Investor Presentation April 20, 2015 Forward Looking Statements In addition to historical information, this presentation may contain “forward-looking statements.” The words “forecast,” “estimate,” “project,” “intend,” “expect,” “should,” “believe” and similar expressions are intended to identify forward-looking statements. These forward-looking statements involve known and unknown risks, uncertainties, assumptions and other factors that may cause our actual results, performance or achievements to be materially different from any future results, performance or achievements expressed or implied by such forward-looking statements. We refer you to our “Risk Factors” disclosure filed on Form 10-K filed with the Securities and Exchange Commission on March16, 2015 for an extended discussion of the risks confronting our business. The forward-looking statements in this presentation should be considered in the context of these risk factors. The Company makes no commitment to revise or update any forward-looking statements in order to reflect events or circumstances after the date any such statements is made, except as otherwise required by the U.S. federal securities laws or the NZSX Listing Rules. 2 Today’s Presenters Brian Stafford Greg Petersen CEO Executive Vice Chairman 3 Diligent at a Glance 3,000+ Clients & 92,700+ Users ~$89M Revenue Run-Rate(1) Clients in 50 Countries, Product in 5 Languages SaaS Provider of Secure Growing list of Customer Service Awards Communication and Collaboration Tools for Board Members and Best-in-Class Customer Retention Company Executives Preparing to Launch Company’s Second Major Product (1) Based on Q4 2014 Revenue of $22.2 million. 4 Company History 92,700 Users 72,600 Users 2010 Launched iPad App 2007 IPO on NZX 2006 2001 Started Development of Diligent Boardbooks 2007 2012 Opened Australia Office 8,200 Users 4,000 Users 2001 27,500 Users 2008 2007 Opened UK Office 2009 2010 2014 Launched Microsoft Surface Application 5 2011 2012 2014 Launched Product in New Languages 2014 Opened R&D Center in Charlotte 2013 2014 2015 Anticipated Launch of Diligent Teams Product Overview The World’s Most Widely Used Board Communication & Collaboration Tool Seamlessly facilitates confidential document sharing & review Fast, intuitive, feature-rich user experience World-class security and hosting infrastructure Accessible from a variety of devices from any location, at anytime, online or offline Award-winning 24/7 customer support 6 Investment Highlights       Clear Leader in Large Market with Greenfield Opportunities Remaining Scale Creates Network Referral and Investment Capacity Advantages Highly Loyal Blue-Chip Customer Base Demand For New Product in Growing, Global Market Multiple Growth Vectors With New and Existing Customers & Markets Strong Financial Profile Characterized By 28% YOY Growth and 30% Adj. EBITDA Margins in 2014 7 Clear Leader in Large Market with Greenfield Opportunities Remaining  85% of sales to new clients are greenfield  119,000 potential clients worldwide, indicating $3.57B in opportunity 24,000 119,000 EMEA(4) APAC(5) Total Market 54,000 5,000 Publicly-Traded U.S. Companies: Paper / Other: ~50 – 65% 30,000 6,000 Competitor Customers: ~17% – 32% Diligent Customers: 18% 5,000 Publicly-Traded U.S. Co.’s(1) Other U.S. Institutions(2) Rest of Americas(3) Number of Potential Clients 5,000 30,000 6,000 54,000 24,000 119,000 Potential Rev. $150M $900M $180M $1,620M $720M $3,570M (1) (2) (3) (4) (5) US Publicly-traded companies – no revenue minimum Includes all U.S. private entities over $100mm in revenue, higher education and state organizations. Includes public and private entities with revenue over $100mm in Canada, Mexico and Brazil. Includes public and private entities with revenue over $100mm in UK, South Africa, Germany, Switzerland, France, Spain, Italy, Belgium, Netherlands, Luxembourg, Norway, Sweden, Finland, Denmark. Includes public and private entities with revenue over $100mm in Australia New Zealand, Singapore, Japan, Taiwan, Hong Kong, India and Malaysia. 8 Scale Creates Network Referral and Investment Capacity Advantages  Diligent users are likely to serve on multiple boards, creating a multiplier effect for referral sales  Extremely satisfied customers make it easier to close on referral sales  Diligent has the capacity to invest more in customer support & product development than smaller players Estimated Number of Users (Thousands) 93 40 Boardvantage 40 Nasdaq OMX Directors Desk 15 15 15 BoardPad Computershare BoardWorks Thomson Reuters Accelus BoardLink Source: Publicly available information and company estimates. 9 Highly Loyal Blue-Chip Customer Base Representative Customers  33% of Fortune 500  18% of U.S. Public Companies  38% of FTSE 100  95%+ retention rates  Driving expansion into broader collaboration space 10 Demand For New Product in Growing Market Market Opportunity Outside Boards of Directors  Existing Boardbooks clients have already begun to find new use cases for the product ($ Billions)  New Diligent Teams offering designed for a broad set of use cases  ~$18 – $25B market opportunity in next five years(1) $18.1 $19.6 $21.1 2014 2015 2016 Source: IDC. $22.8 $24.6 2017 2018 Bank Loan File Review Job Candidate Resume Review Doctor / Patient Reviews Executive Team Planning Parole Board Asset Management Sales (1) Reflects content management, collaboration, and project and portfolio management 11 Growth Opportunities Expand Footprint Globally & Within Key Industries  Identified 5 key industries that represent a $50M+ opportunity to win new clients and achieve greater penetration in the U.S. market  Investments made in European and Latin American sales forces  Investments underway in the Asia Pacific region outside of Australia / New Zealand Upsell within Existing Client Base  Initial sale generally for specific Board and Director use Cohort Analysis of Contract Value: New EMEA Clients Signed in 1Q12  Following on from initial contract, satisfied clients upgrade their use to include further Boards, Committees and additional use cases outside of the boardroom  Specific case study showing the increase in contract value over time for a group of clients that initially signed in EMEA in Q1 2012 £25,025 £33,883 £17,790 Initial Contract Value Q1 2012 December 2012 December 2013 December 2014 Reflects average contractual revenue obligation across cohort of 28 clients. Note: During the period shown, two clients from the cohort were lost – one as a result of M&A and the other due to a regulatory requirement. Expand Product Portfolio  Clients have asked for more – thousands of users utilize Boardbooks outside the boardroom  Diligent Teams will offer additional tools for collaboration in a growing, global market  Small, strategic acquisitions intended to provide growth opportunities and improved product portfolio 12 £30,903 Financial Highlights 13 Financial Highlights Proven Revenue Growth  Continued revenue growth driven by new customer acquisition and upsell activity $83.1 $64.8  Highly profitable operations from core products enable funding of growth initiatives – Expanded sales efforts – New product development $39.1 $15.6 2011 2013 2014 Adjusted EBITDA Margin Users / Client 26.8 2012 28.8 29.6 34.6% 30.7 26.7% 29.6% (0.0%) 2011 2012 2013 2014 2011 14 2012 2013 2014 Benchmarking Supports Growth Initiatives Best-in-Class Gross Margin Room to Grow through Investment R&D % of Revenue 79% 78% 76% 70% 68% 66% 30% 63% 11% Diligent Box Salesforce Xero Netsuite Workday Diligent Veeva 15% 13% 33% 37% 18% Veeva Salesforce Netsuite Box Xero Workday Efficient Return on Sales & Marketing Spend Versus Comparable SaaS Vendors Revenue Payback (years) Gross Profit Payback (years) 0.7 0.9 Diligent 1.4 1.0 Xero 4.6 4.0 1.1 1.4 Veeva 1.9 1.3 Netsuite 2.7 1.8 Workday 2.9 2.5 Box Source: Most recent public quarterly SEC filings for U.S. reporting companies; Xero based on most recent interim report (revenue payback provided in interim reports adjusted by gross margin for Gross Profit Payback). 15 Salesforce Q1 and Fiscal Year 2015 Outlook Guidance Provided on March 1, 2015 2015 Investment Initiatives ($ Millions) Revenue FY 2014 Q1 2015 FY 2015  Increase salespeople from 23 to 33 globally $83.1 $22.5 – $22.7 $97 – $99  Marketing investment to support sales initiatives YoY Increase 28% 18% – 19% 17% – 19%  Increase R&D headcount from 92 to 118 globally Adj. EBITDA Margin 30% NP 24% – 26% 16 Financial Highlights     Strong Revenue Growth Best-in-Class Gross Margin Significant Growth Potential with Increased R&D and S&M Investment Return on Investment Realized Much Faster than Comparable SaaS Vendors 17 Questions? 18 19 Appendix 20 Non-GAAP Financial Measures This investor presentation presents Adjusted EBITDA, which is provided to investors to supplement the results of operations reported in accordance with accounting principles generally accepted in the United States of America (“GAAP”). We define this term as follows: • Adjusted EBITDA: operating income before depreciation and amortization expense, stock based compensation expense, costs associated with the investigation and restatement of our historical financial statements, and non-recurring costs related to the CEO’s performance cash awards and restatement bonuses. This supplemental measure of the Company’s performance is not required by, or presented in accordance with GAAP. The Company’s management uses non-GAAP financial measures internally in analyzing its financial results and believes they are useful to investors, as a supplement to the corresponding GAAP measures, in evaluating the Company’s ongoing operational performance and trends and in comparing its financial measures with other companies in the same industry, many of which present similar non-GAAP financial measures to help investors understand the operational performance of their businesses. However, it is important to note that the particular items the Company excludes from, or includes in, its non-GAAP financial measures may differ from the items excluded from, or included in, similar non-GAAP financial measures used by other companies in the same industry. Non-GAAP financial measures should not be considered in isolation from, or a substitute for, financial information prepared in accordance with GAAP. For a quantitative reconciliation of Adjusted EBITDA to the most directly comparable GAAP financial performance measure see Appendix 1: Reconciliation of EBITDA to Adjusted EBITDA. 21 Appendix 1: Reconciliation of EBITDA to Adjusted EBITDA ($ Millions) Q4 2014 Operating Income Q4 2013 FY 2011 FY 2012 FY 2013 FY 2014 $3,356 $1,028 ($1,489) $7,616 $10,331 $15,124 831 515 579 1,187 1,645 2,784 $4,187 $1,543 ($910) $8,803 $11,976 $17,908 Investigations & Restatement 0 2,289 0 263 5,571 916 CEO Performance Cash Awards & Restatement Bonuses 0 1,253 0 0 2,227 2,756 1,265 1,356 908 1,384 2,581 3,033 Adjusted EBITDA $5,452 $6,441 ($2) $10,450 $22,405 $24,613 Adjusted EBITDA Margin 24.6% 35.4% NM 26.7% 34.6% 29.6% Depreciation & Amortization EBITDA Stock Based Compensation 22