Legal Tech Veteran Derek Miller, Former inData CEO Who Oversaw Trial Director, Joins Lit Software to Help Drive Enterprise Growth of Its Litigation Suite

Derek Miller, a veteran legal technology executive who, as president and CEO of inData Corporation, oversaw Trial Director, one of the most widely used trial-presentation software products ever, has joined Lit Software, the developer of a suite of litigation apps for iPad and Mac, as a strategic advisor and director of enterprise, where he will help drive the company’s continued expansion, particularly into larger firms, corporations and insurance companies.

For nearly 30 years, from 1989 to 2017, Miller was with inData Corporation, most of those years as its president and CEO. He oversaw the company’s transition from a services company, converting deposition transcripts to electronic text, into a leading provider of case management and evidence presentation software. During his tenure, the company launched two market-leading products, Trial Director, which came to be used by at least 90% of the Am Law 200, and TimeCoder Pro, for creating searchable, synchronized transcripts and videos.

When e-discovery company Ipro acquired inData in 2017, Miller moved there, taking on the role of vice president of product solutions until he left the company in 2021.

Since leaving Ipro, Miller has been an advisor to businesses on sales and marketing strategies, product development and product roadmap management. He is also a trial consultant on presentation strategies and technology solutions, a role in which he has consulted on a number of high-profile cases, including to the Los Angeles District Attorney’s Office in its prosecution of Robert Durst.

Lit Software, founded in 2010 by Ian O’Flaherty and Tara Cheever, is the company that developed TrialPad, trial presentation software that was the first legal-specific app developed for the iPad. It went on develop TranscriptPad, for reviewing transcripts; DocReviewPad, for reviewing documents; and ExhibitsPad, for organizing trial exhibits. Its Lit Suite bundles three of those apps — TrialPad, TranscriptPad and DocReviewPad — in a single subscription.

Enterprise Expansion

In an interview Friday with Miller and O’Flaherty, Miller said he is joining Lit Software in a dual role. For one, he will be a strategic advisor, using his experience and contacts in the industry to help move the company farther along in its growth. Second, he will be director of enterprise, leading enterprise-level sales to law firms, corporations, insurance companies, and other organizations that prefer to buy the apps through enterprise licenses instead of through Apple’s App Store.

With a long history in litigation software, Miller joined inData six months after its founding as a vice president, and became president and CEO in 1995. A year after he became president, the company released Trial Director, which eventually came to be used by at least 90% of the Am Law 200 — probably closer to 100%, Miller said.

O’Flaherty, describing Miller as “the grandaddy of trial presentation,” said he will fill an important role in helping Lit Software expand within the enterprise market.

With its products offered as iPad apps, they were initially used primarily by lawyers in smaller firms and for smaller cases. But over the years, the company increasingly saw interest from enterprise customers at large law firms, insurance companies, government agencies, and the likes, all of which wanted a way to license multiple copies of the individual apps or of the Lit Suite.

When the company began to offer enterprise licenses, that market began to grow quickly, O’Flaherty said, and he realized that “we needed someone of Derek’s caliber to be in here to help manage these large enterprise clients.”

At the same time, the company is preparing a notable product enhancement and a new product roll-out. It is beginning to incorporate artificial intelligence into its TranscriptPad app, which will allow lawyers to synchronize video depositions with the deposition transcript directly on an iPad or Mac.

Also, the company is beta testing and preparing to release a new product, TimeLinePad, for creating litigation timelines.

With all that going on, O’Flaherty said, “we needed someone of Derek’s experience and knowledge and caliber to help us drive the company forward. … Derek’s had the experience of having been there and done that.”

Future Plans

Since leaving Ipro in 2021, Miller has continued providing trial consulting services, but he has also advised startup businesses on preparing for new investments or acquisitions. Given that, I asked whether part of his reason for joining Lit Software was to help prepare it for a potential investment or acquisition.

Other than a small initial seed investment when it started, the company has been bootstrapped and has never taken a major outside investment.

Miller said there are no immediate plans to seek an investment or acquisition.

“I think there are certain things we can do to set Lit Software up to succeed, so that if that is the choice they make at some point going forward, they will be able to do that,” Miller said. “The nice thing about it is its not a requirement, it’s an option.”

O’Flaherty said the company has been successful virtually from the start, launching TrialPad, its first iPad app, just 10 months after the iPad first came to market in 2010.

Now, with Miller joining the company, he said is looking forward to the company’s next stage of success.

“With Derek coming on board, we not only get a seasoned industry leader, but also an exceptional visionary who’s recognized the immense value that we bring to the table,” O’Flaherty said. “His decision to join us is a testament to the trust and confidence placed in our capabilities and our software solutions.”