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Automating The Wrong Things In Your Newsletter
Most think automation means scheduled sends. Here's what actually moves the needle.
Nate Kennedy
November 13, 2025
TL;DR: The top newsletters don’t start with fancy triggers, they start with onboarding. A strong welcome sequence, smart behavioral tagging, and referral follow-ups drive higher engagement, faster growth, and deeper connection. Automation done right improves the subscriber experience.
Last week, I analyzed 25 top-performing newsletter channels, and one video stood out: "The Automations Every Newsletter Publisher Needs." But here's what they didn't tell you...
While everyone was obsessing over scheduled sends and drip campaigns, the real winners were quietly building a completely different type of automation system. One that doesn't just save time, but it actually grows their audience faster.
I spent the last month reverse-engineering the automation strategies of newsletters pulling in 6-figure revenues. What I found will probably surprise you.
The Automation Hierarchy (Start Here, Not There)
Here's where 90% of newsletter publishers go wrong: they start with the sexiest automations, not the most profitable ones.
You know the drill. Day one, you set up your email scheduler. Day two, you build a basic welcome email. Day three, you're already dreaming about complex behavioral triggers and AI-powered personalization.
But successful publishers flip this script entirely.
ConvertKit's data shows that newsletters with proper onboarding automations see 40% higher open rates in month two.
Yet most creators spend weeks perfecting their sending schedule while their welcome sequence is a single "thanks for subscribing" email.
The hierarchy that actually works? Onboarding first, segmentation second, sending automation last.
Think about it: what good is a perfectly timed newsletter if new subscribers don't understand what they signed up for?
What's the point of consistent sending if you're sending the same content to your crypto enthusiasts and your productivity nerds?
The 3 Non-Negotiable Automations
After analyzing successful newsletters like Morning Brew, The Hustle, and dozens of smaller publishers, three automations appear in every high-performing setup:
1. The Value-First Welcome Sequence
Forget the boring "Welcome to my newsletter!" approach. Top publishers use their welcome sequence to immediately deliver their best content while setting clear expectations.
Austin Rief from Morning Brew welcome sequence teaches them how to read financial news more effectively. Five emails, each packed with actionable insights. Result? 73% of new subscribers are still opening emails 30 days later.
2. Behavioral Trigger System
This isn't about complex AI. It's about simple "if this, then that" logic that makes your readers feel seen.
When someone clicks three links about productivity but zero about investing, tag them. When someone opens every email for two weeks straight, they get your premium content preview.
When someone hasn't opened in 30 days, they get your "we miss you" sequence.
ConvertKit founder Nathan Barry increased his newsletter's lifetime value by 200% using just five behavioral triggers.
3. Referral Follow-Up Engine
Here's the automation most publishers completely ignore: following up on referrals with both the referrer and the new subscriber.
When someone refers a friend, most newsletters send a generic "thanks!" email. Smart publishers send a personalized note, highlight the referrer in their next issue, and automatically enroll the new subscriber in a special "referred by [name]" sequence.
ReferralCandy data shows this approach can 3x your referral program results.
The Personal Touch Paradox
"But won't automation make my newsletter feel robotic?"
This is the objection I hear most, and it reveals a fundamental misunderstanding of what automation should do.
The best automation doesn't replace personal connection—it creates more opportunities for it.
Take James Clear's newsletter. His automation system identifies highly engaged readers and flags them for personal outreach. He's personally replied to thousands of readers, but only because his automation system told him who to prioritize.
Similarly, Tim Ferriss uses automation to segment his audience so precisely that each group gets content that feels personally curated.
His tech subscribers get different links than his investing subscribers, even though it's the same newsletter.
The key? Automation should make your content more relevant, not more generic.
Your 30-Day Automation Blueprint
Week 1: Build your welcome sequence. Three emails minimum: value delivery, expectation setting, and community invitation.
Week 2: Set up basic segmentation. Use signup forms, surveys, or click behavior to create 3-5 audience segments.
Week 3: Create your engagement triggers. Flag super-fans, re-engage inactive subscribers, and reward referrers.
Week 4: Test and optimize. Look at your metrics, survey your audience, and refine your automations based on real feedback.
Start simple. A basic welcome sequence that delivers value beats a complex automation system that confuses your audience.
Most importantly, remember that automation is a multiplier. If your content isn't great, automation won't save you. But if your content resonates, the right automations can turn a good newsletter into an unstoppable growth engine.
Ready to build your first newsletter automation?
Start with your welcome sequence this week. Your future subscribers (and your bank account) will thank you.
Press Send!
~ Nate Kennedy
