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Letterhead

Letterhead

Private
Miami, FloridaEnterprise Softwarehttps://www.tryletterhead.com/

Last Round

Series A

Oct 22, 2025

Total Funding Raised

$39.3M

Momentum

Top 50%

of companies Caplight tracks

Company Overview

Letterhead is a business/productivity software company that provides a platform to help teams plan, produce, and monetize newsletters.

Sector

Enterprise Software

Verticals

Digital Publishing, Marketing, Digital Advertising, Workflow Automation, News & Media

Business Model

B2B

Customer Profile

Subscription SaaS

AI Layer

Application

Keywords

newsletter managementnewsletter operating systemSaaSnewsletter platformemail newsletter softwarenewsletter monetizationB2B SaaSeditorial workflowad inventory managementcontent curationaudience engagementemail marketing automationnewsletter tech stackcreator economy tools

Historical Pricing

Historical view of private secondary pricing and transaction trends.

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Caplight Momentum Score

Proprietary index based on bid/ask volume and sentiment.

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Track how buyer interest and sentiment changes over time.

Letterhead Comparables

Compare Letterhead with similar companies based on industry and business-model similarity.

Letterhead comparables — related companies by embedding similarity
CompanySimilarityMarket Cap
Passendo
77%
beehiiv
76%
OpenWeb
71%

Letterhead Funding Rounds

Historical fundraising activity

Data table
RoundDateAmount RaisedValuationInvestorsSources
Series AOct 22, 2025
SeedNov 29, 2023

Key People

Founding team and executive leadership

Rebekah Monson

Cofounder and COO

Founding Team

Christopher Sopher

Cofounder & CEO

Founding Team

Letterhead Investors

Notable investors and investment history

Letterhead investors
InvestorRounds
Reign VenturesSeed
Las Olas Venture CapitalSeed
Florida Venture ForumSeed
PeakSpan CapitalSeries A
McClatchySeed
BDMISeed

Market signals

Structured signals derived from secondary market and firmographic data.

  • Oct 22, 2025

    $34M round led by PeakSpan Capital.

  • Sep 27, 2025

    Added TechStars, a venture capital/startup accelerator, as a customer.

Letterhead Filings

SEC and related filings with document metadata.

Data table
TypedDateAmount OfferedAmount SoldFillingPagesDownload
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Letterhead Filings

SEC and related filings with document metadata.

Frequently Asked Questions

Common questions about Letterhead's valuation, stock price, and market status.

Firmographic Details

HeadquartersMiami, Florida
Employee Range30
Year Founded2020
Last FundingOct 22, 2025

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