Today we’re announcing a new AI Playbook Library inside SimpleAI, giving legal teams immediate access to 50+ expert-developed and data-informed negotiation standards directly within Microsoft Word. The playbooks are powered by Law Insider Standards, led by Electra Japonas, SimpleDocs’ Chief Legal Officer, and creator of the oneNDA and oneDPA initiatives.

Each AI Playbook in the library is fully configurable, including fallback positions, custom comments, and internal negotiation notes.

“Most in-house legal teams don’t have comprehensive playbook libraries, and almost none have playbooks that are AI-ready,” said Preston Clark, CEO of SimpleDocs and a former corporate attorney. “This release gives legal teams an AI-enabled, expert-developed starting point that can be easily tailored to their own negotiation requirements.”

No playbook? No problem.

The AI Playbook Library is fully native to SimpleAI, enabling the add-in to instantly produce AI-generated redlines inside Microsoft Word. Instead of generating generic markups, SimpleAI draws on structured, expert-developed playbooks—each informed by real contract data—to surface issues, propose revisions, and generate redlines aligned with best practices and internal negotiation positions.

The AI Playbook Library spans more than 50 of the most commonly negotiated commercial agreements, including:

• NDAs: Mutual; unilateral (discloser- or recipient-favourable); M&A NDAs (buyer-, seller-, and JV-favourable)
  
• MSAs: Buy-side and sell-side
  
• DPAs: Controller–Processor; Controller–Controller; Processor–Sub-processor
  
• SaaS and Licensing Agreements
  
• Professional Services & Consulting Agreements
  
• Channel Partner, Reseller & OEM Agreements
  
• Supply of Goods Agreements (buy/sell-side)
  
• White-Label / OEM Agreements (buy/sell-side)
  
• Vendor Agreements
  
• Contractor Agreements
  
• Royalty / Revenue Share Agreements
  
• Commercial Terms, PO Terms & Facility/Lease Agreements
  
• SAFE / Convertible Loan Note Agreements
  
• …and dozens more across procurement, data protection, IP, and commercial operations.
  

Fully Configurable AI Playbooks

Every AI Playbook in SimpleAI is fully configurable, giving legal teams precise control over how negotiation standards are applied inside Microsoft Word. Playbooks can be tailored to reflect internal policies, risk tolerance, industry nuances, and departmental preferences.

Teams can customize:

• Fallback positions,
• Issue-specific comments, 
• Internal negotiation notes,
• Governance controls and sharing permissions
  
  

We also provide a growing library of Playbook Tutorials to help teams build and configure their negotiation standards over time.

From oneNDA to Law Insider Standards

This release builds on the legacy of oneNDA, the open-source mutual NDA launched in 2021 that became the world’s most widely adopted NDA standard. When Law Insider acquired oneNDA in 2024, the vision expanded to create the most comprehensive, community-driven catalog of contract standards available.

Led by Electra Japonas—co-founder of oneNDA and now Chief Legal Officer at Law Insider—the Law Insider Standards initiative evolved into a peer-reviewed library of playbooks, templates, and negotiation frameworks informed by in-house counsel, operators, and subject-matter experts across industries.

These standards are now directly embedded in SimpleAI, including Law Insider Standard Templates such as oneSaaS, oneDPA, and more—offering users rapid access to compliant, configurable versions of globally recognized templates inside Microsoft Word.

Context in Contracting

As Legal AI adoption accelerates, we are distinguishing ourselves by grounding our tools in real-world precedent rather than generic language models. SimpleAI relies on authoritative contract data, community-led standards, internal team rules, and market insights to produce AI suggestions that legal teams can trust.

Strategic Acquisition of Law Insider 

In September 2025, SimpleDocs acquired Law Insider, expanding the depth of precedent and context available within our Legal AI tools:

• 20M+ contract clauses from the world’s largest public contract database
• Open-standard initiatives including oneNDA, oneDPA, and oneSaaS
• Market-level benchmarking of clause prevalence and negotiation patterns

Law Insider gives SimpleAI a uniquely contextual understanding of contract language—enabling it to recognize clause patterns, evaluate market norms, and propose revisions that reflect both expert guidance and real-world frequency.

“General-purpose AI is fast, but legal teams need structured Legal AI tools they can trust,” said Clark. “By embedding Law Insider Standards into SimpleAI, we’re giving teams a practical layer of expert-developed, data-informed guidance that improves not just speed, but judgment.”

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FAQ

Which plan includes the AI Playbook Library?

The AI Playbook Library is included in the SimpleAI Base Plan, available exclusively through the SimpleDocs and Law Insider websites. Pricing begins at $159 per user per month, with volume discounted licensing available.

Do you offer free trials?

Start a FREE 14-day trial by booking a demo today:
👉 https://simpledocs.com/book-demo

Do I need my own playbooks to use SimpleAI?

No. SimpleAI includes 50+ expert-developed, data-informed playbooks that can be built and configured directly within Microsoft Word. These playbooks can be used as-is or customized to match your internal preferences.

Does SimpleAI also support fully customized playbooks based on existing playbook documentation?

Yes—SimpleAI Pro includes custom playbook implementation with dedicated support and live training from our Legal Engineering team. SimpleAI Pro is available for $249 per user, per month (3 license minimum).    

Does SimpleAI use our confidential data to train AI models?

No. SimpleDocs does not use customer data, documents, or playbooks to train underlying AI models. Your data remains isolated and encrypted. See the SimpleDocs Trust Center for details.

What types of agreements are supported in the AI Playbook Library?

More than 50 contract types across commercial, procurement, sales, data, IP, and finance, including NDAs, MSAs, DPAs, SaaS, Licensing, Services, Vendor, and Revenue Share agreements. New playbooks are added monthly. A full list of the AI Playbook Library is available here

How fast can we get started?

Most teams are live within a week:

1. Complete InfoSec due diligence (if required)
2. Install SimpleAI (Instructions here)
3. Select your first playbook
4. Run your first contract review
5. Customize as needed

Enterprise onboarding packages and POCs are available for larger deployments.

Is SimpleAI suitable for law firms?

Yes. Law firms use SimpleAI to accelerate associate review, standardize partner guidance, build firm-wide negotiation playbooks, and deliver faster, more consistent outcomes for clients.

What security certifications does SimpleDocs have?

SimpleDocs is:

• SOC 2 Type II certified
• GDPR compliant
• TX-RAMP Certified
• Hosted in secure, enterprise-grade cloud environments
• Equipped with role-based access controls and audit logging (via SSO)

Security documentation is available via the SimpleDocs Trust Center or through an InfoSec Review Call.

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