Contracts 365 vs. Icertis

Executive Summary

How Enterprise Legal Teams Evaluate Contract Management Software Systems

Enterprise legal teams evaluate contract management systems based on more than feature availability. Decision criteria typically include long-term governance, audit defensibility, system sustainability, and alignment with enterprise IT standards.

Key evaluation areas include:

• Legal governance and compliance controls
• Reliability and transparency of AI-assisted functionality
• Workflow flexibility balanced against operational complexity
• Security, identity, and document management alignment
• Implementation risk and long-term ownership cost

This comparison reflects those priorities.

Quick Comparison Overview

Legal Governance & Compliance

Both Contracts 365 and Icertis provide enterprise-level governance capabilities designed to support legal oversight and regulatory requirements.

Contracts 365 emphasizes governance through:

• SharePoint-native version control and document history
• Role-based access and approval workflows
• Clear audit trails aligned with Microsoft security models

Icertis supports governance through:

• Highly configurable contract models
• Advanced obligation and compliance frameworks
• Extensive audit and reporting capabilities across large contract portfolios

Both platforms meet enterprise legal governance needs, with differences primarily in how governance is configured and maintained over time.

AI Contract Management Capabilities for Legal Teams

AI capabilities in enterprise legal environments are typically evaluated based on accuracy, explainability, and support for human review, rather than automation alone.

Contracts 365 uses AI to assist with:

• Contract metadata extraction and negotiation
• Contract classification and insights
• Obligation visibility within existing Microsoft tools

Icertis offers AI-driven functionality focused on:

• Advanced contract intelligence
• Obligation tracking across large datasets
• Risk identification within configurable contract models

For enterprise legal teams, the distinction is less about whether AI exists and more about how transparently it supports legal review and defensible decision-making.

Workflow Design & Operational Complexity

Workflow design is often a defining factor for enterprise legal CLM success over time.

Icertis is known for:

• Extensive workflow configurability
• Support for highly complex, global legal processes
• Deep customization aligned to enterprise-specific contract models

This flexibility can be valuable but often requires dedicated legal operations or technical resources to maintain.

Contracts 365 focuses on:

• Structured, repeatable workflows
• Legal control with reduced administrative overhead
• Easier long-term maintenance within Microsoft 365 environments

The trade-off is typically maximum configurability versus sustainable operational simplicity.

Microsoft 365 & Enterprise IT Alignment

Microsoft ecosystem alignment is a key consideration for enterprise legal teams operating within standardized IT environments.

Contracts 365 is designed to operate natively withinMicrosoft 365, including:

• SharePoint as the document system of record
• Microsoft identity, security, and access controls
• Contracts and related data stored within your existing Microsoft tenant

Icertis operates as a standalone enterprise platform with integrations into Microsoft tools, but documents and workflows are managed outside the native SharePoint environment.

For organizations standardized on Microsoft 365, native alignment can reduce system duplication, simplify access controls, and lower long-term operational risk.

Implementation, Ownership & Time to Value

Implementation complexity and ownership expectations vary significantly between the two platforms.

Icertis implementations often involve:

• Longer deployment timelines
• Significant configuration and modeling
• External consulting or system integrator support

Contracts 365 implementations are typically:

• Faster for Microsoft-centric organizations
• More incremental in rollout
• Easier to manage with existing IT and legal ops resources

These differences are often less about platform capability and more about organizational readiness and appetite for complexity.

Which Platform Is the Better Fit for Enterprise Legal Teams?

Contracts 365 is often a strong fit if:

• Your legal team operates primarily within Microsoft 365
• Governance, traceability, and audit-ability are top priorities
• You want predictable rollout and adoption
• Legal operations resources are limited or shared

Icertis may be a better fit if:

• Your organization manages highly complex, global contract structures
• You require deeply customized contract models
• Dedicated legal operations and technical resources are available
• Longer implementation timelines are acceptable

Frequently Asked Questions by Enterprise Legal Teams

Is Contracts 365 suitable for large enterprise legal teams?
Yes. Contracts 365 is used by enterprise legal teams that require governance, auditability, and scalability within Microsoft-based environments.

How does Icertis compare for compliance-heavy organizations?
Icertis is frequently selected by organizations with complex regulatory and contractual modeling requirements.

Can Contracts 365 support multi-entity or regional legal teams?
Yes. Contracts 365 supports structured governance and access controls across business units using Microsoft security frameworks.

How do legal teams typically choose between Contracts 365 and Icertis?
The decision often depends on the balance between required configurability and long-term operational simplicity.

Final Perspective

Both Contracts 365 and Icertis are capable enterprise contract management software systems designed to support legal governance at scale.

The right choice depends on whether your organization prioritizes deep configurability and contract intelligence or operational consistency within Microsoft 365.

To understand how Contracts 365 supports enterprise legal teams, request a demo today.