Why We Invested in Letterhead

Asif Khan

We’re thrilled to share that we’re leading a $5.3M seed round in Letterhead alongside Reign Venture Partners, BDMI, Florida Opportunity Fund, McClatchy, and others. 

While email marketing remains one of the highest ROI channels for businesses, creating high-quality content products is expensive and time-consuming.

Companies tackle this challenge with fragmented software stacks that still leave significant manual work on the table. While businesses continually search for new ways to engage meaningfully with their stakeholders and gain deeper insights into their audiences, the current tools available on the market create a vacuum for a comprehensive, intelligent solution to fill the gap. 

Powered by AI and machine learning, Letterhead offers companies a smarter way to distribute more meaningful and relevant content to their audiences at scale. Users can manage multiple newsletters with the workflow of one, build custom templates, comprehensively track important campaign KPIs, and automatically adjust their newsletter strategy based on marketing performance. The platform integrates with all the major email service providers and marketing software tools so businesses can augment their existing marketing infrastructure and seamlessly incorporate the Letterhead platform into their existing workflows. The platform automates the entire end-to-end newsletter strategy and allows businesses to scale content creation efficiently and cost-effectively.

Chris Sopher, the CEO and Co-Founder of Letterhead, comes from a background in the media/publishing industry and previously founded WhereBy.us, a community development platform curating local news and events. Several of his colleagues there are now full-time team members with Letterhead. They have a deep asymmetric understanding of email as a marketing channel and ROI lever from their experience scaling a media company built around newsletters. Our many conversations with the Letterhead team and their customers gave us conviction in their long-term vision to build a leading software platform for organizations to operate and manage their personal media brands.

Letterhead will use the fresh infusion of capital to continue building out the platform and making key hires across product, engineering, and sales. Read more about open roles on Letterhead's website or on our portfolio companies jobs page

We’re thrilled to partner with the Letterhead team and look forward to supporting them in their mission to streamline newsletter creation, distribution, and monetization.

For informational purposes only. Not an offer to sell securities. Past investments shown are not indicative of future performance. LOVC Management, LLC (d.b.a Las Olas Venture Capital) is an SEC-registered investment adviser; registration does not imply a certain level of skill. See Form ADV for additional information.


Certain information contained herein has been obtained from third-party sources believed to be reliable as of the date listed; however, we cannot guarantee its accuracy or completeness. Other content reflects the views and opinions of LOVC as of the date presented and is subject to change without notice

We partner with exceptional founding teams building AI and software platforms that modernize outdated business workflows, with the goal of delivering measurable ROI, efficiency, and productivity gains.


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