AI & Automation
Personas
SaaS & Startup
Time to ROI
Short-term (< 3 months)
You know what's funny? I was working on a complete website revamp for a Shopify e-commerce client last year, and 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. And that's when I realized we had a much bigger problem than brand consistency.
Most businesses are obsessing over the perfect onboarding email sequence while completely missing the point. They're crafting these elaborate 7-email journeys that sound like they were written by a committee of marketers, not actual humans. The result? Email sequences that get ignored, deleted, or worse—marked as spam.
Here's what you're going to learn from my experience of completely reimagining onboarding emails:
Why making your emails feel like personal conversations beats polished templates every time
The specific changes I made that doubled email reply rates for a Shopify client
How addressing real customer problems in emails transforms them from marketing messages into customer service touchpoints
The counterintuitive approach to subject lines that actually gets emails opened
A simple framework you can apply to any business to create onboarding sequences that people actually want to receive
This isn't about optimizing open rates or click-through percentages. It's about fundamentally changing how you think about what an onboarding email should do. Check out our email marketing strategies and SaaS onboarding optimization guides for more insights.
Industry Reality
What every marketer thinks they know about email sequences
Walk into any marketing conference or browse through industry blogs, and you'll hear the same advice repeated everywhere. The conventional wisdom for onboarding email sequences follows a predictable pattern that most businesses copy without thinking.
Here's what the industry typically recommends:
Welcome email with company branding - Polished templates with your logo, brand colors, and formal welcome message
Product education sequence - A series of emails explaining features, tutorials, and how-to guides
Social proof injection - Testimonials, case studies, and customer success stories scattered throughout
Urgency and scarcity tactics - Limited-time offers, countdown timers, and "Don't miss out" messaging
Segmentation by user behavior - Different email paths based on clicks, opens, and engagement metrics
This approach exists because it's measurable, scalable, and feels "professional." Marketing teams love it because they can A/B test subject lines, track conversion funnels, and present clean metrics to management. It's the kind of strategy that looks great in PowerPoint presentations.
But here's where it falls short in practice:
These sequences treat customers like data points in a funnel rather than actual humans with real problems. They focus on pushing features instead of solving immediate pain points. Most importantly, they sound exactly like every other automated email sequence your customers receive—which means they get ignored.
The biggest issue? They optimize for metrics that don't matter. High open rates mean nothing if people delete your email after reading the first line. Click-through rates are meaningless if users don't actually engage with your product. When everyone follows the same playbook, the playbook becomes noise.
Consider me as your business complice.
7 years of freelance experience working with SaaS and Ecommerce brands.
So there I was, staring at this template that looked like it came from a "Best Email Marketing Practices" handbook. The client was a Shopify e-commerce business selling products with a decent price point—not impulse purchases, but considered buys where customers needed some reassurance.
Their existing abandoned cart sequence was working "fine" in terms of industry benchmarks. Decent open rates, acceptable click-through rates, the usual metrics that make marketing managers feel good about their campaigns. But something was bothering me about the whole approach.
The first red flag was the tone. Every email sounded like it was written by a corporate marketing department. "Dear valued customer," followed by product grids and discount codes. It was professional, polished, and completely forgettable. The kind of email you scan for two seconds before hitting delete.
But the real problem became clear when I dug deeper. Through conversations with the client, I discovered a critical pain point that their standard emails completely ignored: customers were struggling with payment validation, especially with double authentication requirements. People were getting frustrated during checkout, abandoning their carts, and then receiving generic "You forgot something!" emails that didn't acknowledge their actual problem.
This client was losing customers not because of price or product issues, but because of technical friction that their email sequence pretended didn't exist. Their beautifully designed templates were optimized for everything except helping customers overcome the real barriers to purchase.
My first instinct was to improve the existing framework. Better subject lines, more compelling calls-to-action, maybe some personalization tokens. But then I realized we were approaching this completely backwards. Instead of trying to optimize a flawed system, what if we started from scratch with a completely different philosophy?
That's when I decided to throw out the marketing playbook entirely and treat the abandoned cart email like what it should actually be: a helpful message from a real person who genuinely wants to solve the customer's problem.
Here's my playbook
What I ended up doing and the results.
Instead of tweaking the existing template, I completely reimagined the entire approach. The breakthrough came when I stopped thinking like a marketer and started thinking like a customer service representative.
Here's exactly what I implemented:
1. Ditched the Corporate Template for Newsletter-Style Design
I threw out the traditional e-commerce email template with product grids and prominent CTAs. Instead, I created something that looked and felt like a personal newsletter. Clean, text-focused, with plenty of white space. The kind of email you'd actually want to read, not just scan for discount codes.
2. Rewrote Everything in First Person
Instead of "The [Company Name] Team" sending automated messages, the email came directly from the business owner. Not a fake persona, but the actual person running the business. The entire tone shifted from corporate communication to personal conversation.
3. Changed the Subject Line Strategy
Out: "You forgot something!" or "Complete your order now"
In: "You had started your order..."
That subtle change transformed the entire relationship. Instead of accusatory or pushy, it became conversational and understanding. Like a friend gently reminding you about something you mentioned.
4. Addressed the Real Problem Head-On
This was the game-changer. Instead of ignoring the payment friction, I made it the focus of the email. 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
5. Made It Actually Reply-Friendly
Most abandoned cart emails are sent from no-reply addresses. I made sure this email invited responses and actually meant it. The business owner was prepared to personally help customers who replied with issues.
6. Removed All Sales Pressure
No countdown timers, no "Limited time offer!" messaging, no artificial urgency. Just genuine helpfulness. The email's primary goal was solving problems, not pushing sales. The assumption was that if we solved the customer's actual problem, the sale would happen naturally.
The entire email read like a personal note from someone who actually cared about the customer's experience, not like a marketing automation trying to extract revenue.
Customer Psychology
Understanding why people abandon carts and addressing those specific pain points rather than generic follow-ups
Personal Branding
Emails from real people get responses. Corporate templates get deleted. Simple as that.
Problem-First
Lead with the customer's actual problem before trying to sell them anything
Response Strategy
Always invite replies and be prepared to actually help when customers respond
The impact went way beyond just recovered sales. Within two weeks of implementing this approach, something remarkable happened: customers started replying to the emails.
Not just clicking through to complete purchases, but actually responding with questions, feedback, and requests for help. The abandoned cart email had transformed from a sales tool into a customer service touchpoint. Some customers completed their purchases after getting personalized help, while others shared specific issues that helped improve the overall site experience.
The quantitative results were solid: Email reply rates doubled compared to the previous template, and cart recovery improved by a meaningful margin. But the qualitative impact was even more significant. The business owner was suddenly having direct conversations with customers who had previously just disappeared.
Several customers mentioned that they almost never reply to business emails, but this one felt different. "It felt like you actually cared about helping me," one customer wrote back. Another said, "I was surprised to get such a personal response—most companies just spam you with the same product photos."
The email became a diagnostic tool for identifying site-wide issues. Multiple customers replied mentioning the same payment authentication problems, which led to implementing site improvements that benefited all future customers, not just the ones who abandoned carts.
Most importantly, it changed the entire relationship dynamic. Instead of trying to push reluctant customers toward a purchase, the business was now positioned as a helpful partner solving real problems. That shift in perception extended far beyond the abandoned cart sequence.
What I've learned and the mistakes I've made.
Sharing so you don't make them.
Here are the key lessons I learned from completely reimagining the onboarding email approach:
Authenticity beats optimization every time. A genuine, helpful email from a real person will always outperform a perfectly optimized template that sounds like everyone else's template.
Address real problems, not marketing problems. Instead of focusing on "low conversion rates," focus on why customers are actually struggling. The business problem and the customer problem aren't always the same thing.
Personal beats professional in email. Newsletter-style design and conversational tone consistently outperform polished corporate templates. People want to feel like they're talking to a human, not receiving automated marketing.
Subject lines should feel natural, not optimized. "You had started your order..." sounds like something a friend would say. "Complete your purchase now!" sounds like spam.
Make replies a feature, not a bug. Most businesses try to avoid email responses. I learned that customer replies are actually valuable feedback and relationship-building opportunities.
Remove sales pressure to increase sales. Counterintuitively, focusing on helping rather than selling led to better conversion outcomes.
One great email beats seven mediocre ones. Instead of complex multi-email sequences, one genuinely helpful message often performs better.
The biggest learning? In a world of automated, templated communications, the most powerful differentiation might just be sounding like an actual person who cares about solving problems rather than just completing transactions.
This approach works best for businesses where customer relationships matter more than transaction volume, and where there's a real person behind the brand who can engage authentically with customers.
How you can adapt this to your Business
My playbook, condensed for your use case.
For your SaaS / Startup
For SaaS businesses:
Address common onboarding friction points directly in emails
Write emails from the founder, not the "team"
Focus on solving user problems, not showcasing features
Invite support replies and actually respond personally
For your Ecommerce store
For E-commerce stores:
Address checkout and payment issues directly in cart recovery emails
Use newsletter-style design instead of product-heavy templates
Write in first person from the business owner
Remove sales pressure and focus on customer service