The counterintuitive welcome email sequence (that actually works)

Let's be honest: Your welcome sequence could probably be better. Harsh? A little. But if you're following the cookie-cutter advice floating around the internet, you're likely boring your subscribers to death or, worse, actively pushing them away.

I've been there. My first welcome sequence was a disaster. It was so "best practice" heavy that it reeked of corporate aftershave and desperation. I ended up with crickets, tumbleweeds, and a list full of people who'd rather watch paint dry than open my emails.

I finally learned that a well-crafted welcome sequence can be your secret weapon. It's the difference between building a community of engaged fans and shouting into the void.

So, let's dissect the welcome sequence—warts and all—so you can avoid my mistakes and build yours the right way.

The (counterintuitive) truth about welcome sequences

Forget everything you've heard about welcome sequences being a "warm hug" for your subscribers. They're not here for a hug. They're here because they think you can solve a problem.

Your job isn't to "welcome" them. It's to prove they made the right choice by trusting you with their email address.

Here's the framework I use now in my welcome sequence after years of trial and error:

  1. Deliver value so fast it makes their head spin
  2. Challenge their assumptions (yes, even if it's uncomfortable)
  3. Paint a vivid picture of transformation (but be brutally honest about the work involved)
  4. Prove you're not just another "guru" (by admitting your failures and showing your scars)
  5. Give them a backstage pass to your business
  6. Give them a reason to stay (hint: it's not about you)

Let's break this down, email by email. And remember, whether you're selling digital products, artisanal cheeses, or unicorn grooming services, these principles apply because they're about human psychology, not industry specifics.

Email #1: The "Holy Sh*t" email

Forget the polite "Welcome aboard!" opener. Hit them with value so fast and hard that they have no choice but to pay attention.

Example

Subject: "The 2-minute tweak that doubled my client's revenue"

Body: "Most 'gurus' will tell you that increasing your digital product sales is all about better copywriting or fancier funnels. They're wrong. Here's the truth: I increased my client's revenue by 127% with a single, 2-minute change to their checkout process. It's not sexy, but it works. Here's exactly how we did it..."

Why this works: You're immediately proving your worth. No fluff, no BS, just pure, actionable value. You're also challenging the prevailing wisdom, positioning yourself as a straight-shooter who prioritizes results over hype.

Email #2: The "Uncomfortable Truth" email

Now that you've got their attention, it's time to shake things up. A good way to do that is to challenge a deeply held belief.

Example

Subject: "Why most digital products are doomed to fail (and how to make sure yours isn't)"

Body: "Let's face it: Most [your industry] businesses are built on a foundation of lies. Lie #1: [Common misconception]. Lie #2: [Another industry myth]. Lie #3: [One more falsehood]. Here's the uncomfortable truth about why [your industry] businesses fail, and the three critical elements yours needs to succeed..."

Why this works: You're differentiating yourself from the crowd by being willing to call out industry BS. This builds trust and positions you as a thought leader. It's like being the kid who points out the emperor has no clothes—people might be shocked, but they'll respect your honesty.

Email #3: The "This Is Gonna Hurt" email

Okay—now it's time to paint a vivid picture of transformation—but with a twist. Instead of just highlighting the benefits, be brutally honest about the work involved.

Example

Subject: "The ugly truth about building a 6-figure digital product business"

Body: "I could tell you that creating a successful digital product is easy. That you'll be sipping piña coladas on a beach while the money rolls in. But I'd be lying. The truth? It's hard work. You'll lose sleep. You'll doubt yourself. You'll want to quit. But if you push through, here's what's waiting on the other side..."

Why this works: By being honest about the challenges, you build credibility and set realistic expectations. This attracts serious subscribers and weeds out tire-kickers.

Email #4: The "I Screwed Up" email

In this email, vulnerability is your secret weapon. Share a major failure and what you learned from it.

Example

Subject: "How I lost $50,000 on my first digital product launch (and what you can learn from my mistake)"

Body: "I thought I had it all figured out. I'd read all the launch playbooks. I'd studied the 'gurus'. I was ready to rake in the cash. Instead, I lost $50,000 and almost gave up on digital products altogether. Here's what went wrong, and the three critical lessons that turned everything around..."

Why this works: Sharing your failures makes you relatable and human. It shows that you're not just another 'expert' who's never faced adversity.

Email #5: The "Behind the Curtain" email

This email is one of my favorites. It's time to give your subscribers a peek behind the scenes and show them something they can't get anywhere else.

Example

Subject: "The $100K mistake I'm making right now (and why I'm doing it anyway)"

Body: "Most 'gurus' only show you their wins. Today, I'm going to show you a massive risk I'm taking in real-time. I'm investing $100K in a new digital product launch that goes against everything the 'experts' recommend. Here's exactly what I'm doing, why I think it'll work, and what I'll do if it fails spectacularly. I'm also attaching my actual project plan and financial projections. Use them, learn from them, and maybe avoid the mistakes I'm probably making..."

Why this works: This email does several powerful things:

  • It creates a sense of exclusivity by sharing insider information.
  • It demonstrates vulnerability and authenticity by sharing a current, risky venture.
  • It provides immense value by giving away real business documents.
  • It builds anticipation for future emails where you'll share the results.

Most importantly, it cements your status as a trusted adviser who's in the trenches, not some infallible guru.

Email #6: The "Choose Your Own Adventure" email

We're rounding out the Welcome sequence with a "choose your own adventure"-style email. Instead of pushing for a sale, give them a choice. Show them you're committed to their success, whether they buy from you or not.

Example

Subject: "Two paths diverged in a yellow wood... (Which will you choose?)"

Body: "You're at a crossroads. Path A: Keep piecing together free advice and hoping it all works out. Path B: Let me guide you step-by-step through building a digital product empire. There's no wrong choice. If you choose Path A, here are three free resources to help you on your journey. If you're ready for Path B, here's how we can work together..."

Why this works: By giving them a genuine choice and providing value regardless of their decision, you're proving that you genuinely care about their success.

Making your Welcome sequence work

A few things to remember (especially if you're new to sequences):

  1. Timing is everything: Space these emails 2-3 days apart. Any closer, you're a pest; any further, they'll forget who you are.
  2. Automate but personalize: Use Beehiiv to automate your sequence, but use merge tags to make it feel personal. "Hey {FirstName}!" is a great first step towards personalization.
  3. Mobile-friendly or bust: 60% of emails are opened on mobile. You're dead in the water if your emails look like War and Peace on a phone screen.
  4. Test, but don't obsess: A/B test your subject lines and CTAs, but remember—you're writing for humans, not algorithms.

Measuring success: The metrics that actually matter

Forget vanity metrics like open rates. Here's what you should be tracking:

  1. Engagement Rate: Are people replying to your emails? Aim for at least 1-2% of recipients engaging.
  2. Click-Through Rate: For emails with a call to action (CTA), you want at least a 2-3% CTR.
  3. Unsubscribe Rate: Counterintuitively, a slightly higher unsubscribe rate (0.5-1%) can be good – you're weeding out the tire kickers.
  4. Revenue Per Subscriber: The holy grail. Calculate this by dividing total revenue by number of subscribers.

Track these ruthlessly. If an email isn't performing, don't be precious—kill it and try something new.

Some final notes on Welcome sequences

Even though I've laid out a clear path, starting a welcome series can be hard. There are many steps, and you're bound to run into a few speed bumps along the way.

Maybe your first email will land in spam. Maybe your big reveal will fall flat. Maybe you'll get a flood of angry replies.

Don't panic. Here's your emergency toolkit:

  1. If deliverability tanks: Check your sender score, clean your list, and consider a re-engagement campaign.
  2. If engagement plummets: Your subject lines probably suck. Study companies outside your industry for fresh ideas.
  3. If you get angry replies: Celebrate. Seriously. It means you're saying something worth disagreeing with.

Remember, a "failed" welcome sequence is just a data point. Learn from it, iterate, and try again.

The bottom line

Creating a killer welcome sequence isn't about following best practices or copying what worked for someone else. It's about having the courage to be yourself, to challenge your industry's status quo, and to truly serve your audience—even if it means fewer subscribers but more true fans.

Now, go tear apart your welcome sequence. Be ruthless. Be authentic. And for the love of all that's holy, be interesting.