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Matthew Small is general counsel of Blackboard, a D.C.-based education software company that provides electronic education software and other services to schools and businesses in the United States and abroad. Tell me a little bit about Blackboard. What does the company do? Blackboard is an enterprise education software company founded with a vision of transforming the Internet into a powerful environment for teaching and learning. Blackboard has played a huge rule in improving the educational experience by bringing schools online. When you and I went to school, we would go to class, get the reading assignment, textbooks, and so on. Today, students have online reading assignments, and calendars online; they can take tests and quizzes online; they can chat with other students. That has just become a part of university life. Blackboard provides the software the university uses to go online. How did Blackboard get started? The company was founded in 1997. At the time, the Internet was becoming hugely popular, and people were using it for things like e-mail, and companies were scrambling to sell things online. Our founders, Matthew Pittinsky and Michael Chasen, saw the Internet as a powerful medium for education and realized that universities were going to need software to power that tool. Blackboard created a software application that was easy to use and very scalable. Any teacher could upload documents, and create tests and quizzes. Right now, the software is used at more than 2,000 institutions. We’ve also evolved, and now serve the U.S. K-12 and international post-secondary markets. The demand is huge, and I think the country is going to get to a point where parents will take it for granted that they can see their kids’ records and grades online. Blackboard produces what it calls “suites”: the Blackboard Academic Suite and the Blackboard Commerce Suite. The Academic Suite is used by institutions to manage their entire academic system: courses online, teachers’ content, and also an online community. Teachers can create a class, or they can manage all of their educational content. Students can go online to sign up for a college organization, buy tickets to a game, or enroll for a class. There is now one place online where students can go for everything they used to be able to get only in a traditional brick and mortar institution. The Commerce Suite deals with student cards. In the past, students had an ID card. They may have also had separate cards for the cafeteria, the copy machine, and the student union, and then keys to get into doors. Now all of that is in one card. Blackboard provides hardware that’s installed at the universities. We put “access readers” at doors, in cafeteria vending machines, copy machines, laundry machines. Students can also put money on cards and use them off-campus. What can you tell us about your job as general counsel? As general counsel, I’m the chief compliance officer for the company and have the chief legal responsibility for all regulatory work, all corporate legal transactions, and contracts. Because Blackboard has an annual subscription model, we have thousands of clients all on annually renewable licenses. So our contracts involve both signing up new clients each year and renewing prior clients. In our contracts group, we have six nonlawyers. I would put them head-to-head with any licensing attorney. They negotiate our form agreements day in and day out, and have learned just about every compromise and “work around” possible. They have become very familiar with each state’s licensing requirements, so much so that they often help public schools work through their own state procurement procedures. The head of the contracts group reports to me, but generally, the group is autonomous. If a deal is of a certain complexity or has a certain value, however, then they bring it to the legal department. We have a legal staff of three attorneys. Legal also handles the strategic and business deals on the contract side. Beyond software licensing, our legal department handles corporate finance and securities, mergers and acquisitions, labor and employment, intellectual property, real estate, and tax issues. We have varying degrees of expertise in-house, and tend to do a lot of our periodical government reporting and mergers and acquisitions internally. Who is your outside counsel? We mainly use Wilmer Cutler Pickering Hale and Dorr. We went public in June and they did a great job on the IPO. We also use Patton Boggs for labor and employment and Katten Muchin Zavis Rosenman for copyright and trademark issues. What would you say are the biggest challenges of the job? In addition to time management, which is always a challenge, finding the appropriate balance between the amount of work we do in-house and the amount we send outside can be difficult. I am a firm believer that companies are better served when in-house counsel put in the hours and draft things themselves. The work can be reviewed by outside counsel, rather than the other way around. It’s more cost-effective, and doing work this way keeps all the members of the in-house group very sharp. I also think that there are a lot of questions involved, especially in licensing, that an outside attorney can’t answer. I think that a lot of in-house counsel shy away from securities work and don’t do their own securities filings until the company has reached a certain size. We’re fortunate that we’ve been able to hire people with a regulatory background. Where are you located? We are in Washington, D.C., at Dupont Circle. We may be the only public software company in the District. We have a fun, energetic, bright group of people who are highly motivated. We think that people can socialize in a more exciting environment. It’s more expensive to be here, but this investment means we’ve been able to attract the best and the brightest. What’s the most fun part of the job? Being able to negotiate as counsel for the company and as an officer of the company. For instance, when I’m at the negotiating table in an acquisition, it’s very empowering to know Blackboard’s position and to make my own business calls without having to defer to my client. To the extent it’s a negotiable point, I can negotiate. This puts Blackboard at an advantage in deals opposite outside counsel. What’s your background? I was at Testa, Hurwitz & Thibeault in Boston before Blackboard. While I was very fond of the firm and learned so much there, I find being in-house much more enjoyable. The hours are about the same, but it’s more fun. At Testa, I was an associate in the business practice group. I focused on public and private finance and securities, and on mergers and acquisitions. Since Testa is a high-tech law firm, I also did a lot of licensing. It was a breeding ground for in-house counsel! Who do you report to? I report to the CEO, Michael Chasen. Blackboard has about 500 employees: more than 250 in the District, 125 in Phoenix, 50 in regions throughout the United States, and about 40 internationally, including at offices in Amsterdam and Tokyo and a joint venture in Beijing. What do you like to do in your free time? I love to ski. It was easier to do that in Boston. Here, you have to get on a plane. I also love hiking and outdoor sports. What’s the best book you’ve read recently? Moneyball, by Michael Lewis. It’s a fun baseball book and also a business book. It really teaches you to look at the actual statistical benefits of the decisions you make, rather than relying on traditional methods.

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