1. Product Development Listening Session Roadmap Highlights and Open Discussion September 14, 2015 George D. Calvert Senior Vice President Product Development

2. Product Development Listening Session Any statements in this presentation about future expectations, plans and prospects for Blackboard Inc. — including statements about Blackboard, the Building Blocks program and any other statements containing the words “believes,” “anticipates,” “plans,” “expects,” “will,” and similar expressions — constitute forward-looking statements within the meaning of The Private Securities Litigation Reform Act of 1995. Actual results may differ materially from those indicated by such forward- looking statements as a result of various important factors, including product development and other factors discussed in our Registration Statement filed on Form S-1 with the SEC. The forward-looking statements included herein represent Blackboard’s views as of September 14, 2015September 14, 2015September 14, 2015. Blackboard anticipates that subsequent events and developments will cause our views to change. Any information herein relating to our product roadmap is intended to outline our general product direction and it should not be relied on when making a purchasing decision. However, while Blackboard may elect to update these forward-looking statements at some point in the future, we specifically disclaim any obligation to do so. These forward-looking statements should not be relied upon as representing Blackboard’s views as of any date subsequent to September 14, 2015September 14, 2015September 14, 2015.

3. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Slide 3 MISSION CRITICAL EXPLORATORYSUPPORTEDSTRATEGICTRANSFORMATIVE PHASE 1 PHASE 2PHASE 3PHASE 4 PHASE 5 The Networked Learning Environment THE NETWORKED LEARNING ENVIRONMENT ADOPTION + GROWTH Evaluations & Outcomes Management Student-Centered Learning Access to High Quality Content Instructor Efficiency Anytime / Anywhere Access

4. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Slide 4 MISSION CRITICAL EXPLORATORYSUPPORTEDSTRATEGICTRANSFORMATIVE PHASE 1 PHASE 2PHASE 3PHASE 4 PHASE 5 The Networked Learning Environment THE NETWORKED LEARNING ENVIRONMENT ADOPTION + GROWTH Evaluations & Outcomes Management Student-Centered Learning Access to High Quality Content Instructor Efficiency Anytime / Anywhere Access

6. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Slide 6 Blackboard Backpack™  Student productivity through take-it-with-you synchronization Course content Announcements Calendar items Tasks  Server to the Windows PC New items added to queue for each user Sysadmins manage load on servers (7.0) —Schedule when synchronization available —Control file size, wait times, etc. —And can disable for all students

7. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Slide 7 Blackboard Backpack™

8. Evaluations and Outcomes Management

9. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Slide 9 Recent News “One of our biggest challenges is a lack of compatible and comprehensive measurements — the kind of information parents have come to expect from K-12 schools.” Margaret Spellings US Secretary of Education First Public Speech, February 2005 “Assuring the quality of higher education in America was once a straightforward, if tedious, proposition … Accrediting commissions, and their member institutions and faculty, shared a rather complacent approach to academic quality, assuming that as long as the proper resources were in place and the people using them were faithful stewards, good learning (or at least acceptable learning) would follow. Those days … are long gone” Jon F. Wergin Principle Investigator, Council of Regional Accrediting Commissions Change Magazine, January 2005

10. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Slide 10 Plan. Collect. Evaluate. Plan. Collect. Evaluate.

11. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Any information herein relating to our product roadmap is intended to outline our general product direction and it should not be relied on when making a purchasing decision. Slide 11 Project Caliper  Plan. At all levels of the institution Structure strategy for the institution Develop intended learning outcomes for each program Establish rubrics for objectives  Collect. Data and results through many instruments Enterprise-wide course surveys and program-level testing Evaluation portfolios and assignment "binders" Connecting with all Academic Suite data  Evaluate. For continuous improvement Compare results with objectives – over time Demographic analysis, trend analysis, etc. Define follow-up action plans Close the feedback loop

12. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Any information herein relating to our product roadmap is intended to outline our general product direction and it should not be relied on when making a purchasing decision. Slide 12 For Example  University Strategic Planning  President’s staff documents strategic plan through 2015 and requests annual accounting from all academic and administrative departments.  Accreditation The College of Engineering aligns the various courses they offer to the ABET-defined learning objectives and collect data that shows how their students' outcomes meet those objectives.  Course Evaluation  Office of Instruction emails reminders to students to complete course evaluations by the end of the week. Student completes the course evaluation from home and provides recommendations for improving lab time. The Office of Instruction reviews this feedback for program improvements.  Reporting  Principal runs a report for her school on 5 th -grade math tests versus state standards for the current year – grouping by race and gender.  Student Outcome Tracking  Instructor aligns key student assignments to program learning objectives with an associated faculty-committee -developed rubric.

13. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Any information herein relating to our product roadmap is intended to outline our general product direction and it should not be relied on when making a purchasing decision. Slide 13 REPORTS STATUS MONITORING PROJECT CONCLUSIONS CUSTOM System Overview INSTITUTION (a hierarchy of Operating Units) ASSESSMENT PROJECT OBJECTIVE 1 OBJECTIVE 2 OBJECTIVE N PLAN COURSE (at Section level) USER COLLECT PORTFOLIOS LEARNING SYSTEM STUDENT INFO SYS EVALUATE CONTENT GRADEBOOK SURVEYS

14. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Any information herein relating to our product roadmap is intended to outline our general product direction and it should not be relied on when making a purchasing decision. Slide 14 Capabilities under Analysis  Assessment Management Project tracking and workspace Institutional objective management 3rd-party standards  Enterprise Test and Survey Program-level testing Enterprise-wide surveys for course evaluation External users (e.g. alumni, employers, etc.)  Student Outcome Planning / Tracking Evaluation portfolios Assignment binders Alignment of learning content and activity

15. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Slide 15 Our Turn to Listen

16. ©2005 Blackboard Inc. All rights reserved. The contents herein are proprietary, confidential and, when forward-looking, covered by the safe-harbor protections in SEC regulations. Slide 16 STEERING COMMITTEE GREATER COMMITMENT Keep the Discussion Going The Blackboard Idea Exchange Focus Groups Strategy and trends Messaging and concepts Frameworks and best practices Establishing and evolving standards Product Surveys New features Enhancements Discussion Boards Regular features Timely subjects Market-specific feedback (e.g. K-12) Scheduled Work Collaboration in analysis and design Preliminary feature reviews Ongoing access to PD project leader for specific timeframe Access to early builds on PD server Beta Production testing of new product releases Structured feedback on product Special access to software engineers Early Availability Evaluate new releases Test servers only MESSAGING LOUNGE PRODUCT TESTING EARLY DEV DIALOG DEVELOPMENT PARTNERING

17. Thank You September 14, 2015 George D. Calvert Senior Vice President Product Development