Why Legal Teams Outgrow Jira: The Checkbox Advantage

Jira works well—until it doesn’t.

In the early stages of building processes and managing requests, Jira may seem like a practical solution. It’s relatively flexible, widely adopted across organizations, and excels in managing workflows—at least for software development and IT.  

However, managing contracts, compliance, and legal intake processes isn’t the same as tracking development sprints. And as legal teams grow, so do their operational complexities, and that’s when it starts to create more work rather than improve efficiency.

Now, if there’s one thing every legal team knows, it’s that time is precious. Spending hours managing fragmented workflows and trying to configure general-use project management software is time not spent on strategy, growth, or protecting the company from risk. That’s why legal teams eventually find themselves asking: “Is there a better way?”

Yes, there is—Checkbox.  

Purpose-built for in-house legal teams, Checkbox’s AI-powered intake and matter management software empowers legal teams with tools that streamline intake, automate workflows, and provide a single source of truth for all legal matters.

Where Jira requires adaptation, Checkbox adapts to you.

In this blog, we’ll explore why legal teams often outgrow Jira, the specific limitations they encounter, and how Checkbox offers a tailored solution that evolves alongside legal departments.

The Problem: Why Legal Teams Hit a Wall with Jira

At first glance, Jira’s flexibility makes it seem like a reasonable choice for legal teams looking to manage incoming requests and track ongoing matters. It’s customizable, widely integrated, and already embedded in many organizations. However, you’ll quickly discover that Jira’s strengths in software development don’t translate well to legal workflows.

1. Jira is Designed for Developers, Not Legal Teams

Jira was designed with software development teams in mind. Its workflows are structured around managing tickets, bugs, and product backlogs—ideal for sprint planning but far from intuitive for legal intake, contract review, and compliance tracking.

• For in-house legal teams, every intake isn’t just a “ticket.” It’s often a multi-faceted request involving stakeholders across departments, multiple documents, and nuanced deadlines.

• Jira’s rigid structure forces legal teams to adapt their processes to the tool, rather than the other way around. This can lead to misaligned workflows and frustration.

2. Fragmented Visibility and Manual Workarounds

As legal operations evolve, managing requests through Jira often leads to overwhelming complexity. Custom fields, labels, and filters are created to mimic legal processes, but they rarely provide the clarity legal teams need.

• Tracking matters across multiple projects can lead to fragmentation, making it difficult to see the full scope of work.

• Teams may resort to manual spreadsheets or additional tools to fill the gaps, further complicating visibility.

3. Limited Reporting and Performance Metrics

One of the biggest pain points for legal teams using Jira is the lack of legal-specific reporting. Legal leadership needs clear insights into matter distribution, turnaround times, and overall team performance.

• Jira’s reports are designed to track development velocity and bug resolution—not legal KPIs like contract turnaround times or risk mitigation efforts.

• Without meaningful analytics, demonstrating legal’s value to the broader organization becomes a challenge.

4. Compliance and Risk Management Limitations

Legal teams deal with sensitive information, privileged communications, and compliance-heavy workflows. Jira’s security model is designed for general IT workflows, which can introduce risk when handling confidential legal data.

• Access controls in Jira are often broad, making it difficult to ensure the right level of confidentiality and data segmentation.

• Audit trails and data retention policies must often be customized, leaving room for error and potential compliance gaps.

Ultimately, while Jira can handle the basics, it wasn’t built to scale with the unique demands of legal teams. As those teams grow and legal operations become more strategic, the limitations of a generalist tool like Jira become roadblocks to efficiency.

How Checkbox Solves Legal-Specific Challenges

Checkbox is a platform built to address the unique challenges that in-house legal teams face.  

While Jira requires constant customization and creative workarounds, Checkbox delivers out-of-the-box capabilities that align with how legal teams actually operate.

Here’s how Checkbox transforms legal operations:

1. Legal-Centric Design

Checkbox was built with legal workflows in mind, offering templates and structures that fit naturally into legal intake, matter management, and compliance processes.

• Pre-built workflows for contract reviews, NDAs, litigation tracking, and compliance audits mean teams can start immediately, without extensive configuration.

• Checkbox’s interface mirrors legal matter management, not development pipelines, ensuring that legal professionals can work comfortably with the platform from the start.

2. Centralized Matter Management

Checkbox consolidates all legal requests, tasks, and matters into a single platform—eliminating the need for multiple project boards or external spreadsheets.

• Unified dashboards provide real-time visibility into all ongoing legal matters, ensuring that no requests or key details go unnoticed.

• Customizable workflows allow teams to manage everything from simple contract approvals to complex litigation matters, all within the same platform.

3. Automated Intake and Triage

Legal teams frequently deal with floods of incoming legal requests, many of which require routing to the appropriate legal professional. Checkbox’s AI-powered intake automates this process, significantly reducing manual effort.

• Dynamic forms collect the necessary information upfront, ensuring each request is complete and routed correctly.

• Automated assignment rules route tasks to the right legal resource based on urgency, request type, or expertise—cutting down on email traffic and workflow bottlenecks.

4. Customization Without Complexity

Unlike Jira, where customization often requires deep technical knowledge, Checkbox allows legal teams to tailor workflows intuitively.

• No-code customization allows legal teams to adapt and adjust workflows on the fly without relying on IT.

• Drag-and-drop workflow builders ensure that even complex processes—such as multi-stage contract negotiations—can be mapped out easily.

5. Enhanced Reporting and Analytics

Checkbox gives legal leaders access to meaningful legal insights. Instead of developer-centric metrics, Checkbox provides detailed analytics on legal KPIs like matter completion rates, workload distribution, and time-to-resolution.

• Real-time reporting highlights bottlenecks, enabling teams to proactively address issues.

• Performance dashboards give Chief Legal Officers (CLOs) and legal ops professionals the data they need to demonstrate legal’s value and secure additional resources.

6. Secure and Compliant by Design

Legal data security is non-negotiable. Checkbox takes this into account by offering robust security features designed to meet the highest compliance standards, ensuring that sensitive information stays protected.

• Granular access controls allow teams to manage who can see and edit specific matters.

• Built-in audit trails ensure full traceability, helping teams maintain compliance with internal and external regulations.

In short, Checkbox empowers legal teams by replacing fragmented workflows with a centralized, automated, and secure solution—one that grows and scales with the evolving demands of legal operations.

Feature Comparison: Checkbox vs. Jira for Legal Teams

The Long-Term Value of Legal-Specific Solutions

The transition from Jira to Checkbox isn’t just about short-term efficiency gains—it’s an investment in the long-term success and scalability of the legal department.  

As legal teams grow and their workloads become more complex, Checkbox evolves alongside them, providing the infrastructure needed to manage increased demand without sacrificing quality or control.

Here’s how Checkbox delivers sustained value over time:

1. Scaling with Organizational Growth

As businesses scale, the volume and complexity of legal matters increase. Checkbox’s flexible architecture allows legal teams to expand their workflows, add new matter types, and manage more requests—without the need for constant reconfiguration.

• Dynamic workflow scaling enables teams to introduce new processes for contract negotiation, litigation, and regulatory compliance as needed.

• Role-based access controls ensure that as new team members are onboarded, they have immediate, secure access to relevant matters and workflows.

• Multi-department collaboration allows legal to work seamlessly with HR, procurement, and finance, ensuring legal processes integrate across the organization.

2. Demonstrating Legal’s Value to Leadership

Through advanced analytics and customizable reports, legal leaders can use Checkbox to highlight operational achievements, communicate value to leadership, and make data-driven decisions.

• Executive-ready dashboards break down legal matter trends, workload distribution, and response times.

• Budget justification reports show how automating legal workflows reduces overhead and accelerates results.

• Forecasting tools help predict future legal needs based on past performance, supporting strategic planning.

3. Empowering Legal Teams to Focus on High-Value Work

By automating routine tasks and streamlining intake, Checkbox frees legal professionals from administrative burdens—allowing them to focus on strategic, high-impact initiatives.

• Automated contract reviews, AI legal chatbots, and self-service portals reduce legal’s involvement in low-risk, high-volume tasks.

• AI-driven triage ensures that the right matters reach the right people, eliminating the need for manual assignment.

• Document automation minimizes repetitive work, accelerating contract drafting, approvals, and renewals.

4. Mitigating Risk and Ensuring Compliance

Checkbox’s built-in compliance features safeguard sensitive legal data and ensure legal teams operate within regulatory frameworks. As new regulations emerge, Checkbox adapts, helping legal departments stay ahead of compliance requirements.

• Automated audit trails track all changes to matters and documents, ensuring full traceability.

• Legal hold capabilities allow teams to manage litigation holds seamlessly without external tools.

• Customizable retention policies help legal teams enforce data governance standards easily.

Overall, Checkbox empowers legal teams to operate more efficiently today while positioning them for growth and success tomorrow. By providing tailored legal solutions, Checkbox not only improves day-to-day workflows but also enhances the legal team’s strategic role within the organization.

The next step? Embrace a platform designed for legal teams.

Book a call with one of our technology consultants today and experience the Checkbox advantage for yourself.