Source: Legal Evolution PBC

T-shaped professionals building one-to-many legal solutions

If you’re a lawyer, is it worth your time to read a detailed post on the development and deployment of high-quality legal software?

Let’s rephrase the question: Do you want to develop sticky and rewarding client relationships while also developing new—and potentially large—revenue streams that have nothing to do with billing more time?

Value-add software can build a protective moat around your client base.

Circa 2021, these types of commercial opportunities are everywhere. This is because software enables lawyers to be more efficient and productive;  and when it’s designed specifically for the business and legal needs of clients, the clients feel more organized, valued, and in control.  To switch providers is to make their lives more difficult. So they don’t.  If “software is eating the world,” see Marc Andressen, “Why Software is the eating the world,” WSJ, Aug 20, 2011, let our competitors, who are disinterested in software, go first.

But here’s the catch—these lucrative and endurable opportunities are profoundly multidisciplinary, which as regular readers know, is a running theme on Legal Evolution. See, e.g., Post 075 (Jae Um noting that “modern law is a team sport” among lawyers and allied professionals); Post 126 (human capital map of one-to-many legal solutions spans multiple disciplines); Post 174 (high-performing multidisciplinary team in Village MD’s legal department) Post 210 (Jason Barnwell discussing law’s “wicked problem” and how solving it requires “[e]arly career legal professionals [to] acquir[e] skills that complement their substantive legal capabilities”).

We are business-oriented technologists, not lawyers. We became legal technologists only through continuously learning more about the legal field, including the intricacies of product liability and mass tort litigation. This is because the larger objective is outstanding commercial results for Xerdict Group LLC, a wholly owned subsidiary of litigation boutique Tanenbaum Keale LLP, where Ken (a regular LE contributor) works as Chief Operating Officer and Matt, an intern, focuses on testing and quality assurance efforts for a new release of our software.

We are most effective at our jobs when our lawyer stakeholders understand some of the fundamental pillars of our discipline. Obviously, this requires an investment of time. The purpose of this post is to drop the investment cost by offering an accessible primer on one allied discipline–the development and deployment of high-quality legal software.

In this post, we’ll examine several key drivers of quality in legal operations technology, including some tips on how to best develop software, the value of common legal standards, how to best take advantage of legal marketplaces and options for deploying individual legal applications in the cloud.

I. Internal Software Development

“Internal Software Development” refers to software a law firm or corporate legal department chooses to create with their own programming staff.   Sometimes they are referred to as incubators or subsidiaries.  Some examples might include Littler’s Compliance HR entity or Reed Smith’s Gravity Stack.

When law firms choose to go down this path, it’s important to follow “rules of the road” to be sure the tech products are top-notch.  It’s really not all that different from lawyers having work product reviewed by different attorneys to ensure quality.

In this section, Matt (yes, Ken’s able and talented son!) will articulate key steps and the value of creating and automating a formalized and automated test plan; storing program code in a source code repository (much like lawyers store documents in a document management system); and the benefit of documenting the results of software tests, both the successful completed tests and defects which require correction.

Ken recently gave a CLE on technology security suggesting that lawyers will never become CIOs. However, pursuant to recent change in the rule on lawyer competency, see Model 1.1, cmt 8 (lawyers have duty to “keep abreast of changes in the law and its practice, including the benefits and risks associated with relevant technology”), they do need to know “enough to be dangerous” in this field.

One might contend the area of software quality is not dissimilar to that.  Attorneys don’t need to learn how to develop high-quality applications.  But they are well served to have requisite knowledge to be sure they are using solid applications.  Here are some rules of the road which hopefully serve as a useful roadmap for legal professionals considering new technological tools.

A. Formalized, Automated Testing

Most of the law firm partners and corporate legal department leaders we’ve worked with insist on work product review prior to finalization.   That is, naturally, an excellent practice.  Putting another set of eyes on something — especially if said “other set of eyes” has complementary expertise (an IP attorney looking at a technology consulting agreement, for example) — clearly reduces the risk of error and improves the effectiveness of the work product.

Well, software testing is really no different.  Traditionally, in the industry, we ask developers (programmers) to unit test their code, which means to make sure the basics of an individual function work.  Then we ask a formal testing group to write and execute a more formal test plan, which is designed to ensure the entire application is operational.

Again, to repeat what will be a common theme, attorneys don’t need to know how to test. But they certainly should be able to ask the right questions to confirm that sufficient quality assurance efforts have been undertaken for any application or process it is considering for use. You want careful, knowledgeable lawyers reviewing legal work; likewise, you want developers adhering to cost-effective quality controls that avoid failure or error.

Matt’s work at Tanenbaum Keale focuses on improving the testing process for new Xerdict products.

Like many functions, testing is an area where automation is all the rage.  Products offering end-to-end test frameworks, like Cypress or Robot Framework, offer testing groups the ability to automate tests.  Like any function, if one can build some code so that common tasks can be shifted from man to machine, the “Build Once, Execute Endlessly” permits maximum levels of testing at the lowest possible cost.

What is the benefit of testing automation?  One legal example might be an interrogatory for similar matters. During the process, certain questions are presented in a logical order.  But the order will vary based on responses (e.g. if someone indicates they interacted with your client’s product, the questions will go down one path—but, if not, the lawyer will skip a set of questions and move on to other area).

So, what are some common use cases for testing automation for legal technology?  Well, consider a process such as logging into a system.  This should look and perform the same way over time. If one can automate this test, we can ask the computer, not a human to do so.  Another example is automating a test for something users do over and over.  Things like adding the initial complaint PDF file to a case management system or entering a dismissal date come to mind.  Legal professionals do this frequently so automating the testing for this common function saves time and money.

Industry expert John Hall, a senior developer at Corridor, Inc. with over twenty-five years of experience developing web-based applications for the legal vertical, observes that “[i]n addition to the ‘write-once, execute forever’ benefit of automated tests, they also serve as a mechanism for capturing and documenting testing knowledge.” In turn, that data speeds up the overall process of knowledge transfer and continuous improvement.

While many tests can be improved with automation, certain tests can require more hands-on type of testing. Custom testing is not always something that can be tested by automation.  Indeed, writing an automated test should only be done when the result of the test is clear-cut to a machine.  The reason is simple: mistake in law can be incredibly costly.

Testing is just one element of the software quality pursuit.  Tracking application code in an organized manner is the next piece of the puzzle.

B. Source Code Repository

As an introduction to the legal profession, a source code repository is fundamentally the same type of product as a document management system (DMS) like IMANAGE or NetDocuments.    A DMS stores documents like legal briefs, for example; a source code management system stores application source code.

Attorneys regularly use a DMS to check out/check-in documents he/she is working on, store different revisions of a document, or check audit logs to check who has edited, browsed, downloaded, or printed a document during the timeline of a document. The value of this type of system is obvious to the careful lawyer, as it is used to avoid mistakes, eradicate ambiguity, and if necessary, correct mistakes.

A system named Git is, in our experience, the predominant source code management system in the software industry.  In short, it allows developers like John Hall to do things like check out code, merge changes back into the code base, and maintain revision and restoration history.  It’s an incredibly valuable tool — just like an IMANAGE or NetDocuments with legal work product– to understand change history and to restore to prior versions if/when needed.

Will attorneys ever need to use Git?    Certainly not.  But should the professional understand that the tool exists and insist on teams developing critical software for their clients to use a tool like this?  Absolutely.

Developers working without a control system for code is paramount to attorneys storing all of their client documents on a local hard drive.  The risk of practices like that — accidental deletion, limited access to shared work product, inability to track revision history — are far too great.

Refining areas like testing and code management are important functions, not unlike the development of strong legal research or legal documents.  Pulling it all together is the next level activity.  Some tips for enabling strong project team communication come next.

C. The Importance Of Organization And Feedback 

In Matt’s view, raising the bar with software testing comes down to two elements. First is the test plan.  If you are to properly validate the functionality of a system, a formalized test plan must be put in place. A test plan is a key to the success of new software, for it ensures that the functionality will be tested fully and completely to ensure operational effectiveness.

The second key element of testing and tying together all of the processes and documenting issues.  Matt has learned using a system like Git helps us properly store the many issues we have to work on.  It is both convenient and efficient to track issues and test scripts in the same location as our main system code.

Is this all that different from processes in place with legal? No, not really.  It’s quite common within a law firm for one paralegal/attorney to work on something and pass it along to others for a quality check.  Technologists are reviewing code written by developers, lawyers are reviewing legal work product. Conceptually, these are similar concepts.

More specifically, Git allows us to track multiple issues related to any software defect, by creating what are called “labels” for each issue. Matt can capture and attach screenshots of the problem, collaborate via inline conversations associated with each defect, and as a team work together to close issues.  Combining our issue tracking with a source code repository is beneficial much like linking together a case management system, document management systems, and time/billing entry system–the goal is to help the legal practitioner (or, in our case, the developer) be more efficient.

Of course, not all law firms or corporate law departments “build their own software”. In fact, most purchase software from professional vendors.  We’ll now pivot and examine some of the key issues when procuring software in the marketplace.

II. Software Standards And Ecosystems

In the law, there are several components comprising high-quality legal work product. This includes excellent researchers, skilled writers with strong practice knowledge, attorneys with knowledge of relevant case law and poised trial advocates.

In this section, we’ll describe some of the legal technology standards and ecosystems which are contributory to software quality and value.  These include many standards interwoven into legal tech (both present and future), an overview of some common marketplaces for acquiring legal technology, the emporiums (or marketplaces) listing various software offerings.

It is important to note that the “ecosystems” and “emporiums” are not individual systems per se.  Details on provisioning individual systems are covered in Section III.

A. The Value Of Standards

Ken spent the first portion of his business career in Big Pharma (Bristol-Myers Squibb),  which drove home to him the value of standards when developing digital solutions.

With BMS, Ken worked on projects to connect the Company to our customers, such as developing better ways to communicate about product flow was the order of the day.  We decided to adopt data standards by organizations like the American National Standards Institute (ANSI) and United Nations (EDIFACT) to standardize transactions like an order forecast, the order itself, shipping confirmation, and invoice.  This way, if we, for example, built an interface with a customer like CVS, it could be easily reused with another customer like Walgreens or Walmart.

Pivoting to our field, legal operations, how can those concepts be applied?  Well, one great example of ongoing usage is the LEDES billing initiative.  This has greatly helped the industry by standardizing billing between law firms and clients.

Those flying the flag of legal innovation on the bridge of the large ships, such as Thomson Reuters, can see many other opportunities on the horizon.  See, e.g., Post 151 (Carlos Gámez  discussing  Legal Evolution).  Standards aiming at common methods of exchanging matter updates is one great example.   The development of contracts, SEC filings, and other legal oriented transactions via common approaches also are in play and will continue to show increased adoption levels.  Organizations like the SALI Alliance and OASIS, amongst others, are key drivers in the move to interoperability.  It is our belief that the development of legal directories and the integration of legal technology into more mainstream corporate technologies like ERP and CRM will help our industry gain considerable efficiencies in the near-term.

It is important to note that standards don’t only relate to interoperability and communications protocols.  The manner in which software is constructed and how developers collaborate together is also like a mine rich with natural resources–technologists can pull something out that enormous commercial value for a specific use case.  The effort-reward ratio can be staggering.

As John Hall notes, Embracing technical standards ([such as] HTTP, JSON, XML, etc.) not only helps insure software service interoperability, but it can also potentially reduce software development time.  Much high quality, production-tested, open-source libraries are available (Github) for managing standards-based communications (HTTP) and data (JSON, XML).”

Finally, embracing standards isn’t only beneficial for quality and efficient purposes, but doing so can also lead to business opportunities.   As an example, several years ago, Xerdict constructed some LEDES billing capability (the common 1998B standard).  Over time, we built a function to accept invoices and audit invoices for a client.   In turn, because of this capability, we were able to help the same client with some invoice collection and reporting functionality.  So, you never know how work adopting industry standards can help your practice (productivity, quality, or business development).

Even when standards are not uniform across the industry, as now in legal, nascent standards are often beneficial in legal work product. Consider the contract process (which I am not an expert on), for example.  Most lawyers I’ve worked with review contracts ensuring certain components are incorporated (confidentiality, security protocols, venue for dispute resolution, pricing, term, service level agreements, etc.).  Even if these are not formalized industry standards, they still are standards in some sense and deliver value to the process, as all contracts are evaluated in a like manner by lawyers. If lawyers’ implicit standards are helpful, imagine what might be accomplished by adopting explicit standards.  Certainly this would create more work for legal technologists and enable lawyers to perform more legal work per unit of time.

The key point here is the integration of standards into legal software helps improve quality. Next come some tips on how to identify “best in breed” applications within common marketplaces.

B. Enterprise/Cloud Marketplaces

This describes software deployed in B2B versions of marketplaces like the cell phone app stores we use in our personal lives (Google Play, Apple App Store).  Such marketplaces exist in enterprise software company repositories offered by cloud-based SaaS software such as Amazon Web Services, Salesforce, and Oracle. See also Post 108 (Ken describing this evolution, which has lead to the power Platform as a Subscription (PaaS) model).

One advantage of deployments in these ecosystems is the various vetting (application standards, security, etc.) that is required to deploy within the respective enterprise ecosystems.  Other compelling value pillars include employee connectivity (e.g. Salesforce connecting the marketing department to the corporate legal function as part of a regular, predictable workflow) or linking employees collaborating on legal activities, perhaps things like opening a new facility or finalizing a licensing agreement, which happen to use systems with the same underlying technology (e.g. an Oracle database).

Perhaps taking a look at a practical, real-life example can add context here.  Brooklyn, New York-based Litify, offers a legal case management platform that enables law firms to intelligently manage every part of their business from one integrated practice management system.  Pam Wickersham, Litify VP of Product and Engineering, observes:

Prior to being accepted as a Salesforce AppExchange partner, software applications must pass a rigorous security and compliance review. What this means is that every product in the Salesforce ecosystem has met the gold standard for security and trustworthiness: applications have been thoroughly tested to find any potential security vulnerabilities that may put customer data at risk,” said Pam Wickersham, Litify VP of Product and Engineering.

Likewise, partnerships with Salesforce is nudging the legal industry trends towards working towards common standards, process automation, and high-level business intelligence reporting tactics.  Wickersham continues:

The beauty of the AppExchange is that it helps Salesforce users amplify the value of their existing platform. Salesforce is known for its extensibility: users can integrate their favorite third-party solutions and customize their instance to meet the specific needs of their business. By integrating AppExchange solutions into their Salesforce platform, they are able to greater automate routine processes, access more comprehensive and accurate analytics, and create a more efficient and user-friendly experience for their employees. At Litify, we know that our users will only drive more value from our software if they are fully embracing the power of the Salesforce ecosystem by integrating all of their third-party tools into the platform.

Clearly, the road travelled by Litify, and others aligning with market leaders in the ERP (Enterprise Resource Planning) and CRM (Customer Relationship Management) space, raises the bar for software aimed at the legal vertical.

Sometimes, however, software is not purchased within the friendly confines of major enterprise players.  Legal marketplaces might be considered the “Yellow Pages” of the legal technology industry.  In these locations, one can find various types of players, both large and small. Here’s a look at a few collections of legal software providers in the industry.

C. Legal Emporiums

Increasingly, legal marketplaces are coming to fruition.  One example is the recently announced Thomson Reuters Marketplace, which presents new offerings to attempt to continue drive to deliver interoperability and deeper integration with one of their product offerings and others.  Certain legal software companies like Clio offer something a touch different, a set of applications within their own App Store.

Brian Zubert, the Director, Ecosystem Development of Thomson Reuters, opines on the marketplace concept, looking at both the past and present:

Investment in LegalTech has grown substantially in recent years, and so too have the number of solutions and services available. Although law firms and corporate legal departments have more choices than ever, the reality is that there are more options available than purchasing budget, procurement capacity, integration capability, rollout management, and investment needed to drive meaningful user adoption. 2020 magnified the operating constraints and competing for technical priorities. We launched the Thomson Reuters Marketplace to reduce the challenges of discovery and narrow the field to solutions that are known to work well with existing technology investments the firm or organization has already made.

Zubert describing some of the tactical steps necessary to construct a useful marketplace integrating best practices in standards and interoperability as follows.

Meeting the needs of firms, legal departments, technology companies, vendors, and more, requires a team effort. Most solution providers are doing everything they can to meet security and procurement requirements; many companies, including Thomson Reuters, are publishing more APIs as well as defining and adopting open standards like LEDES and SALI; and law firms and corporate legal departments are prioritizing integration and interoperability. At the end of the day, all this heavy lifting technical work is all in pursuit of a joint ambition: getting legal work done simply, efficiently, and accurately.

Increasingly, interoperability and the development of standards is considered a key opportunity to raise the bar within legal tech.  More specifically, because legal tech has a large number of smaller software companies and approaches that are all vying for increased market shares–as compared to the CRM space, which is dominated by Goliath Salesforce–standards have the potential to play a more significant role.

Given this blueprint, the opportunity for standards such as the Legal Matter Standard Specification (LMSS) put forward by SALI or the OASIS XML based contract standard is considerable.  This is because, the more legal tech vendors adopt and require such standards (not unlike ANSI and EDIFACT approaches in other industries), the more efficient data transfers will be between law firms and their clients.  To the extent legal marketplaces in places like Thomson Reuters or Clio become advocates for such approaches, the industry greatly benefits.

Moreover, we note there are certain entities, like the Legaltech Hub, which are designed to provide comprehensive directories of legal technology resources.  While these are not specifically contributory to core software quality in the sense that they do not vet products, they do add value in this area.  More precisely, resources that provide organized views of software products, coupled with access to skilled technology consultants, are an important component of software quality. This is because, naturally, a component of software quality and value is the service element of being able to customize and support these tools.

At this point, understanding we’ve covered some best practices for building software and strategies for identifying some software options, let’s narrow our field of vision a bit, shifting the discussion to explaining some of the key architectural backbones used in the delivery of specific applications to corporate legal departments and law firms alike.

III. Deploying Individual Legal Applications

One thing lawyers and technologists have in common is varying the scope of our work.  Sometimes attorneys are managing a group of matters, other times they are more narrowly working on a single document, attending a deposition, or representing a client at a court conference.

Section III is the technologist’s version of this more defined activity. It talks to different methods of provisioning individual systems.  Some examples of a single legal system are law firms implementing a practice management system, document management system, or time entry and billing system.

In this section, we’ll first discuss spinning up cloud-based legal software systems in essentially a public internet area (Software as a Service or SaaS).   We’ll then pivot into building tools within large enterprise software providers like Oracle, AWS or Microsoft. We’ll conclude with a quick summary of the private cloud/container option using Reynen Court as an example.

A. Cloud-Based Vendor Legal Software

This category, known as Software as a Service (SaaS), is probably the most prevalent and best understood offering in the cloud software category within the legal profession.  See Post 108 (discussing evolution of legal industry technology). Essentially, it describes a collection of software offerings running in-the-cloud (not on-premise) in functional areas like practice and litigation management, document management, financial time and billing vendors and others.

Some of the key strategies in play to improve software quality and operational standards in this space include activities like vendor surveys and reviews to ensure appropriate security procedures are in place, joining user groups to be part of the process for defining new release feature sets, and mastering each vendor’s support arm so that issues can be quickly identified and resolved.  Selecting software providers who are actively involved in seeking certification within the ISO/IEC 27000 family is another great way to be sure a software partner is maintaining secure and solid operations.

For the most part, legal operations and technology professionals are well attuned to these techniques, so we will omit detailed descriptions of these activities.  But it’s fair to summarize this by saying partnering with your SaaS software providers will help law firms and corporate law departments enjoy a better computing experience.

Sometimes, using the cloud can be approached a bit differently.  Next we’ll take a look at some of the advantages of running legal applications within the architecture of what some might refer to as “Big Tech”

B. Cloud Architecture Applications

Arguably, there is considerable value in running legal applications in enterprise-level hosting companies such as the Oracle Cloud Infrastructure, Amazon Web Services, and other similar offerings.

Some of the value propositions in this space are the same as SaaS providers, benefits like round-the-clock support and access to advanced product offerings like the Oracle Autonomous Database.  For those of us in the industry developing our own software products, as Matt and I do with our product line at Tanenbaum Keale,  it is great to know there are approaches in place to offer turnkey fully patched databases and secure virtual machine environments.

The words of Leo Leung, Senior Director, Product and Strategy, Oracle Cloud Infrastructure, appropriately convey the value of enterprise providers for legal tech:

Oracle Cloud Infrastructure is specifically designed to provide the performance predictability, secure-by-design security, and governance required to support mission-critical, performance-intensive workloads. Oracle Cloud Infrastructure is also the foundation for services containers, microservices, and blockchain, and underpins both our internal workloads and products such as Oracle Autonomous Database.

Security is another area where enterprise vendors provide superior solutions. Leung continues:

Oracle built on our decades of experience securing data and applications with a security-first approach that utilizes built-in tenant isolation, least privilege access, encryption, internal-threat detection, and highly automated threat remediation. Oracle’s infrastructure isolates compute and network resources to help ensure that your personal data and traffic are shielded from other users.

Benefits like these in areas like scalability and security make great strides towards improving software quality.

To wrap up this section, we’ll take a look at the last emerging option in the field, that being the private cloud.

C. Private Cloud / Containerization

Reynen Court is a legal tech platform that aims to be a centralized “app store” for a host of legal tech vendors, relying on concepts like configuring private clouds for each client, a technology known as Kubernetes, and the concepts of containerization.

Rather than Matt and Ken attempting to provide an admittedly high-level description of their approach, we decided to engage with an expert.  Christian Lang, Head of Strategy of Reynen Court, offers the following thoughts describing the benefits of their unique offering to their clients.

Containerization and the cloud-native software paradigm confer significant benefits on enterprises managing a complex and constantly evolving tech stack. Not only do they offer more efficient, resilient, and nimbly scalable applications, but for security-focused enterprises (like law firms and departments), they offer extraordinary data-governance benefits.

With the right platform and container orchestration capabilities, legal enterprises no longer have to choose between the clear benefits of cloud computing and the hands-on control and security of on-premises architecture. Containerized apps can be made fully portable, meaning you can run those applications anywhere–including on infrastructure under your direct control (e.g., a data center or virtual private cloud). This means that, to access modern cloud applications, you no longer need to send your data out to the app (and its vendor-controlled infrastructure); you can bring the app TO your data. For legal enterprises navigating incredibly complex waters around data protection, governance, and sovereignty, that flexibility and control are transformative.”

Lang continues, providing the following thoughts on the value propositions to the software providers on the Reynen Court platform.

The portable, cloud-native application paradigm is equally attractive to application vendors. From a single, state-of-the-art code base, they can service any customer, anywhere, no matter where that customer needs to run the application–from a multi-tenant SaaS environment, to a virtual private cloud, to a proprietary data center. All the vendor needs is a portable, containerized application that plugs into the standard application deployment and management tooling used by the buyer.

The core function of the Reynen Court platform is to give buyers those standard tools and to help vendors deliver their applications in a compatible way–essentially creating a marketplace that reinforces mutually beneficial standards while driving transaction costs down to nothing. Particularly when coupled with a Solution Store that can take the procurement exercise from months to minutes and a data hub that can help applications plug-and-play with key systems and sources of truth within the enterprise, this sort of digital platformization experience can bring revolutionary speed, security, and strategic management capabilities to the technology operations of legal enterprises.

From the Apple App Store and Google Play Store in the consumer space, we’ve seen over the last dozen years just how transformative true digital platformization can be in fostering and supporting path-breaking technologies. Thanks to the maturation of the Kubernetes ecosystem, we now have the ability to bring that same technology-consumption experience and its innovation engine to enterprise legal.

As Lang describes, Reynen Court is a distinctive offering, working within private cloud environments to provide tangible benefits to their clients, most notably in advanced security, software licensing administration, and the convenience of an “App Store” like interface for simplified deployment.  It’s our expectation that approaches of this nature will continue to make inroads in our industry,


Our family just bought a new vehicle.  As one goes through that process, of course, cars with voice-activated technology, automated parking assist, and thirteen speaker stereo systems are really nice.  But if the engine doesn’t run well or the ride is bumpy, in the end, no one’s going to be happy.

As it relates to legal software, understand there is truly a myriad of options out there. It can all be quite dizzying for a general legal practitioner to soak in.  While we hope this piece is a useful overview of the various options, admittedly, it only goes so deep.

That being said, we suggest, in addition to evaluating features and functionality, a key takeaway of this post is surely to suggest that it is worth your time to peek under the hood of products your legal operations team is bringing into your shop so you can have a discussion about how technology is dovetailing with your organization’s long-run business imperatives. Through this process, your legal technologist can aid you and grabbing a lot of low-hanging fruit that the less curious are ignoring.