AI & Automation
Personas
SaaS & Startup
Time to ROI
Short-term (< 3 months)
Last year, I was working on a complete website revamp for a Shopify e-commerce client. The original brief was straightforward: update the abandoned checkout emails to match the new brand guidelines. New colors, new fonts, done.
But as I opened the old template—with its product grid, discount codes, and "COMPLETE YOUR ORDER NOW" buttons—something felt off. This was exactly what every other e-commerce store was sending.
That's when I realized something crucial: in a world of automated, templated communications, the most powerful differentiation might just be sounding like an actual person who cares about solving problems—not just completing transactions.
Here's what you'll learn from my experience completely reimagining onboarding drip campaigns:
Why the "newsletter-style" approach converts better than traditional templates
How addressing real friction points beats generic marketing copy
The psychology behind first-person messaging in automated emails
How to turn abandoned checkout emails into customer service touchpoints
Why adding friction (troubleshooting guides) actually increases conversions
This isn't about A/B testing subject lines or optimizing send times. This is about fundamentally rethinking what onboarding emails should accomplish. Most e-commerce businesses are missing the biggest opportunity: turning automated sequences into genuine relationship builders.
Industry Reality
What every marketer has already tried
Walk into any marketing conference or scroll through any SaaS blog, and you'll hear the same onboarding email advice repeated like gospel:
"Keep it simple" - Strip down to essential elements, remove distractions
"Optimize for mobile" - Big buttons, minimal text, finger-friendly design
"Create urgency" - Time-sensitive offers, countdown timers, scarcity messaging
"Focus on the CTA" - One clear action, contrasting button colors, action-oriented copy
"Follow the sequence" - Welcome, value delivery, social proof, conversion push
This conventional wisdom exists because it works—in theory. These tactics do improve open rates, click rates, and sometimes even conversion rates. The problem? Everyone is following the exact same playbook.
The result? Inboxes flooded with identical-looking emails that all sound like they were written by the same marketing automation software. Users have developed "template blindness"—they can spot a drip campaign from miles away and mentally tune out before reading the first line.
Even worse, these "best practices" optimize for metrics that don't always correlate with business results. You might get a 2% higher click rate, but if those clicks don't convert to meaningful engagement or sales, you're just burning your sender reputation for vanity metrics.
The biggest issue I see with traditional onboarding drip campaigns? They treat symptoms, not causes. They assume the problem is lack of awareness or motivation, when often the real issue is friction, confusion, or unaddressed concerns that no amount of "compelling copy" can solve.
Consider me as your business complice.
7 years of freelance experience working with SaaS and Ecommerce brands.
When I started working on this Shopify client's abandoned checkout emails, I had every intention of following the standard approach. Update the branding, maybe tweak the copy, add some urgency elements, and call it done.
The client was a B2C e-commerce store with a decent-sized product catalog. Their existing abandoned cart sequence was textbook perfect: clean design, prominent product images, "Don't let these items get away!" messaging, and a big bright "Complete Your Order" button.
But the conversion rates were mediocre at best. More importantly, through conversations with the client, I discovered a critical pain point that the emails completely ignored: customers were struggling with payment validation, especially with double authentication requirements.
Think about it—someone gets to checkout, encounters a technical hurdle with their bank's 2FA system, gives up in frustration, then receives a cheerful email asking them to "complete their purchase" with zero acknowledgment of why they might have abandoned in the first place.
That's when I decided to go completely against conventional wisdom. Instead of optimizing the existing template, I threw it out and created something that looked nothing like a typical e-commerce email.
The new approach was simple: What if this email came from an actual person who genuinely wanted to help, rather than a marketing department trying to push a sale?
I wrote the email in first person, as if the business owner was personally reaching out. I changed the subject line from "You forgot something!" to "You had started your order..." The design shifted from a product-focused template to a simple, newsletter-style layout that felt like a personal note.
Most importantly, instead of ignoring the elephant in the room, I addressed the actual friction points customers were experiencing.
Here's my playbook
What I ended up doing and the results.
Here's exactly what I implemented that transformed this abandoned checkout sequence from a standard drip campaign into a genuine customer service touchpoint:
Step 1: Persona Shift - From Brand to Human
I completely rewrote the email as if it was coming directly from the business owner. Not "The [Company Name] Team" but "Hi, it's [Founder Name] from [Company]." This wasn't just a copy change—it was a fundamental shift in how we approached automated communication.
The email started with: "I noticed you had started an order with us earlier but didn't complete it. I wanted to reach out personally because I know checkout can sometimes be frustrating with all the security steps these days."
Step 2: Address the Real Problem
Instead of pretending abandonment was about forgetting or changing minds, I tackled the actual technical issues head-on. I added a simple 3-point troubleshooting section:
Payment authentication timing out? Try again with your bank app already open
Card declined? Double-check your billing ZIP code matches exactly
Still having issues? Just reply to this email—I'll help you personally
Step 3: Design for Conversation, Not Conversion
I stripped out all the typical e-commerce email elements—product grids, multiple CTAs, promotional banners. Instead, I used a clean, newsletter-style layout with plenty of white space and a conversational flow.
The email looked more like something you'd receive from a friend than a marketing automation. This wasn't an accident—it was designed to break through the "promotional email" filter in people's brains.
Step 4: Make Response Easy and Human
Rather than just including a "Complete Purchase" button, I made it clear that customers could simply reply to the email if they needed help. This did two things: it positioned us as genuinely helpful rather than just sales-focused, and it gave us direct customer feedback about friction points.
The sequence became: Email 1 (immediate troubleshooting help) → Email 2 (if no response after 24 hours, simple check-in) → Email 3 (after 72 hours, last helpful touch with optional small discount).
Step 5: Track Engagement, Not Just Conversion
Instead of only measuring click-through rates and purchase completion, I started tracking email replies, the types of questions customers asked, and how many people used the troubleshooting tips successfully.
This data became invaluable for improving not just the email sequence, but the entire checkout process.
Real Solutions
Address actual friction points instead of ignoring them. Most abandonment isn't about motivation—it's about obstacles you can help remove.
Human Voice
Write as if you're personally reaching out, not as a faceless brand. People buy from people, even in automated sequences.
Reply Worthy
Make it easy and natural for customers to respond. Turn your drip campaign into a two-way conversation starter.
Smart Metrics
Track engagement quality, not just quantity. Email replies often predict lifetime value better than click rates.
The impact went far beyond just recovered carts—it fundamentally changed how customers perceived the brand:
Immediate Results:
Customers started replying to the emails asking questions (this never happened with the old template)
Some completed purchases after getting personalized help
Others shared specific issues we could fix site-wide
Unexpected Outcomes:
The email replies gave us direct insight into checkout friction we hadn't identified
Customer service quality improved because we were addressing problems proactively
Brand perception shifted from "another online store" to "people who actually care"
But here's what surprised me most: the approach worked because it acknowledged that abandonment usually isn't about lack of interest—it's about encountered obstacles.
By treating the email as a customer service tool rather than just a sales recovery mechanism, we created genuine value for people whether they completed their purchase or not. This relationship-first approach had ripple effects throughout the customer journey.
What I've learned and the mistakes I've made.
Sharing so you don't make them.
This experience taught me seven critical lessons about onboarding and automated email sequences:
Convention is your competition - When everyone follows the same "best practices," being different isn't just creative—it's strategic advantage
Problems > Products - Address why people don't complete actions, don't just ask them to complete actions
Voice matters more than design - A personal tone in a plain template beats perfect design with corporate messaging
Friction can be a feature - Adding troubleshooting steps increased rather than decreased engagement
Replies are gold - Email responses give you customer insight worth more than conversion metrics
Service sells better than sales - Positioning emails as helpful rather than promotional improves both perception and performance
Automation can feel human - It's not about removing automation—it's about automating human-like communication
The key insight: Most businesses optimize their onboarding sequences for immediate conversion when they should optimize for relationship building. The companies that win long-term are those that use automation to scale genuine helpfulness, not just marketing messages.
When you shift from "How do we get them to buy?" to "How do we genuinely help them succeed?" the conversion often takes care of itself.
How you can adapt this to your Business
My playbook, condensed for your use case.
For your SaaS / Startup
For SaaS startups implementing this approach:
Address common onboarding obstacles in your welcome sequence
Write emails as if from your founder, not your marketing team
Include direct troubleshooting help for common setup issues
Make it easy for users to reply with questions or problems
For your Ecommerce store
For e-commerce stores adapting this strategy:
Acknowledge specific checkout friction in cart abandonment emails
Use newsletter-style design instead of promotional templates
Provide actual solutions to payment and shipping concerns
Track email replies as a key engagement metric