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Side Letter

Draft Corporate Side Letters in Minutes with AI

12 minutes with CaseMark

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1. Add your email so we know where to send the result.

2. Upload the files you want analyzed.

3. Run the workflow and we'll take it from there.

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Workflow

Side Letter

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Workflow

Side Letter

Overview

Drafting side letters manually requires extensive review of main agreements, research into jurisdiction-specific requirements, and careful attention to formatting and enforceability standards. Attorneys spend hours cross-referencing clauses, researching best practices across multiple legal databases, and ensuring consistency with the primary contract—all while billing clients for time-consuming administrative work.

Drafting side letters requires meticulous analysis of primary agreements, precise cross-referencing, and careful attention to avoid conflicts or unintended modifications. Manual drafting is time-consuming, often taking 4-5 hours per document, and carries risks of inconsistencies, missing provisions, or inadequate integration with the underlying contract.

CaseMark analyzes your primary agreement and generates comprehensive, legally enforceable side letters in minutes. Our AI ensures perfect alignment with the main contract, accurate cross-references, and all essential provisions while maintaining the highest standards of corporate legal drafting.

How it works

  1. 1. Upload your documents

  2. 2. AI analyzes and extracts key information

  3. 3. Review and customize the generated content

  4. 4. Export in your preferred format (DOCX, PDF)

What you get

  • Header and Parties

  • Recitals

  • Specific Terms

  • Governing Law and Miscellaneous

  • Signatures

What it handles

  • Header and Parties

  • Recitals

  • Specific Terms

  • Governing Law and Miscellaneous

  • Signatures

Required documents

  • Primary Agreement

    The main contract or agreement that the side letter will supplement (e.g., investment agreement, employment contract, commercial agreement)

    PDF, DOCX, DOC

Supporting documents

  • Prior Amendments or Side Letters

    Any existing amendments or side letters to the primary agreement that may impact the current drafting

    PDF, DOCX, DOC

  • Board Resolutions or Approvals

    Corporate authorizations or board approvals required for executing the side letter

    PDF, DOCX, DOC

  • Term Sheet or Business Terms

    Document outlining the specific modifications, exceptions, or additional terms to be included in the side letter

    PDF, DOCX, DOC, XLSX

Why teams use it

Generate complete side letters in 8 minutes vs. 3.5 hours manually

Automatic analysis of main agreements to ensure consistency and proper references

AI-powered research of jurisdiction-specific requirements and enforceability standards

Professional formatting with standard clauses from authoritative legal sources

Reduce drafting costs while maintaining quality and compliance

Questions

What is a side letter and when should I use one instead of an amendment?

A side letter is a supplementary agreement that modifies, clarifies, or adds provisions to a primary contract without formally amending it. Side letters are ideal when you need to address specific concerns for particular parties, establish confidential arrangements, or make targeted modifications while preserving the structure of the main agreement. They're commonly used in venture capital, private equity, and commercial transactions when parties need flexibility without triggering formal amendment procedures or broad disclosure requirements.

Does CaseMark ensure the side letter doesn't conflict with my primary agreement?

Yes, CaseMark analyzes your primary agreement to identify relevant terms, amendment provisions, and potential conflicts before drafting. The system generates precise cross-references to specific sections and includes clear hierarchy provisions establishing that the side letter controls for the matters it addresses. CaseMark also flags any restrictions on modifications or requirements for board approval found in the primary agreement.

Can I use this for confidential side letters in investment transactions?

Absolutely. CaseMark includes robust confidentiality provisions when drafting side letters for venture capital and private equity transactions. The system can generate terms specifying who may access the side letter, disclosure restrictions, and remedies for unauthorized disclosure. This is particularly valuable for side letters granting special rights, most-favored-nation provisions, or other terms that investors prefer to keep confidential from other stakeholders.

How does CaseMark handle governing law and dispute resolution in side letters?

CaseMark automatically mirrors the choice of law and dispute resolution provisions from your primary agreement to ensure consistent interpretation and avoid conflicts. The system includes comprehensive governing law clauses, arbitration or litigation provisions matching the main contract, and all necessary boilerplate tailored to your jurisdiction. If your transaction requires different dispute resolution mechanisms for the side letter, you can specify those requirements and CaseMark will draft accordingly.

What information do I need to provide to generate a side letter?

You need to upload the primary agreement that the side letter will supplement and provide information about the specific modifications, clarifications, or additional terms you want to include. CaseMark will prompt you for details about the business purpose, which parties are involved, any confidentiality requirements, and the duration of the side letter's terms. The more context you provide about your commercial objectives, the more precisely CaseMark can tailor the document to your needs.

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