Choosing Case Management Software: A Strategic Guide for Mid-Size and Enterprise Law Firms

Law firm operations are no longer just about managing cases—they’re about managing complexity. For mid-size and enterprise law firms, the decision to implement or upgrade Case Management (CM) software impacts attorneys, staff, clients, and ultimately, your bottom line. 

The right platform creates efficiencies by having a “single pane of glass” view of your matters. The wrong one frustrates your teams and leads to costly do-overs. You’ve heard the horror stories of botched implementations. 

If your firm is evaluating CM software in 2025, here are the key considerations to guide your decision-making. 

1. Prefab or Custom? 

Some software platforms are one-trick ponies. If you are their exact target firm, it could work. You won’t be able to customize but it will be a good value. However, if you are outside that software’s area of expertise, you’ll spend hundreds of hours having your team shave the corners off of square pegs. It is unfortunate to watch firms try to save $10,000 in licensing costs only to pay triple in lost productivity. 

Most CMs don’t offer AI time entry aids (yet). Even once they do, they may not have the sophistication of a dedicated product. If AI-assisted time entry is important to you, find a solution you love and integrate it into your CM.

Ask yourself: 

• Do we need a platform that can handle multiple matter types and billing models? 
• Am I okay with using an out-of-the-box workflow or do we have a process we want to see built? 

The best systems don’t force standardization; they enable scalable flexibility. 

2. Don’t Overlook Billing and Time Tracking  

Mid-size and large firms often lose significant revenue through unbilled time or inefficient invoicing processes. Your CM software should make it as easy as possible for attorneys to capture their time—accurately and with minimal disruption. 

Look for: 

• Passive time tracking tools that record work in the background 
• Automated pre-bills and invoice generation based on custom billing arrangements 
• Built-in compliance with client guidelines and LEDES/UTBMS formats 

Better timekeeping means better financial performance and happier clients. 

3. Enhance the Client Experience 

As legal services become more client-centric, firms are being judged not just on outcomes, but on the experience they provide. Your CM platform should support proactive communication, transparency, and responsiveness, especially for clients used to digital-first services in other industries. 

What to look for: 

• Some software platforms have this functionality built in. This is more cost effective, but sometimes less flexible. 
• Other vendors will have an integration ecosystem that affords more options with more power and flexibility, but at a cost. 
• Avoid software with no capabilities or that require your team to do double entry. 

When clients feel informed and in control, they’re more likely to trust—and stick with—your firm. 

4. Make Security and Compliance Non-Negotiables 

Enterprise law firm clients are demanding more assurance around how their data is handled. Whether you’re managing sensitive IP, health records, or financial data, your case management software needs to meet the highest standards of security. 

You’ll want: 

• End-to-end encryption (in transit and at rest) 
• Granular user permissions and audit trails 
• SSO, which can make your firm more phishing resistant 

Ask product vendors how they handle data residency, breach protocols, and penetration testing. It’s not just an IT question—it’s a client trust issue. 

5. Long-Term Vision: Can It Scale with You? 

What will your firm look like in three years? Pick a Case Management software for both your today and your tomorrow. Whether you’re expanding into new jurisdictions, adding new teams, or merging with another firm, your CM solution should scale without disruption. If you hope to be acquired, the value of your firm will increase if you have accurate, organized data that can be merged in. 

Ask: 

• How easily can we onboard new users, matters, or practice areas? 
• What does their product roadmap look like—and are they innovating in ways that align with our vision? 

Choose a partner, not just a product. 

6. Look for Smart Integrations (Avoid Creating Another Silo) 

Mid-size and large firms usually already have robust tech stacks—document management systems, CRM platforms, accounting software, e-discovery tools. Your CM software shouldn’t operate in a vacuum. 

Look for: 

• Native integrations with tools your attorneys already use (like Outlook, NetDocuments, iManage, or DocuSign) 
• Open APIs for more advanced connections 
• Easy data migration and export options 

Tech that plays well with others reduces context switching and improves adoption across the board. 

7. Prioritize Adoption and User Experience 

At the enterprise level, poor user experience can torpedo even the most powerful platform. If it’s clunky, hard to navigate, or too complex, your attorneys won’t use it—and you won’t get the return you’re expecting. 

Consider: 

• How intuitive is the user interface, even for non-technical users? 
• Are mobile and tablet options available for on-the-go attorneys? 
• What kind of onboarding, training, and ongoing support is offered? 

User adoption isn’t a training problem—it’s a design and experience challenge. 

Final Word: Technology Is a Strategic Asset—Treat It Like One 

Choosing the right Case Management software isn’t just about streamlining operations. It’s about aligning your technology with your firm’s broader business objectives—client service, profitability, growth, and innovation. 

In 2025 and beyond, firms that invest in the right platforms will have a clear advantage. They’ll move faster, operate smarter, and deliver better outcomes for clients and teams alike. 

Take your time, ask layered questions, look beyond the features list, and evaluate how the solution will fit into the way your firm practices law. 

If your firm is looking for guidance in navigating the selection and delivery journey, our team is here to help. Contact us today to find out more!