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October 22, 2025 - Deals

Letterhead Raises $34 Million In Series A Funding Led By Peakspan Capital

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Letterhead, the company building the “Newsletter Operating System,” has raised $34 million in Series A funding led by Peakspan Capital to help organizations manage and scale their newsletter operations. The platform streamlines workflows for brands, publishers, and agencies managing dozens or even hundreds of newsletters, providing tools for automation, analytics, and revenue optimization. With this new funding, Letterhead plans to expand its technology, deepen integrations with existing tools, and continue powering smarter, more efficient newsletter operations for leading media companies and brands. FOUNDERS: Bruce Pinchbeck, Christopher Sopher & Rebekah Monson INVESTOR: Peakspan Capital ROUND: Series A AMOUNT: $34,000,000 HQ: #Miami #Florida #VentureCapital #Letterhead #BrucePinchbeck #ChristopherSopher #PeakspanCapital #RebekahMonson #TradedVC