Many organizations are currently investing in email newsletters, ranging from large international corporations to nonprofit organizations and local news outlets.

For some, email has become a primary focus, particularly after experiencing challenges with platforms like Facebook and Google over the past decade. However, the available tools often lack the necessary specificity or are geared towards marketing teams. What if you’re looking for a way to directly generate revenue from your newsletter’s content?

Letterhead is entering a competitive market of email SaaS products with a unique proposition: to comprehensively address the revenue and collaborative requirements of newsletter creators across diverse sectors. It consolidates ad sales, paid subscriptions, and newsletter content management into a single, efficient platform.

The company’s perspective on the future of newsletters—and its early customer base—differ significantly from typical Silicon Valley SaaS startups. This is because Letterhead originated as a spinout from WhereBy.Us, a Miami-based community publisher founded in 2014 with the launch of the local media site, The New Tropic. The publication achieved notable success in online local news by concentrating on the email newsletter format.

“Our initial aim was to develop a local media product that would inform people about the city, encourage participation, and cater to a new generation of local news consumers,” explains co-founder and CEO Chris Sopher in a video interview. “We considered various approaches, including opening a bar and hosting events, but ultimately focused on what was proving effective, and email was at the forefront.”

Demand for advertising space within these emails was strong, prompting the company to create a self-service payment system for advertisers. This allowed newsletter publishers to easily integrate and display the correct advertisements.

Building on this model and technology, the company launched or acquired newsletters in cities like Seattle, Portland, Orlando, and Pittsburgh, continually refining the tool throughout the process.

This development also revealed a wider market need.

“We frequently received inquiries from people impressed with our newsletter, asking what tools we utilized, as producing emails with the available options was often cumbersome,” Sopher clarifies.

(In this author’s experience, these tools typically involve a combination of Mailchimp, Constant Contact, or Sailthru, alongside a primary web publishing CMS such as WordPress, separate subscription software like Piano, and a separate system for managing advertisements.)

“We would explain that we used our own internally developed tools, and they would ask if they could use them as well. Initially, we declined. However, after repeatedly saying ‘no,’ we realized we should explore how to make those tools available to others, and that’s how Letterhead came to be.”

Currently, WhereBy.Us stands as one of the few success stories in a challenging decade for local news. Sopher states that their five city newsletters are consistently profitable through advertising—having recovered from a temporary decline earlier this year—and continue to expand.

The primary focus now is on Letterhead’s suite of tools, including the advertising system, a new paid subscription feature enabling options like paywalled email sections, user-friendly text editing and template formatting, and forthcoming analytics capabilities.

“We received the most feedback regarding sponsorships and advertisements, so that’s where we began,” explains co-founder and COO Rebekah Monson via email. “Our broader vision is to create a unified set of tools and services that support each other, fostering growth across all revenue streams and potentially extending beyond email. We’re observing demand from not only traditional media publishers but also marketers, nonprofits, universities, professional associations—organizations with engaged communities seeking to strengthen those relationships and generate revenue through that engagement.”

Within the landscape of email newsletter products, Letterhead’s emphasis on revenue generation and team collaboration positions it alongside Substack’s focus on individual writers and other platforms like Lede, which are designed for subscription-based news organizations.

Letterhead is specifically a hosted software solution that organizations pay to use, unlike open-source projects like Ghost. Similar to how Shopify provides a comprehensive suite of e-commerce features for online businesses, Letterhead aims to be the underlying engine powering your newsletter.

Considering the broader spectrum of email solutions in the SaaS market, Letterhead believes its market understanding and product design will outperform the highly competitive landscape of SaaS email products.

Since its soft launch earlier this year, Sopher reports a growing number of diverse customers are signing up. These include startups (Shoot My Travel), nonprofits (Vida y Salud and Refresh) and political groups (OD Action), in addition to local news publishers (VTDigger, Choose954 and Santa Cruz Local). Letterhead is also a partner in WordPress’ News Pack program, a collection of plugins for publishers using that CMS.

“We will always maintain a connection to media publishing… but there is a broader need beyond that industry,” he explains. “We’re also witnessing a trend where numerous organizations are engaging in [publishing]. Whatever the topic, there are professional journalists producing excellent work. However, it’s also likely that brands, agencies, nonprofits, or other organizations are creating valuable content and building communities around it—organizations that wouldn’t necessarily identify as part of the news industry.”

Sopher also highlights that the product is designed to be modular, allowing companies to utilize specific components and integrate its features with existing email service providers and technology stacks.

“We’re finding that smaller customers are attracted to the simplicity of having everything in one place without compromising monetization, while larger customers are integrating us as part of a more complex system as they expand their business or outgrow tools designed for individual creators,” he adds.

With revenue options established, Sopher says analytics and additional ESP integrations are the next priorities.

Throughout its history, WhereBy.Us has secured $5 million in funding from various sources in the tech and media sectors. Investors include the Knight Foundation, Jason Calacanis’ LAUNCH fund, Band of Angels, McClatchy, numerous smaller investors through Republic and SeedInvest, and most recently, a round led by Brick Capital.