ContractWorks vs Outlaw Comparison: Reviews, Features, Pricing & Alternatives in 2026

Detailed side-by-side comparison to help you choose the right solution for your team

Updated Apr 2026 8 min read

ContractWorks

0.0 (0 reviews)

ContractWorks is a contract management software providing a centralized repository with automated alerts, AI-driven data extraction, and integrated electronic signatures to help you streamline your entire legal agreement lifecycle.

Starting at $700/mo
Free Trial 0 days
VS

Outlaw

0.0 (0 reviews)

Outlaw is a modern contract management platform that streamlines the entire agreement lifecycle from automated drafting and real-time negotiation to integrated e-signatures and searchable digital contract storage.

Starting at --
Free Trial NO FREE TRIAL

Quick Comparison

Feature ContractWorks Outlaw
Website contractworks.com getoutlaw.com
Pricing Model Subscription Custom
Starting Price $700/month Custom Pricing
FREE Trial ✓ 0 days free trial ✘ No free trial
Free Plan ✘ No free plan ✘ No free plan
Product Demo ✓ Request demo here ✓ Request demo here
Deployment saas mobile cloud mobile
Integrations Salesforce SAML SSO DocuSign Salesforce HubSpot Slack Microsoft Teams Google Drive Dropbox Box Zapier
Target Users small-business mid-market small-business mid-market enterprise
Target Industries legal real-estate technology
Customer Count 0 0
Founded Year 2012 2017
Headquarters Santa Barbara, USA New York, USA

Overview

C

ContractWorks

ContractWorks provides a streamlined way for you to take control of your company’s legal agreements without the complexity of traditional enterprise systems. You can set up a secure, searchable repository in minutes, allowing your team to locate any document instantly using advanced OCR technology. By centralizing your contracts, you eliminate the risk of missing critical renewal dates or losing track of high-value obligations across different departments.

The platform automates the tedious parts of contract administration by using AI to extract key dates and terms automatically. You also get built-in electronic signatures, so you can send, sign, and store documents in one continuous workflow. It is designed specifically for in-house legal teams and small-to-mid-sized businesses that need a quick-to-implement solution that balances powerful reporting with an incredibly simple user interface.

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Outlaw

Outlaw is a contract management platform designed to help you move deals from draft to done faster. Instead of juggling static Word docs and endless email threads, you get a centralized workspace where you can build dynamic templates, negotiate terms in real-time, and track every version of an agreement. It eliminates the friction of manual data entry and fragmented communication by keeping all stakeholders on the same page throughout the entire contract lifecycle.

You can automate your document generation using a powerful template engine that ensures compliance while saving hours of manual work. The platform is built for teams that need to scale their legal operations without adding headcount, offering a clean interface that both your legal team and sales reps will actually enjoy using. It provides deep visibility into your contract pipeline so you never miss a renewal or a critical deadline again.

Overview

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ContractWorks Features

  • AI Data Extraction Save hours of manual entry by letting AI automatically identify and extract key dates and clauses from your uploaded documents.
  • Smart Notifications Set automated email alerts for upcoming milestone dates and renewals so you never miss a contract deadline again.
  • Integrated E-Signatures Send documents for signature directly from the platform and watch them automatically file themselves once the signing is complete.
  • Advanced OCR Search Find exactly what you need across your entire library by searching for specific words or phrases within scanned PDF images.
  • Custom Reporting Generate detailed reports on contract status and value in seconds to share high-level insights with your executive team.
  • Secure Permissioning Control exactly who can view or edit specific folders with granular access levels to keep sensitive legal data protected.
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Outlaw Features

  • Dynamic Templates. Turn your standard agreements into smart templates that you can populate instantly with deal-specific data.
  • Real-Time Negotiation. Negotiate terms directly within the document with your counterparts to reach an agreement faster without versioning issues.
  • Integrated E-Signatures. Collect legally binding signatures the moment a deal is reached without ever leaving the platform.
  • Automated Workflows. Set up custom approval chains so the right people see the right documents at the right time.
  • Contract Repository. Store all your executed agreements in a searchable digital vault to find any clause or date in seconds.
  • Activity Tracking. Monitor exactly when recipients open, view, and interact with your contracts to time your follow-ups perfectly.

Pricing Comparison

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ContractWorks Pricing

Standard
$700
  • Up to 2,500 documents
  • Unlimited users
  • 5 free electronic signatures
  • AI-assisted data extraction
  • Automated alerts and notifications
  • Advanced OCR search
O

Outlaw Pricing

Pros & Cons

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ContractWorks

Pros

  • Unlimited user seats prevent unexpected scaling costs
  • Extremely fast implementation compared to enterprise competitors
  • Clean interface requires almost no user training
  • Highly responsive and helpful customer support team

Cons

  • Lacks advanced redlining and drafting tools
  • E-signature limits on lower tiers are restrictive
  • Reporting can feel basic for complex organizations
A

Outlaw

Pros

  • Intuitive interface makes it easy for non-legal users
  • Powerful template engine significantly reduces drafting time
  • Real-time collaboration eliminates confusing email chains
  • Excellent customer support during the implementation phase

Cons

  • Initial template setup requires a learning curve
  • Formatting options can be restrictive for complex layouts
  • Pricing is less transparent than simpler e-signature tools
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