Letterhead Raises $34M to Scale the Newsletter Operating System

Series A led by Peakspan Capital accelerates growth of the platform already powering thousands of newsletters across leading brands and publishers.

MIAMI, FL, UNITED STATES, October 22, 2025 /EINPresswire.com/ -- Letterhead, the company behind the Newsletter Operating System, today announced it has raised $34 million in Series A funding led by Peakspan Capital. The investment will accelerate product development, team expansion, and market growth as more organizations adopt Letterhead to manage and scale their newsletter programs.

Newsletters have surged in importance as brands seek reliable, owned channels in an environment shaped by privacy regulation, declining ad efficiency, and fractured content ecosystems. And yet, managing many newsletters across audiences, brands, and markets has remained complex and costly. Letterhead solves this challenge by unifying newsletter management, automating production, and surfacing deep audience insights, all on top of a company’s existing ESPs and CRM systems.

Letterhead solves this challenge with purpose-built infrastructure for how newsletters actually run. The platform unifies newsletter management, automates production, and connects audience, content, and performance data, all on top of a company’s existing ESP, CRM, and CMS.

“Newsletters aren’t email. They’re content products,” said Christopher Sopher, co-founder and CEO of Letterhead. “Our system helps organizations operate their newsletters as products: scalable, measurable, and continuously improving. With Letterhead, teams can run 10, 100, or 1,000 newsletters with the same confidence and clarity as one.”

Leading brands and publishers rely on Letterhead to:

- Centralize operations: Manage entire newsletter portfolios across brands, audiences, and teams with a unified view of performance and ROI.
- Automate production: Streamline editorial workflows to assemble and deliver newsletters faster, with fewer errors.
- Grow intelligently: Surface data-driven recommendations to improve engagement, monetization, and long-term audience value.

“Letterhead’s platform is purpose-built for this moment,” said Matt Melymuka, Co-Founder and Managing Partner at Peakspan Capital, who will join Letterhead’s Board of Directors. “Many brands today possess a vast reservoir of valuable first-party data, yet have failed to fully leverage its potential. Letterhead’s platform empowers brands to unlock the power of this data seamlessly through a workflow-centric platform approach underpinned by automation and injected with AI. Chris, Rebekah, and the entire Letterhead team embody the entrepreneurial spirit we seek in our partners, having built an outstanding business in a high-growth market that has shown tremendous growth since inception with remarkable capital efficiency. We’re thrilled to be supporting the Letterhead team as they embark on this next phase of their journey.”


About Letterhead

Letterhead’s Newsletter Operating System helps organizations run high-performing newsletter programs at scale. By unifying management, automating production, and delivering actionable insights, Letterhead makes it simple for multi-brand organizations to run dozens or hundreds of newsletters with the same consistency and impact as one. Visit www.tryletterhead.com to learn more.

About Peakspan Capital

Peakspan Capital is a growth equity firm with over $2.5B in AUM, partnering with more than 55 high-growth software companies. Learn more at www.peakspancapital.com.

Bruce Pinchbeck
Letterhead
bruce@tryletterhead.com
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