Sales & Conversion
Personas
SaaS & Startup
Time to ROI
Short-term (< 3 months)
OK, so you know how everyone's obsessing over the perfect onboarding email sequence? The welcome email, the feature tour, the "did you complete your setup?" reminder—all that stuff that's supposed to guide users through your product like they're five years old.
I used to build those too. Spent hours crafting the "perfect" 7-email sequence that would walk new users through every feature. But here's what I discovered working with a Shopify e-commerce client: the most effective onboarding email I ever wrote looked nothing like an onboarding email.
Instead of the typical "Welcome to our platform!" template, I wrote something that felt like a personal note from the business owner. No corporate speak, no feature lists, just a human being reaching out to help solve actual problems. The result? Customers started replying to ask questions, some completed purchases after getting personalized help, and others shared specific issues we could fix site-wide.
Here's what you'll learn from my experiment with newsletter-style onboarding:
Why traditional onboarding emails feel transactional (and how to fix that)
The specific changes that turned abandoned cart emails into conversations
How addressing real friction points beats generic feature tours
The psychology behind why personal emails outperform automated sequences
A step-by-step framework for humanizing your entire email strategy
This isn't about abandoning automation—it's about making automation feel human. Let's dive into why most SaaS onboarding misses the mark and what actually works in 2025.
Industry Reality
What every startup founder has been told about onboarding
If you've read any growth blog in the last five years, you've probably seen the same onboarding email advice repeated everywhere. It goes something like this:
The "Best Practice" Checklist:
Welcome email with brand guidelines and expectations
Feature tour sequence explaining every button and menu
Progress reminders pushing users to "complete their setup"
Social proof emails with testimonials and case studies
FOMO-driven emails about features they're "missing out" on
This approach exists because it's logical. You want users to understand your product, see its value, and stick around. The problem? Logic doesn't create emotional connection.
Most onboarding sequences treat users like they're going through airport security—efficiently processed through predetermined checkpoints. Email 1: Welcome. Email 2: Setup. Email 3: First action. It's systematic, measurable, and completely forgettable.
The issue isn't that these emails don't work—they do convert some users. The issue is they miss the bigger opportunity. When someone signs up for your product, they're not just adopting software; they're looking for a solution to a real problem in their business or life. But instead of addressing that human reality, we send them feature lists.
What's missing is the recognition that onboarding isn't about your product—it's about their problem. This is where my approach takes a completely different turn.
Consider me as your business complice.
7 years of freelance experience working with SaaS and Ecommerce brands.
The realization hit me while working on email updates for a Shopify e-commerce client during a complete website revamp. The original brief was simple: update the abandoned cart emails to match the new brand guidelines. New colors, new fonts, done.
But as I opened their old template—with its product grid, discount codes, and "COMPLETE YOUR ORDER NOW" buttons—something felt wrong. This looked exactly like every other e-commerce store's emails. Generic, transactional, and easy to ignore.
Through conversations with the client, I discovered a critical pain point their customers were experiencing: payment validation issues, especially with double authentication requirements. Most businesses would ignore this friction, but I saw an opportunity.
What I realized: Instead of sending another "You forgot something!" email, what if we actually helped solve the problems people were having?
So I completely reimagined the approach. Instead of a traditional e-commerce template, I created a newsletter-style design that felt like a personal note. I wrote it in first person, as if the business owner was reaching out directly. The subject line changed from "You forgot something!" to "You had started your order..."
But here's the key part—I added a simple 3-point troubleshooting list:
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
The transformation was immediate. Instead of just trying to push the sale, we were actually solving problems. The email became a customer service touchpoint, not just a sales tool.
Here's my playbook
What I ended up doing and the results.
Here's exactly how I transformed a standard transactional email into a conversation starter, step by step:
Step 1: Ditch the Corporate Template
Instead of the typical e-commerce email layout, I designed something that looked like a newsletter. Clean, simple, personal. No product grids or flashy graphics—just a message from one human to another.
Step 2: Write in First Person
Every email was written as if the business owner was personally reaching out. No "Our team" or "We at [Company Name]"—just "I noticed you started an order..." This immediately changes the entire dynamic.
Step 3: Address Real Friction Points
Instead of ignoring checkout problems, I made them the centerpiece. If customers are struggling with payment validation, why not acknowledge that and help? I researched the most common checkout issues and created simple troubleshooting steps.
Step 4: Invite Conversation
This was the game-changer. Instead of ending with "Shop Now," I ended with "Just reply to this email if you need help." Suddenly, a one-way marketing message became a two-way conversation.
The Technical Implementation:
I set up the email sequence in their existing platform but changed the entire approach:
Trigger: 1 hour after cart abandonment (not immediately)
Design: Newsletter template, not e-commerce template
Copy: Personal, helpful, conversational
CTA: "Reply for help" alongside "Complete order"
The most important part was the mindset shift. This wasn't an automated sales email anymore—it was automated customer service. We were using automation to scale personal attention, not replace it.
This approach works because it acknowledges what most businesses ignore: people abandon carts for reasons beyond "they forgot." They get confused, frustrated, or stuck. Instead of pretending these problems don't exist, we addressed them head-on.
Key Insight
Personal touch beats perfect automation every time
Troubleshooting Focus
Address real problems instead of promoting features
Conversation Starter
End emails with questions, not just purchase buttons
Human Automation
Use automation to scale personal attention, not replace it
The impact went beyond just recovered sales. Within the first month of implementing this newsletter-style approach:
Customer Engagement Changed:
Customers started replying to emails asking questions
Some completed purchases after getting personalized help
Others shared specific issues we could fix site-wide
Email replies became a source of product feedback
But the most significant change wasn't measurable in traditional metrics. The entire relationship between the business and customers shifted. Instead of sending marketing messages into the void, they were having actual conversations with real people.
The abandoned cart email became a customer support channel. Customers would reply with questions about shipping, sizing, product details—things they might have searched for and not found on the website. This feedback loop helped improve the entire customer experience.
What surprised me most was how this approach reduced support tickets while increasing customer satisfaction. By proactively addressing common problems in the email, customers could solve issues themselves without needing to contact support.
What I've learned and the mistakes I've made.
Sharing so you don't make them.
Here are the key insights from this experiment that you can apply to any onboarding sequence:
1. People Want Help, Not Hype
When someone signs up or abandons a cart, they're not looking for more marketing. They want solutions. Address actual problems instead of listing features.
2. Personal Beats Perfect
A slightly imperfect email that feels human will outperform a perfectly designed template that feels corporate. People buy from people, not companies.
3. Invite Conversation Early
Don't wait until customers have problems to open communication channels. Make it easy for them to reach out from the first email.
4. Address Friction Head-On
Every business has common customer problems. Instead of hoping they'll go away, acknowledge them and provide solutions proactively.
5. Automation Should Feel Personal
The goal isn't to eliminate human touch—it's to scale it. Use automation to deliver personal attention to more people.
6. Design for the Platform
Email design should feel native to email, not like a website squeezed into an inbox. Newsletter layouts often work better than traditional marketing templates.
7. Test Against Conventional Wisdom
Sometimes the best solution is the opposite of what everyone else is doing. Don't follow best practices blindly—test contrarian approaches.
How you can adapt this to your Business
My playbook, condensed for your use case.
For your SaaS / Startup
For SaaS products, implement newsletter-style onboarding by:
Writing welcome emails as personal notes from the founder
Addressing common setup frustrations proactively
Ending emails with "Reply if you're stuck" instead of feature links
Sharing why you built the product, not just how to use it
For your Ecommerce store
For e-commerce stores, create conversational emails by:
Acknowledging checkout friction instead of ignoring it
Including troubleshooting tips for common payment issues
Writing cart abandonment emails as helpful check-ins
Using newsletter templates instead of traditional promotional layouts