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Legal Pro Rata Side Letter

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LEGAL PRO RATA SIDE LETTER

This Pro Rata Side Letter (the Agreement) is entered into as of Day: Month: Year: by and between Investor Name: (Investor) and Company Name: (Company).

RECITALS

WHEREAS, the Company is undertaking a proposed issuance of securities described as (Securities) in a financing to occur on or about Month: Day: Year: (Offering).

WHEREAS, the Investor is a current or prospective holder of certain securities of the Company and has requested, and the Company has agreed in certain circumstances, to grant the Investor a right to purchase additional securities on a pro rata basis to permit the Investor to maintain its proportionate ownership.

WHEREAS, the parties desire to set forth in this Agreement the terms and conditions under which the Company will provide pro rata participation rights to the Investor.

NOW, THEREFORE, in consideration of the mutual covenants and agreements contained herein and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties agree as follows:

1. DEFINITIONS

For purposes of this Agreement, the following terms shall have the meanings set forth below:

(a) "Pro Rata Percentage" means the percentage set forth below representing the Investor's right to participate in future issuances, calculated as the ratio of the Investor's fully diluted ownership immediately prior to such issuance. Pro Rata Percentage:

(b) "Proposed Issuance" means any issuance by the Company of equity securities, convertible securities, options, or other securities that would dilute existing equity holders, other than Exempt Issuances (as defined below).

(c) "Exempt Issuances" shall mean (i) issuances to employees, consultants or directors pursuant to a Company equity incentive plan approved by the Board, (ii) securities issued in a bona fide strategic transaction approved by the Board, and (iii) any issuance expressly excluded in a writing signed by the Investor.

2. GRANT OF PRO RATA RIGHT

Subject to the terms and conditions of this Agreement, the Company hereby grants to the Investor the right, but not the obligation, to purchase up to the Investor's Pro Rata Percentage of any Proposed Issuance on the same economic and other material terms offered to other purchasers in such Proposed Issuance (the Pro Rata Right).

3. EXERCISE PROCEDURES

(a) The Company shall provide the Investor written notice of any Proposed Issuance (the Notice) not less than calendar days prior to the expected closing date, specifying the number, price and general terms of the securities proposed to be issued and the date by which the Investor must elect to exercise its Pro Rata Right (the Exercise Deadline).

(b) To exercise the Pro Rata Right in whole or in part, the Investor must deliver to the Company prior to the Exercise Deadline a written notice of exercise setting forth the amount to be purchased and payment in accordance with the procedures set forth in the Notice.

(c) Failure by the Investor to timely deliver a notice of exercise and payment shall be deemed a waiver of the Investor's rights with respect to such Proposed Issuance, but shall not operate as a waiver of the Investor's rights with respect to subsequent Proposed Issuances.

4. LIMITATIONS, TRANSFER AND ASSIGNMENT

(a) The Pro Rata Right is personal to the Investor and shall not be assignable except with the prior written consent of the Company, which consent shall not be unreasonably withheld, except that the Investor may assign all or a portion of its rights under this Agreement to any affiliate or to any entity that acquires all or substantially all of the Investor's assets without the Company's consent.

(b) The Investor's right shall terminate upon the first to occur of (i) the closing of a Qualified Public Offering (as defined below), (ii) the dissolution of the Company, or (iii) a written agreement between the parties that terminates the right. For the purposes of this Agreement, "Qualified Public Offering" means an offering resulting in aggregate gross proceeds to the Company of at least .

5. REPRESENTATIONS AND WARRANTIES

(a) The Company represents and warrants to the Investor that: (i) it has the requisite corporate power and authority to enter into and perform this Agreement; (ii) this Agreement has been duly authorized, executed and delivered by the Company and constitutes a valid and binding obligation enforceable against the Company in accordance with its terms; and (iii) the Board of Directors has taken all necessary corporate action to approve the grant of the Pro Rata Right.

(b) The Investor represents and warrants to the Company that: (i) it has the power and authority to enter into and perform this Agreement; (ii) it is acquiring any securities pursuant to an exercise of the Pro Rata Right for investment purposes and not with a view to distribution; and (iii) the execution and performance of this Agreement does not violate any other agreement by which the Investor is bound.

6. CONFIDENTIALITY

The parties acknowledge that the terms of this Agreement and any non-public information disclosed pursuant to the exercise of the Pro Rata Right are confidential. Neither party shall disclose such information except to its employees, advisors or potential purchasers on a need-to-know basis, provided that such recipients are bound by confidentiality obligations no less restrictive than those in this Agreement or as otherwise required by law.

7. REMEDIES

The parties agree that monetary damages would be an inadequate remedy for any breach of this Agreement and that, in addition to any other remedies available at law or equity, the non-breaching party shall be entitled to injunctive relief to enforce the provisions of this Agreement without the necessity of posting bond.

8. NOTICES

All notices, requests, consents and other communications required or permitted hereunder shall be in writing and shall be delivered to the addresses set forth below or to such other address as a party may designate by notice to the other in accordance with this Section. Notices shall be deemed given when delivered personally, sent by nationally recognized overnight courier, or three business days after deposit in the mail, postage prepaid, certified or registered mail, return receipt requested.

9. GOVERNING LAW

This Agreement shall be governed by and construed in accordance with the laws of the State of without regard to principles of conflicts of laws.

10. ENTIRE AGREEMENT

This Agreement, together with any documents referenced herein, constitutes the entire agreement between the parties with respect to the subject matter hereof and supersedes all prior and contemporaneous agreements, understandings and negotiations, whether written or oral, between the parties regarding such subject matter.

11. SEVERABILITY

If any provision of this Agreement is held to be invalid, illegal or unenforceable in any respect, such provision shall be severed and the remainder of this Agreement shall remain in full force and effect to the maximum extent permitted by law.

12. AMENDMENT; WAIVER

No amendment, modification or waiver of any provision of this Agreement shall be effective unless in writing and signed by the parties hereto. No failure or delay by any party in exercising any right shall operate as a waiver of that right.

13. COUNTERPARTS

This Agreement may be executed in counterparts, each of which shall be deemed an original and all of which together shall constitute one and the same instrument. Signatures transmitted by electronic means shall be deemed original signatures for all purposes.

14. MISCELLANEOUS

The obligations and rights of the parties under this Agreement shall inure to the benefit of and be binding upon the parties and their respective permitted successors and assigns. The headings in this Agreement are for convenience only and shall not affect interpretation.

Investor

Party Label:

By:

Date:

Company

Party Label:

By:

Date:

Enter text✕

What the Legal Pro Rata Side Letter Is and When It Applies

A Legal Pro Rata Side Letter is a limited-purpose agreement between an investor and an issuer that grants the investor the contractual right to participate pro rata in future financing rounds. It typically sits alongside a subscription agreement, purchase agreement, or investor rights agreement and clarifies allocation mechanics, time windows for exercise, and transfer restrictions. Side letters are negotiated documents that allocate incremental rights without changing the primary deal economics; they are commonly used in venture financings, private placements, and follow-on funding to preserve ownership percentage on dilution events.

Why a Pro Rata Side Letter Matters to Investors and Issuers

A clear pro rata side letter protects an investor’s ability to maintain ownership percentage and prevents ambiguity at later rounds. For issuers, it documents expectations and timelines for follow-on allocations, reducing disputes and facilitating orderly cap table management.

Why a Pro Rata Side Letter Matters to Investors and Issuers

Typical Parties Who Use This Side Letter

Common users include institutional and high-net-worth investors, founders, and corporate counsel who need a documented allocation mechanism.

  • Lead investors protecting follow-on allocation rights and anti-dilution expectations.
  • Startup founders and general counsels documenting investor commitments and operational timing.
  • Fund managers and syndicates coordinating exercise windows and capital calls across LPs.

The document also assists board members and subsequent investors by recording pre-agreed participation mechanics and notice procedures.

Essential Elements Found in a Professional Pro Rata Side Letter

A robust side letter defines scope, mechanics, notice procedures, timing, conditions precedent, and remedies to make follow-on participation operational and enforceable.

Grant

Explicit pro rata participation grant describing percentage or formula used to calculate allocation in future financings.

Exercise Window

Fixed notice and election periods, including how long the investor has to accept an allocation and deliver capital.

Allocation Mechanics

Method for calculating shares or units offered, treatment of convertible instruments, and rounding rules where applicable.

Conditions

Conditions precedent to participation, such as issuer compliance, minimum round size, or investor standing requirements.

Transfer Rules

Restrictions on assignment, permitted transfers to affiliates, and any consent mechanics for novation or delegation.

Remedies

Remedies for breach including injunctive relief, specific performance, or agreed damages tied to dilution events.

Step-by-Step: Completing and Executing the Side Letter

Follow these practical steps to prepare a valid and usable pro rata side letter.

  • 01
    Draft Agreement: Populate parties, percentage, mechanics, and timelines.
  • 02
    Internal Review: Have counsel confirm consistency with the main transaction documents.
  • 03
    Signatures: Obtain authorized signatures and dates from all parties.
  • 04
    Recordkeeping: Store executed copy with cap table and investor records.

Digital Workflow Settings for Online Completion

Configure your eSignature workflow to match legal and operational requirements before sending.

Field Configuration
Signer Order Sequential or parallel routing depending on signatures needed
Authentication Email + SMS code or advanced KBA for high assurance
Attachments Attach cap table snapshot and subscription agreement
Retention Enable download of signed PDF and audit trail

Where to Send or File the Executed Side Letter

A side letter is typically circulated to defined countersigners and stored by the issuer and lead investor for administrative use.

  • Issuer Counsel: Receive fully executed copy for corporate records
  • Investor Records: Investor keeps original and audit trail
  • Cap Table Admin: Update ownership and allocation records
  • Registrar / Transfer Agent: Provide if required for share issuance

Digital Signing and File Format Considerations

Choose a platform that supports PDF/DOCX, audit trails, and optional advanced authentication for high-assurance executions.

  • Accepted Formats: PDF, DOCX
  • Authentication: Email, SMS, KBA
  • Integrations: CRM and storage connectors

Common Deadlines and Timing Clauses to Define

Explicit timing clauses prevent missed opportunities and disputes; define each deadline in the letter using calendar dates or fixed days.

Election Period:

Number of days after notice during which investor must elect to participate.

Funding Window:

Days allowed for delivering funds after election acceptance.

Notice Lead Time:

Issuer’s advance notice period to investors before a qualifying round.

Waiver Period:

Time within which the investor may waive rights in writing.

Record Update:

Deadline for issuer to update cap table following closing.

Key Milestones in a Pro Rata Side Letter Lifecycle

Sequence these milestones to align operational steps with contractual deadlines and investor expectations.

01

Negotiation

Agree terms and percentage before closing.

02

Execution

Obtain signatures and finalize dates.

03

Notice and Election

Issuer issues notice; investor elects within window.

04

Funding and Issuance

Investor funds and issuer issues securities.

Common Preparation Mistakes to Avoid

  • Failing to define calculation method for allocations, causing rounding and entitlement disputes.
  • Using inconsistent party names between the side letter and primary transaction documents.
  • Omitting conditions precedent such as minimum round size or issuer compliance requirements.
  • Neglecting to update the cap table and transfer agent records after exercise.

Legal and Commercial Risks from an Incorrect Side Letter

Loss of Rights: Investor may forfeit participation rights.
Breach Claims: Counterparties can seek damages or specific performance.
Tax Consequences: Incorrect reporting may trigger backup withholding.
Cap Table Errors: Improper issuance causes ownership disputes.
Enforceability Issues: Ambiguities can defeat enforcement in court.
Regulatory Risk: Securities law violations or disclosures may result.

Security, Compliance, and Platform Certifications to Check

In Transit: TLS 1.2/1.3 encryption
At Rest: AES-256 encryption
Standards: SOC 2 Type II available
Healthcare: HIPAA compliant (BAA required)
FDA/Clinical: 21 CFR Part 11 support available
Authentication: Multi-factor signer options

How a Pro Rata Side Letter Differs from Similar Documents

Compare common contractual alternatives to confirm that a side letter is the appropriate tool for allocation rights.

Criteria Pro Rata Side Letter ROFR Agreement Investor Consent
Purpose allocation right preemption on transfers single-round approval
Transfer Effect shares issued later blocks third-party transfers changes governance only
Typical Term multi-round usually perpetual one-off or limited
Enforceability contractual contractual contractual

Typical eSignature Vendor Comparison for Executing Side Letters

Basic commercial differences among eSignature providers can affect cost, compliance, and bulk execution capability when managing many investor side letters.

signNow DocuSign Adobe Sign PandaDoc HelloSign
Starting Price $8/user/mo $15/user/mo $14/user/mo $19/user/mo $15/user/mo
Free Trial 7-day free trial Varies Varies Varies Varies
Bulk Send Yes (Premium) Yes Yes Yes No
Audit Trail Yes Yes Yes Yes Yes
HIPAA Compliant Yes Yes Yes No No
Envelope Cap No cap 100 envelopes/user/year Varies Varies Varies

Practical Use Cases for a Pro Rata Side Letter

Real-world scenarios show how side letters prevent dilution and streamline follow-on participation.

Early-Stage Financing

A lead investor secures a 10% pro rata right to future rounds to maintain ownership

  • This ensures priority in follow-on allocations
  • The side letter clarifies timing, payment mechanics, and reporting obligations so the issuer can automate cap table updates without dispute.

Follow-On Allocation

An existing investor negotiates a formula-based right tied to holdings at closing

  • The formula addresses convertible instruments and rounding
  • Clear mechanics reduce later negotiation, enabling quick capital calls and immediate issuance on funding.

Frequently Asked Questions About the Legal Pro Rata Side Letter

Answers to common legal, procedural, and execution questions about pro rata side letters and electronic execution.


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