1 Fixed expenses $ 673 48% $ 657 47% Variable expenses 521 37% 532 38% $ 1,194 $ 1,189 Net sales $ 1,373 $ 1,408 Change in deferred revenue 38 (15) Billings1 $ 1,410 $ 1,392

Non-GAAP Reconciliation – Adjusted Fixed and Adjusted Variable Costs

Forward-Looking Non-GAAP Reconciliation – Adjusted Fixed and Variable Costs and Free Cash Flow

Management has presented certain forward-looking statements about the Company’s expected future performance on a non-GAAP basis, including adjusted fixed and variable costs and free cash flow. Management is unable to present a quantitative reconciliation of these forward-looking non-GAAP financial measures to their most directly comparable forward-looking GAAP financial measures of cost of sales and selling and administrative expense and net cash provided by operating activities because management cannot reliably predict all of the necessary components of such GAAP measures on a forward-looking basis. The adjusted fixed and variable costs are derived by excluding and/or including certain items required to be included in/excluded from the most directly comparable GAAP financial measures of cost of sales and selling and administrative expense. The determination of the items excluded from/included in adjusted fixed and variable costs is a matter

• f management judgment and depends upon, among other things, the nature of the underlying items recognized in a given period. Management excludes/includes the following

items from adjusted fixed and variable costs and such items may also be excluded/included in future periods and could be significant in amount.

• Interest expense, interest income, tax benefit/expense, depreciation and amortization expense
• Non-cash charges related to stock compensation, asset impairments and unrealized gains and losses for derivative instruments
• Fees, expenses or charges related to the acquisition of other businesses, including purchase accounting adjustments, integration costs and transaction costs
• Fees, expenses or charges related to securities offerings and debt refinancings
• Charges associated with restructuring and cost saving initiatives, including severance, separation and facility closure costs
• Certain legal settlements or awards
• Non-routine charges or gains

Our inability to present a quantitative reconciliation of adjusted fixed and variable costs to cost of sales and selling and administrative expense on a forward-looking basis also prevents us from being able to present a quantitative reconciliation of free cash flow to net cash provided by operating activities on a forward-looking basis.

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