Letterhead

Overview

Letterhead is a newsletter operating system designed for multi-title publishers, media organizations, agencies, and brands that manage multiple newsletters at scale. Founded by Christopher Sopher and Rebekah Monson over a decade ago in the local media business, the company recently raised $34 million in Series A funding led by Peakspan Capital in October 2025, signaling strong investor confidence in the platform's approach to newsletter management. The platform serves hundreds of publishers and agencies who collectively run thousands of newsletters, with notable clients including Patch local news network and various community publishers.

What differentiates Letterhead from traditional email marketing platforms is its positioning as middleware that sits on top of existing email service providers, CRMs, and content management systems rather than replacing them. The platform unifies newsletter portfolio management across multiple brands, audiences, and teams into a single workspace with automated editorial workflows, unified analytics, and built-in monetization tools. While most email platforms were built for marketing blasts or transactional emails, Letterhead treats newsletters as content products that need systematic operations, particularly for organizations running dozens or hundreds of publications simultaneously. For newsletter creators managing multiple publications or teams coordinating complex newsletter portfolios, Letterhead provides centralized control, automation, and revenue optimization that would otherwise require significant manual coordination and custom development.

Best For

Letterhead is ideal for multi-brand organizations, media companies, local news publishers, marketing agencies, and large content operations that manage multiple newsletters across different audiences or markets. The platform works particularly well for teams that feel overwhelmed by the operational complexity of running many newsletters, where coordination between editorial staff, ad sales, and production becomes difficult to manage through spreadsheets and manual processes. Newsletter creators who are actively monetizing through advertising, sponsorships, or internal promotions will benefit from Letterhead's ad management and self-service sales features. The platform suits organizations that already have established email infrastructure and subscriber bases but need better workflow management, unified analytics across their portfolio, and automated revenue operations.

Key Features

• Multi-Newsletter Portfolio Management: Letterhead provides a centralized dashboard where teams can manage 10, 100, or 1,000 newsletters with the same clarity and control as managing a single publication. This unified view allows organizations to oversee design, templates, and performance across their entire newsletter portfolio from one location, eliminating the need to log into multiple platforms or coordinate through scattered spreadsheets.

• Automated Content Curation and Assembly: The platform automatically ingests content from your CMS, RSS feeds, social media, podcasts, web links, and other sources, then assembles newsletters based on predefined templates and rules. This automation reduces the labor involved in gathering and selecting content for each edition, allowing teams to produce consistent newsletters without manually copying and pasting articles or rebuilding layouts from scratch each time.

• Built-In Ad Management and Monetization: Letterhead simplifies the entire advertising workflow from inventory management to fulfillment, providing tools to sell, place, track, and report on sponsorships, advertisements, and internal promotions across multiple newsletters. The platform includes an ad marketplace with automated cost-per-send and cost-per-click offers, self-service storefronts where advertisers can book and check out independently, and conditional content blocks that control what paying versus non-paying subscribers see.

• Self-Service Advertising Portal: The platform enables smaller-scale advertisers to book job listings, real estate listings, and other lower-cost ad units through an automated workflow where they visit your website, select their placement, pay, and set everything up themselves. This self-service capability makes smaller ad sales profitable by eliminating the manual coordination that typically erodes margins on low-value transactions.

• Unified Analytics Across Publications: Letterhead provides consolidated performance reporting across your entire newsletter portfolio, showing opens, clicks, unsubscribes, audience growth, engagement trends, and revenue attribution in a single interface. This unified view allows organizations to benchmark and compare performance across titles, identify best practices, and make data-driven decisions about resource allocation and content strategy.

• Template Standardization and Reusability: The platform allows you to create standardized design templates and reusable content blocks that can be deployed across multiple newsletters, ensuring brand consistency while reducing production time. Teams can auto-ingest articles, reuse design elements, and apply templates systematically, making it easy to maintain quality standards across dozens of publications without redesigning each issue individually.

• Automated Publishing Workflows: Letterhead standardizes editorial workflows with automation that handles scheduling, content population, review cycles, and publishing tasks across teams and titles. These automated workflows reduce manual coordination, eliminate missed deadlines, and free up editorial staff to focus on content quality rather than production logistics.

• Integration with Existing Infrastructure: Unlike platforms that require full migration, Letterhead integrates with your existing email service providers, CRM systems, and content management systems, pulling data from your systems of record while adding workflow coordination and intelligence on top. This middleware approach means you can adopt Letterhead without abandoning investments in platforms like Mailchimp, Constant Contact, or custom ESP solutions.

• Chrome Extension for Content Curation: The platform includes a browser extension that allows editorial teams to save articles directly into Letterhead's curation library as they browse the web. This frictionless content collection makes it easy for team members to contribute relevant articles throughout the week without disrupting their workflow or requiring them to remember URLs until newsletter assembly time.

• Dedicated Support and Media Expertise: Letterhead provides 24/7 human support and dedicated account management with team members who understand the media business and can help develop winning newsletter strategies. Users consistently praise the responsive support team and their willingness to build custom integrations and features for specific use cases, contrasting favorably with platforms where reaching a real person proves difficult.

Pricing

Letterhead does not publicly disclose its pricing structure, operating instead on custom pricing models tailored to each organization's needs, newsletter volume, and specific requirements. The platform positions itself as offering competitive value compared to the internal costs of managing complex newsletter operations manually, with users on review sites noting appreciation for the price relative to the functionality provided. Organizations interested in Letterhead need to contact the sales team directly for a custom quote based on factors like the number of newsletters managed, subscriber volume across their portfolio, monetization requirements, and integration needs. The Institute for Nonprofit News has secured exclusive pricing for INN members with discounts up to 20 percent, suggesting the company offers preferential rates for nonprofit news organizations and similar mission-driven publishers. Given the platform's focus on multi-title publishers and enterprise-level features, Letterhead appears positioned for organizations with established newsletter businesses generating revenue rather than individual creators or small operations just starting out.