Letterhead

Series ARaised Since Featured

The newsletter operating system

AI-powered platform that helps teams plan, produce, and monetize multiple newsletters at scale.

Founded January 2020Miami, FL20-50 people$39.3M raisedFeatured at Pre-Seed

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About

Letterhead is the newsletter operating system that unifies management, automates production, and surfaces deep audience insights — all on top of a company's existing ESPs, CRMs, and CMS platforms. Born out of WhereBy.Us, a Miami-based community media company, Letterhead spun out as a standalone product after the team realized the newsletter tooling they built internally could serve a much larger market. The platform enables organizations to run 10, 100, or even 1,000 newsletters with the same confidence and clarity as one. Leveraging AI, Letterhead streamlines newsletter creation, distribution, and monetization for publishers, agencies, and marketing teams, helping them produce meaningful, targeted content products at scale. With thousands of newsletters powered across leading brands and publishers, Letterhead raised a $34M Series A led by PeakSpan Capital in October 2025.

DailyDropout Take

Letterhead caught our eye as a newsletter infrastructure play — not another Substack competitor, but a meta-layer that sits on top of existing email stacks. Founded by the WhereBy.Us team who lived the pain of running community newsletters in Miami, they built tooling that now powers 1,800+ newsletters. The $34M Series A from PeakSpan Capital validates that enterprise newsletter management is a massive, underserved market.

Discovery signal: Unique positioning as newsletter infrastructure (not a platform replacement), strong Miami ecosystem roots, rapid growth from seed to Series A with 6x funding increase

What Makes Them Unique

Unlike newsletter platforms that replace your email stack, Letterhead sits on top of existing ESPs and CRMs as infrastructure — enabling organizations to manage hundreds of newsletters with unified analytics, automated workflows, and monetization tools in a single operating system.

1,800+

Newsletters Powered

$39.3M

Total Raised

$34M

Series A

Target Markets

PublishersMedia CompaniesAgenciesMulti-Brand OrganizationsEnterprise Marketing Teams

Founders

Christopher Sopher

Co-Founder & CEO

Previously co-founded WhereBy.Us. Former Knight Foundation program officer. UNC Chapel Hill graduate.

Rebekah Monson

Co-Founder & COO

Previously co-founded WhereBy.Us and The New Tropic. MFA in Interactive Media from University of Miami. Journalism background from Louisiana State University.