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Letterhead

Letterhead

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

Last Round

Series A

Oct 22, 2025

Est. Valuation

$136M

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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Letterhead Comparables

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

Letterhead comparables — related companies by embedding similarity
CompanySimilarityMarket Cap
beehiiv
78%
OpenWeb
77%
Passendo
76%

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

Explore SEC and related filing metadata, where available.

Letterhead filings preview — column headings only; records require access
TypeDateAmount OfferedAmount SoldFilingPagesDownload

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Frequently Asked Questions

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

Is Letterhead a public or private company?

Letterhead is a private company.

What is the current stock price of Letterhead?

Letterhead is a private company with no public stock price. No recent secondary market data is available.

How much is Letterhead worth (valuation)?

Valuation information for Letterhead is not publicly available.

Can I buy Letterhead stock?

Letterhead shares may be available on secondary markets subject to transfer restrictions. Caplight facilitates secondary market transactions for accredited investors. Visit https://www.caplight.com to learn more.

When was Letterhead's last funding round?

Letterhead's most recent funding round was Series A on October 22, 2025.

Who are the main investors in Letterhead?

Key investors in Letterhead include Reign Ventures.

Will Letterhead IPO soon?

No public IPO plans have been announced for Letterhead.

How can I track Letterhead secondary market activity?

Caplight tracks bids, offers, and trades for private companies. Visit https://www.caplight.com to monitor Letterhead's secondary market activity and sign up for updates.

Firmographic Details

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

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