Letterhead

This week, we shipped *Sync from Docs.* 📄 ➡️ 💌 Editorial teams write newsletters in Google Docs. Letterhead sends them. One click. Zero rebuilding. There's a part of newsletter production that doesn't show up on any org chart — the hour your team has been quietly losing every send, when somebody opens the email tool and rebuilds the editor's draft from scratch. We've been calling it the last mile. Today, we ended it. Sync from Docs is the first of several integrations we're building so Letterhead meets editorial where they already live — Docs, Notion, your CMS, Slack — instead of asking them to come live in our app. Editors deserve their hour back. https://lnkd.in/egEj7R-r

On stage at eMerge Americas today, our very own Chris 🫶 Adamo is MC’ing the AI & Deep Tech stage, helping lead the conversation on what’s next in AI. If you see him, be sure to stop by and say hi!

Last week Letterhead brought our free mini book fair to #ONA26 and we're still buzzing from the conversations. Nearly 300 people stopped by to grab a book or hat and talk about what they're building. So many teams are tapping into AI in smart ways right now and it was incredible hearing how people are thinking about their newsletter operations. This is why we do what we do. Thanks to everyone who came by. More to come.

Chicago delivered. 🎉 The Letterhead team just wrapped an incredible week at the Online News Association conference, and we’re still buzzing. From our bookstore activation that brought the Letterhead community together IRL, to a cold (but unforgettable) Cubs night game at Wrigley Field with Marfeel and PressReader , to belting our hearts out at a piano bar — this week was a reminder of why we love this industry and the people in it. We had the chance to reconnect with so many brilliant minds in local and digital news: Ashley Lewis (Shaffer) • Ben Beachler • Bruce Pinchbeck • Chris 🫶 Adamo • Christopher Sopher • Cynthia DuBose • Dion Rabouin • Evan Morse • Gregory Silberman • Idalmy Carrera-Colucci • Kimberly Cregan • Lindsey Dunahoo Kristyn Wellesley, M.A., AIGP Matthew Bain Matthew DeFour Michelle Lopez Ross Maghielse Sarah Patterson Sofia Alvarez Summer Moore Synne Nikolaisen Tracy Brown Tracy Maher Tracy Ziemer Tyson Bird Ursula Murua Kateline Hullar Monica Guzman Rubina Fillion Ryan Struyk Barbara Chai Gabriela Fernandez Drew Dickson-Parham …and so many more. If we crossed paths this week, thank you for the conversation, the laughs, and the inspiration. The future of news is being built by people like you. We’re proud to be part of it. 🗞️ #ONA26 Ashley Lewis (Shaffer) #Letterhead #NewsInnovation #media #OnlineNewsAssociation

We're back at it. The Letterhead Book Fair is live at ONA26 in Chicago and NewsMega in Austin — today and tomorrow. The deal is simple: stop by our booth, grab a free book, and check out what people in this industry are actually reading and recommending to each other. This round, we partnered with Pantheon Books (Penguin Random House) to get some of their latest releases on the table, and we are very grateful for their support. It's been a blast so far. Come say hi. (Book links in the comments.)

We're bringing a mini book fair to a couple of conferences this month, and we need your help stocking the shelves. 📚 What's a book you love that you'd hand to a friend or colleague? Any genre. Tell us what you picked and a little about why. tryletterhead.com/bookfair

Just posted the replay of our latest YES, Reply session with Jacqué Palmer. We talked about newsletter strategy for 2026 through a simple lens: treat newsletters like products, not output. Key ideas we covered: Audience: who is this actually for? Value: what promise does it deliver? Revenue: how does it connect to the business? Growth: how do you acquire + manage churn intentionally? Operations: how does it get made (and scale)? We also got into inbox fatigue + where AI helps (and where it doesn’t). ▶️ Watch the replay: Link in comments Question for operators: what’s your biggest constraint right now—resourcing, workflow, quality, or growth? #Newsletters #EmailMarketing #AudienceGrowth #ProductManagement #AI

Looking forward to this conversation with Jacqué Palmer and Bruce Pinchbeck on the current state of newsletters. Join us on Wednesday! Link in comments

Most organizations are still running newsletters like marketing campaigns—one-off sends, disconnected tools, no portfolio-level thinking. But newsletters aren't campaigns. They ship continuously, involve multiple teams, and compound engagement over time. On Feb 19, we're hosting a 60-minute session on what it actually looks like to run newsletters as products in 2026. We'll cover: → A simple framework for product-minded newsletter operations → A realistic view of AI in newsletters—what helps, what hurts trust → Practical tactics for engagement in an overstimulated inbox Hosted by Bruce Pinchbeck (Co-founder, Head of Brand) and Jacqué Palmer (Product Manager, formerly Senior Editorial Director for Newsletters at The Boston Globe). No fluff. Operational thinking for teams scaling newsletters. Quick update — we moved Episode 01 to February 25 (Jacqué's family got hit with a bug, she'll be back at full strength). Same show, same everything. If you haven't registered yet... LINK IN COMMENTS

Most newsletter programs don’t stall on content, but on clarity. The fastest path from “we have readers” to “we have revenue” is a clean chain, and it all starts with a persona. Define the persona, align the message, package the offer, pitch the right sponsors, and monetize with discipline. What if there’s a weak link? The whole system drags. Follow the five stages and identify clear signals at each step. If you can’t spot the signal, you don’t advance.