We’ve raised $34m to power the Newsletter Operating System
Announcing our Series A funding, led by Peakspan Capital, to make newsletter operations effortless at scale and turn every send into smarter engagement and stronger revenue.
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Before founding Letterhead, Christopher co-founded WhereBy.Us, a platform that connects locals with the best of their cities. He also worked at the Knight Foundation, where he supported innovative ideas to make cities more vibrant and dynamic.
Today, we’re announcing $34 million in Series A funding, led by Peakspan Capital, to make newsletter operations effortless at scale and turn every send into smarter engagement and stronger revenue.. This isn’t just a milestone for us. It’s a signal of where the world is heading.
Every brand’s most critical lever
Email has quietly become the most dependable, direct relationship channel a brand owns. As ad performance declines and privacy regulations tighten, companies are realizing that newsletters are how they directly, consistently, and intentionally reach their audiences.
At first, that meant one newsletter. Then two. Then a dozen. Now, large media companies, publishers, agencies, and multi-brand organizations often manage hundreds of newsletters, each serving a different audience, market, or product line.
That kind of growth is a sign of success. But it’s also created a new kind of operational chaos.
The problem we see every day
Most organizations still run newsletters inside systems built for marketing blasts and transactional email, not for multi-brand content, editorial workflows, and ambitious growth goals. This forces editorial and audience and revenue teams into models that don’t fit. With content, data, promotions and advertising all living in disparate places, teams working on newsletters face risk of errors, manual workflows, and limited ROI visibility that makes optimization a guessing game.
Today’s tools don’t treat newsletters like the living content products they are. That’s where Letterhead comes in.
A new system for how newsletters actually run
Letterhead exists because we believe newsletters deserve their own purpose-built infrastructure, designed to sit on top of your ESP, CRM, and CMS. To be clear: we’re not another place to send email. We’re the platform that helps organizations operate newsletters as products, making them scalable, measurable, and continuously improving. This means giving teams a single workspace to oversee every newsletter, automated editorial workflows that eliminate manual work, and unified analytics and recommendations to grow both engagement and revenue.
With Letterhead, teams can run 10, 100, or 1,000 newsletters with the same confidence and clarity as one.
The Newsletter Operating System is no longer just an idea. It’s the infrastructure already powering thousands of newsletters across leading brands and publishers.
This next chapter for us is about scale: scaling our technology, our team, and our impact. We’re deepening integrations with the tools our customers already use, expanding automation and analytics that make complex programs simple to run, and extending the reliability and performance needed by global organizations.
To our customers and partners building stronger audience relationships through newsletters: thank you for believing in our team and our product, and helping us push this vision forward.
We’re just getting started.