Legal Law

Women of Legal Tech: Tara Cheever


The Legal Technology Resource Center’s Women of Legal Tech initiative is intended to encourage diversity and celebrate women in legal technology. This initiative launched in 2015 with a list of innovators and leaders in legal technology and with this year’s additions, that list now includes 141 talented and influential women leaders.

Tara Cheever is the Co-Founder and Chief Products Officer at LIT SOFTWARE, LLC. Since 2010, she has assisted in the design, development, and marketing of TrialPad, TranscriptPad, and DocReviewPad, available for iPad and Mac as a part of the LIT SUITE. Through LIT SOFTWARE, Tara pursues her passion for leveling the legal playing field, putting easy-to-use, and powerful tools in the hands of legal professionals of all backgrounds and abilities. 

All three LIT SUITE apps are used extensively by legal professionals ranging from solo practitioners to Am Law 100 firms, by large corporations and insurance carriers, and by prosecutors, defenders, the United States Department of Justice, and other government agencies. The LIT SUITE is also widely taught in law schools across the United States and has been featured by Apple on the App Store.

Please give us three points to summarize you and your work in legal technology.

I co-founded LIT SOFTWARE with Ian O’Flaherty in 2010. I assist in the design and continued development of the LIT SUITE apps – TrialPad, TranscriptPad, DocReviewPad, and ExhibitsPad (plus another one on the way!) to help democratize legal technology and even the litigation playing field. I am constantly on the lookout for high-bar legal tasks (i.e. expensive/frequently outsourced tasks, or tasks that only complicated technology is available for) that LIT SOFTWARE can create approachable and streamlined solutions for.

How did you become involved in legal tech?

I began working in a technology-driven trial presentation and litigation support company owned by LIT SOFTWARE Founder Ian O’Flaherty. There I learned many legal technology solutions, but all of them were both complex and expensive. When the iPad came out we saw it as a way to simplify and lower the cost of trial presentation. We released TrialPad in the end of 2010, and it has helped democratize legal presentations, reducing or eliminating the use of outside consultants and complex technology. We’ve continued developing along the same philosophy, making easy-to-use and inexpensive apps that are just as sophisticated as the staid technology and processes they are designed to supplant.

What projects have you been focused on recently?

I’ve been working on bringing on-device syncing technology to TranscriptPad. Now you can bring a video into TranscriptPad, sync it with the transcript, and edit, play, and export clips based on page line designations. The technology uses Natural Language Processing and employs Machine Learning to create a very accurate sync, and because it is all on-device, it is fully confidential and never needs to be uploaded to a cloud or an outside service. It is available in a free public beta to all our customers now, and we are still iterating to make it the easiest way to edit and play back legal video.

What do you see as the biggest challenge in legal tech today?

I think the biggest hurdle in legal tech has been the same for a while – getting practitioners to adopt the tech. I hope that will change as the technologies offered become less more straightforward and user-friendly.

What legal tech resource helped you the most in your legal tech career?

Legal-focused blogs, podcasts, and speakers. There are so many people with expertise and great information to share.

What do you see as the most important emerging tech, legal or not, right now?

I think everyone would immediately think of generative AI, but I disagree in the short term. Short-term I think it is the collective technology understanding that young lawyers are bringing to the table upon graduation from law school, and the excellent legal-specific technology training many of them are learning in their law program. Most of those new lawyers grew up with technology that some senior partners are still hesitant to use.

What do you see for the future of legal tech?

Pervasiveness. Paper files that have gone the same place quills and scrolls went, and interactive, easy, and approachable solutions for everything.

What advice would you give to other women who want to get involved in legal tech?

Dive in! The water is warm. There is a place for anyone with initiative, imagination, and the will to apply work to both.

Give a shout-out to another woman in legal tech who you admire or have learned something from!

Since I first started attending the ABA TECHSHOW, Adriana Linares has stuck out in my mind as a woman who understands so many aspects of the legal tech world, and who is approachable and knowledgeable.

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