Litera on r/legaltech

Hi! Thanks for these notes. If you are open to it would love for you to spend 30 mins our product team sharing some of these insights directly. You’ve highlighted some decent annoyances and I wonder if we can nip them quickly. On your point for pricing for small firms. We have 15000 customers and nearly 60% are small/medium sized firms of corporates. I often find that price isn’t the issue but rather the exposure to the technology. Basic compare as a tool is \~$50/month/user for a small firm.

To add from my product team: If saving a track changes output from Litera Compare the name of the track changes author is determined by the options set in the comparison styles. This can be changed in the Edit Styles dialog:

https://preview.redd.it/gdv4pvggm15g1.png?width=1413&format=png&auto=webp&s=b3790bedc2eccf965a9cc9029e2687b9f84c00b0

I am really curious on this output. Would you mind spending a few minutes with our product team on this? This rarely comes up as an issue and I wonder if it is a setting issue or something else.

From product :) - This is likely referring to our 'floating panels' feature. Changing this option from the File - Settings menu will help provide a more normal window experience:

https://preview.redd.it/1oyhqbqom15g1.png?width=960&format=png&auto=webp&s=5e102672eb72adee5b0cb6c9f9b28cc0467b9006

Ive probably walked away from over 25 deals. A handful mid cycle and maybe 1 or 2 near the end. Ultimately what made me walk away is defensible nature of the tech, customer usage, or how hard it would be to build natively in our environment. Right now, looking at GenAI "first" companies requires significant diligence on security, difficulty to duplicate and uniqueness.

Happy to talk through this for you and your firm. I hear this a lot but can tell you internally we do not have a mandate to increase price for the sake of increasing price. While we do work through pressures of inflation/CPI, our price increases outside of that are tied to adding more skus, seats, or usage. If you have experienced something different, please DM me and I am happy to run this down!

Great question! When we look at the pricing of our products we look at the tools that lawyers/law firms acquire, the value the products generate and how often they are used. Across the board, on a per user/per month basis our products tend to be in the middle or actually on the low end. For example, if a firm with 500 lawyers bought everything possible from Litera, that price per lawyer per month would be significantly less than what some new entrants are charging for one or two products.

Our approach to Lito is definitely unique in market. We released Lito a few weeks ago and offered to our customers that have drafting or Kira the product at no cost. Lito shipped with 20 skills today and 400 in backlog. I fundamentally believe that the value GenAI brings today is not $300/user/month but a fraction of that. Lito is a direct reflection of that belief. Over time, there will be some skills that come to market with a cost associated and some at no cost. That variability is based on value, effort and outcome. We are also seeing customers leaning in and developing bespoke skills on Lito. The exciting thing about Lito is that it leveraged 30 years of rules based engines and makes them super powerful.

To double click on this. With Litera One and drafting moving to the cloud, I have assured the market that we will continue to support/innovate our desktop apps. However, as noted below we will push customers to the latest versions of those desktop apps. As much as we want to believe everything can be in the cloud, I do know that associates want the comfort of knowing they can compare a document without internet. This wont be forever. At some point, Microsoft will fully shut off VSTO com add-ins.

True, we are private equity owned but this business does not run on any timeframe. As you may know, I was the CEO from 2016-2022 and then returned last year. During my first term, we consolidated many legacy tools that had existed for 10-15 years. During this time the tools accumulated significant technical debt as firms would ask for one-off customization/configurations for their unique environments. One of the pro’s of being a desktop application is that you can do so much with it in your environment, but it makes it really difficult for the software company to manage. When I came back last year, I found hundreds of versions of all of our desktop apps deployed throughout the ecosystem. Quality and consistency was lacking. As of the end of Q1 2025, we launched our go forward web applications built on modern infrastructure and to date we have had 8,500+ customers migrate to this ecosystem. That is roughly 50% of our customer base. Our goal is to get the entire 15,000 customer base onto our go forward cloud desktop solutions, provide a modern singular desktop application for the near term, and manage one code base with configurations v. customizations. The customers that have taken the new applications are finding the tools to be faster, more consistent and of higher quality. These new versions in the cloud also have significant investments and features leveraging GenAI. Litera is 100% built to last the next few decades and getting our customers on to the latest versions of our software is key to that success.

1) As in house counsel, I would ask questions around deployment methodology, global support, security and integration point of view. All technology, today more then ever, needs to integrate with each other. The key to successful use cases with GenAI is the ability for core data to be accessible and movable between workflows. Also, security is more important today then ever before. With the spike in start-ups in the legal industry it is a clear opportunity for bad actors to test and look for holes. Finally, being able to support you where and when you work is key.

2) I practiced law for a few years in Chicago for a firm focused on the natural food and drug industry. My work varied from Trademark searches and filings, to regulatory submissions, and business/trademark/copyright litigation. As a first year I was humbled by spending time bate stamping documents, reviewing labels, reading search results and almost never speaking to a client directly. As I moved on started my own practice, I saw the value and insight gained when working with clients directly. From there, I spent 4 years in Legal IT Consulting. Providing tier 1 Help Desk, Managed Services and Engineering support to 1000+ law firms. I learned the struggles that lawyers face everyday with technology, the issues and concerns if IT admins and ultimately what the partnership needed for outcomes. All of these experiences, plus having friends that still practice at the highest level influence our products. I truly believe that the Attorney/Client relationship is critical and vital and technology should not get in the way of it but rather support and promote it.

I think there are truly 5-7 global legal tech companies. In my mind we all play nice in the sandbox and leverage each others know how to improve the outcomes of our end users. For what Litera brings to bear in the market, selfishly as the CEO I believe we do what we do the best. The comprehensive nature of our offering, ability to be parsed out based on customers need, and now delivering innovation with GenAI we are uniquely positioned to leverage 30 years of rule based engines for long term generation of value for end users and their clients.

Great question and thanks for highlighting the improvements. We have spent the year focused on quality and responsiveness and listening. Let's make sure we understand your challenges and address them as quickly as we can.

With that said, it is true that we find restrictions in testing as customers have configured Foundation unique to their culture. Our Dev/QA teams are interested in learning what those configurations are and pre-testing them for you ahead of time. More to come here, but please do reach out if you are interested in working on helping us pre-test. We can also, test a build in your staging environment in a supervised session.

1. Open the Edit Styles dialog.
2. Select New and create a name for your new style set.
3. Check the "Show moves in n words or more option" (we recommend setting n to 5).
4. Select OK to save the style set and use this for future comparisons.

https://preview.redd.it/sxhdx4nyo15g1.png?width=1363&format=png&auto=webp&s=1860e3937983504bfed564527384537a53d7be70

Ah! great question and this is available!! With our newest Compare experience available in Litera One for Web, users can run up to 20 comparisons (40 documents) at once and receive all 20 redlines in one shot.

As someone who recently bought both of these services I am hopeful that the actual product become commoditized. The reason for this is so that more of the spend can go to the attorney for actual thoughtful conversations, planning and execution. The actual documentation at this point is not hard but the planning and conversation is more important. Those are services we all will pay for.

This is a real interest of mine. For now, we are finding great partners to work with on integrations with Foundation. Unicourt and Courtroom Insights are just of the companies that integrated their data into Foundation for our mutual customers. More to come in this space as we continue to look for areas to bring real time date and insights into the work that is happening today.

Tough question :) FWIW have very little regrets of companies we didn't buy or lost to TR. The market and technology has moved so quickly the past 24 months that it is now more important to leverage internal DNA for building new v. always buying the next new opportunity.

I think we are early days on this. We do have a case matter management tool but that is focused more on the business of the case v. the actual court proceedings. I know there are a few companies focused on this specific interaction of court deadlines/requirements and team coordination and it is an area that I am watching.

Hi- Thanks for letting me know and not at all what I would expect from my team. If you want to email me directly, I'll have someone reach out immediately. Would love to see if we have improved the experience of PDFdocs to earn your partnership back.

I am huge Chicago sports fan and self proclaimed sneaker head! Went to my first cubs game as 4 month old, got to see all 6 Bulls Championship runs, see the Cubs win the World Series, throw out a first pitch and take my 2 girls to a game. And sneakers are my vice. Oh and all round foods: bagels, pizza and baos :)

This question has come up alot on how we will support version upgrades in Litera One. Similar to other SaaS products we will push updates as they happen, however we do understand that firms could use a bit of time in "staging". We are thinking through what this means. Our business is now built to release versions quickly and more often so balancing the need to get quality updates out and innovation with some firms need to test is a balance we are finding.

I think the 3 items you have noted are clear lanes to be driving the business in. The other is to be very clear quickly what your ideal customer profile is and being true to that. I believe Y-Combinator just came out and stated that want to invest in businesses that can get to 12M in 12 Months. The ball keeps moving down the field to measure success. Especially in this age of VC investing and outcome expectations.

Sounds like you have some great experiences and DNA. Finding the right company is like finding the right product market fit. Often times this can take a few turns to find a spot that works. I would not get frustrated as the market has gotten tight but companies are always looking for smart, growth minded talent.

This is an unfair question :) I will say this. The market would be surprised by some of the darling tech over the years and currently in market. When we actually get under the hood of a business before or after acquisition there are always cobwebs. If we move forward with the business, we now own the cobwebs and making sure they are removed. This often comes across that Litera has broken the business after acquisition when in fact we are strengthening for the scale and long term innovation opportunity. But in the short term, it can come across as disruptive.

There is great upside for firms under 10 people. Our job with technology is to work with each other. In this market you are probably using Clio or other PMS's of similar stature. We can do more to deliver our technology alongside which will help with deployment, training and usability. We are also considering a different model down market for some of our legacy enterprise products that could provide meaningful ROI for this segment. I just had a conversation with leadership today about a deliberate focus on this segment. If you are open to it, would love a short conversation to brainstorm a bit.

You raise a great consideration for me. We've always supported legal aid clinics but I think we can look to expand that view. Will take this away and find a way to offer programming to this segment. I think A2J is an area that can have a material impact with the tools that exist today.