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Venture Capital And Private Equity

Side Letter

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.

Automation ROI

Time savings at a glance

Manual workflow4.5 hoursAverage time your team spends by hand
With CaseMark12 minutesDelivery time with CaseMark automation
EfficiencySave 26.3x time with CaseMark

The Problem

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.

The CaseMark Solution

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.

Key benefits

How CaseMark automations transform your workflow

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

What you'll receive

Header and Parties
Recitals
Specific Terms
Governing Law and Miscellaneous
Signatures

Document requirements

Required

  • Primary Agreement

Optional

  • Prior Amendments or Side Letters
  • Board Resolutions or Approvals
  • Term Sheet or Business Terms

Perfect for

Corporate attorneys handling M&A transactions
Venture capital and private equity lawyers
In-house counsel at investment firms
Corporate development professionals
Startup and emerging company lawyers
Commercial contract attorneys

Also useful for

This workflow is applicable across multiple practice areas and use cases

Side letters are frequently used in M&A transactions to modify purchase agreements, address specific buyer/seller concerns, or document side arrangements between parties without amending the main transaction documents.

M&A attorneys regularly draft side letters to handle carve-outs, special indemnities, employment arrangements, and other transaction-specific modifications that parties want to keep separate from the main purchase agreement.

Loan And Financing85% relevant

Side letters are commonly used in lending transactions to modify loan agreements, provide specific accommodations to borrowers, or document special terms for particular lenders in syndicated facilities.

Finance attorneys frequently need to draft side letters for covenant modifications, fee arrangements, and lender-specific terms without formally amending the underlying credit agreement.

Corporate Finance82% relevant

Side letters are essential in corporate finance transactions to document investor-specific rights, fee arrangements, or modifications to subscription agreements and investment terms.

Corporate finance lawyers regularly use side letters to address unique investor requirements, special pricing terms, or additional covenants in debt and equity financing transactions.

Side letters are used in securities offerings to provide specific investors with additional rights, disclosure, or terms that differ from the standard offering documents.

Securities lawyers often draft side letters to accommodate institutional investors' specific requirements regarding registration rights, information access, or governance matters in private placements and public offerings.

Asset Purchase75% relevant

Side letters are utilized in asset purchase transactions to address specific asset exclusions, assumption of particular liabilities, or special arrangements between buyer and seller.

Asset purchase attorneys frequently need side letters to document side agreements on transition services, employee matters, or specific asset-related terms without cluttering the main asset purchase agreement.

Frequently asked questions

Q

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

A

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.

Q

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

A

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.

Q

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

A

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.

Q

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

A

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.

Q

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

A

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.