How to Automate Your Digital Product Sales and Make Money While You Sleep

Dec 23, 2025

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Start selling digital products and services with MiloTree for FREE!

If you're an online coach, course creator, or digital product seller, you've probably experienced this: You're working 35-45 hours a week managing sales, manually sending products, and personally following up with every customer. You're making some money, but you're completely burnt out. Sound familiar?

In my newest episode, I shared the exact automation strategy that helped our MiloTree customer Ava transform her business. She went from making $1,800 a month while working 45 hours a week to earning over $11,000 a month working just 9 hours a week.

The secret? She automated three key parts of her sales process using MiloTree. And in this post, I'm going to show you exactly what she automated and how you can set up the same system to sell digital products on autopilot.

Show Notes:

MiloTree Free Plan
MailerLite (recommended email service provider)
Goldmine Product AI Prompt
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The Problem: Manual Sales Are Killing Your Business Growth

Here's what's happening to most digital product creators. You've built amazing products—courses, coaching packages, memberships, digital downloads. You're getting some sales, but you're stuck in a manual sales cycle that looks like this:

Someone downloads your freebie → You manually add them to your email list → You manually send follow-up emails → You manually process orders → You manually deliver products → Repeat.

This manual process has three major problems:

Time Drain: You're spending hours every week on tasks that could be automated
Revenue Cap: You can only make as much money as the hours you can physically work
Burnout Risk: Eventually, managing everything manually becomes unsustainable

The good news? You can automate your entire sales process so your business runs without you working harder—you just work smarter.

The Solution: Three Types of Sales Automation That Actually Work

There are three powerful ways to automate your digital product sales: tripwires, order bumps and upsells, and email sequences. Let me break down each one and show you exactly how they work together to create a sales system that runs on autopilot.

1. Tripwires: Turn Freebie Seekers Into Buyers Instantly

A tripwire is a low-cost product (usually $7-$27) that you offer immediately after someone opts in to get your free lead magnet. Here's how it works:

Someone sees your content on social media → They click to download your free cheat sheet → They enter their email on your opt-in page → They land on the thank you page → Right there, they see an offer for your complete toolkit for just $17 → They click, they buy → MiloTree delivers the product automatically.

You do nothing. It all happens automatically.

The beauty of tripwires is that they convert freebie seekers into paying customers right away. Once someone has bought from you once, they're 9 times more likely to buy from you again.

2. Order Bumps and Upsells: Increase Average Order Value Without More Traffic

Here's where things get really powerful. Someone's already buying your $47 course. At checkout, you offer a $12 complimentary workbook with one simple checkbox. They tick the box—boom, they've added it to their order.

After they complete the purchase, they land on your thank you page. Now you offer them your $97 "done-for-you" premium version. With another click, they've purchased that as well.

You just turned a $47 sale into a $156 sale without getting a single additional customer.

Order bumps and upsells can increase your revenue by 30-50% without any additional marketing. You're simply maximizing the value of customers you're already getting.

3. Email Sequences: Build Relationships and Sell While You Sleep

This is the foundation that makes everything else work. An email sequence is a series of automated emails you set up once that go out to new subscribers automatically.

One of our MiloTree customers, Amanda, set up her main email sequence six months ago. That one sequence generates over $1,500 a month for her business, and she hasn't touched those emails since she initially created them.

Here's what a good email automation does:

Builds Relationships: Your subscribers get to know, like, and trust you through consistent communication
Delivers Value: You're providing helpful content that solves their problems
Sells Naturally: You're making offers that feel like helpful solutions, not pushy sales pitches

Email is one of the best channels for sales. For every $1 you spend on email marketing, you typically make about $36 in return. That's a 3,600% ROI.

Why You Can't Do Email Marketing Through Gmail (And What You Need Instead)

Here's something crucial to understand: You cannot do email marketing through Gmail, Yahoo, or any regular email account. You need what's called an email service provider (ESP).

An email service provider is a platform like MailChimp, MailerLite, Kit, or Flodesk. It's built specifically for business email marketing. Here's what ESPs do that regular email can't:

Deliverability: They get your emails into people's inboxes instead of spam folders
Analytics: They track who opens your emails, who clicks links, and who buys
Segmentation: They let you organize subscribers based on their interests and behavior
Automation: They let you set up those money-making email sequences we talked about

My favorite email service provider is MailerLite. We use it ourselves for MiloTree's email marketing. I recommend it for three reasons:

Free to Start: You get your first 1,000 subscribers completely free
User-Friendly: It's the easiest ESP I've used—intuitive drag-and-drop design
Seamless Integration: It works perfectly with MiloTree for automated product delivery

MiloTree integrates with 24 email service providers, including MailChimp, Kit (formerly ConvertKit), Flodesk, ActiveCampaign, MailerLite, Klaviyo, and many others. We're always adding new integrations based on customer requests.

But if you're just starting out and asking me what to try first, I'd go with MailerLite.

How MiloTree and Your Email Service Provider Work Together

Let me show you the exact flow of how MiloTree and your email service provider work together to automate your sales. This is where the magic happens.

Here's the complete automated workflow:

Step 1: Someone sees your content on Instagram, TikTok, Pinterest, or your blog

Step 2: You offer a lead magnet (a free download, cheat sheet, template, etc.)

Step 3: They click and land on your MiloTree opt-in page where they enter their name and email

Step 4: MiloTree captures that email and automatically sends it to your email service provider

Step 5: MiloTree instantly delivers the freebie to your new subscriber on the thank you page—they can download it immediately

Step 6: At the same time, MiloTree sends a "tag" to your email service provider

Step 7: That tag triggers your automated email sequence to start

Step 8: Your welcome sequence begins—usually 5-7 emails that go out over the next week

Step 9: These emails build the relationship, provide value, and make offers

Step 10: When someone clicks to buy, MiloTree processes the payment and delivers the product automatically

You do nothing. It all runs on autopilot.

The Power of Tags: How to Trigger Different Email Sequences

Here's what makes this system so powerful: tags. A tag is simply a label you assign to a subscriber based on what they've downloaded or purchased.

Let's say you have three different freebies:

A "Social Media Content Calendar" (tagged: social-media-freebie)
A "Product Launch Checklist" (tagged: launch-freebie)
An "Email Marketing Guide" (tagged: email-freebie)

When someone downloads your Social Media Content Calendar, MiloTree automatically tags them with "social-media-freebie" in your email service provider. That tag triggers your social media email sequence.

The beauty of this system is that different freebies can trigger different email sequences. Someone interested in social media gets emails about social media. Someone interested in email marketing gets emails about email marketing.

You're sending the right message to the right person at the right time—all automatically.

How to Set Up Your MiloTree and Email Service Provider Integration in 2 Minutes

Setting up this automation sounds complicated, but it literally takes about two minutes. Let me walk you through it step by step.

Step 1: Log into your MiloTree dashboard at milotree.com

Step 2: Click on "Email Integration" in the menu

Step 3: Select your email service provider from the dropdown menu (MailerLite, MailChimp, Kit, etc.)

Step 4: Follow the simple connection instructions—every platform is slightly different, but we have step-by-step guides for each one

Step 5: Test the connection to make sure it's working

That's it. Now every time someone opts into your freebie, their email automatically flows into your email service provider and triggers your automated sequence.

If you have any trouble with the setup, just email me at jillian@milotree.com and I'll personally help you get it working.

Your Action Plan: Set Up Your Automated Sales System Today

Here's exactly what I want you to do right now to start automating your sales:

First, if you don't have an email service provider yet, sign up for one. I recommend MailerLite to start because it's free for your first 1,000 subscribers and it's incredibly user-friendly.

Second, sign up for MiloTree if you haven't already. Start with our free plan to test everything. You can create a freebie opt-in page for free, sell a product for free, and see how the system works. Then when you're ready to scale, upgrade to one of our paid plans to run your entire digital product business with MiloTree.

Third, connect MiloTree to your email service provider using the two-minute process I outlined above. Don't worry if you get stuck—just reach out and we'll help you.

Fourth, create your first lead magnet if you don't have one yet. Download my free AI prompts that will help you create an irresistible freebie in about 10 minutes: The 3 AI Prompts You Need to Create a Freebie Cheatsheet

Fifth, set up your welcome email sequence. This is the series of 5-7 emails that will build relationships and make sales automatically.

Why MiloTree Makes Selling Digital Products Easier Than Any Other Platform

At MiloTree, we built our platform specifically for coaches, course creators, and digital product sellers who want to automate their sales without dealing with complicated tech.

Here's why creators love MiloTree:

All-in-One Platform: Sell digital products, offer unlimited freebies, grow your email list, process payments, and deliver products—all from one simple dashboard

No Tech Skills Required: Our AI tools help you create opt-in pages, sales pages, and checkout pages in minutes, not days

Start Free: Test everything with our free plan—no credit card required. Create opt-in pages, deliver freebies, and see how the system works before you upgrade

Affordable Pricing: Our paid plans start at just $9/month and grow with your business. No surprise fees or complicated pricing tiers

Built for Creators: Unlike generic ecommerce platforms, MiloTree is designed specifically for digital product creators, so everything is streamlined for your needs

Integrates With Everything: We connect with 24 email service providers, plus all major payment processors

Personal Support: When you have questions, you can email me directly at jillian@milotree.com and I'll help you personally

👉 Ready to automate your sales and grow your digital product business? Sign up for MiloTree's free plan and start creating beautiful opt-ins and selling digital products today—it's simple, affordable, and effective.

What to Do After You've Set Up Your Infrastructure

Okay, so now you've got the infrastructure in place. You've connected your email service provider to MiloTree. You've set up your freebie. But here's what you need next: the actual emails.

What do you say in those automated emails? How many should you send? How do you build trust while actually selling?

That's exactly what I'm covering in my next podcast episode. I'm giving you an AI prompt that will write your entire welcome series in about 10 minutes—a series that will make you money on autopilot.

In the meantime, make sure you're getting value from every subscriber by understanding the psychology of why people buy. Download my 6 Purchasing Triggers guide to learn exactly what motivates your audience to purchase.

Final Thoughts: Automation Isn't About Working Less—It's About Working Smarter

Here's what I want you to understand: Automation isn't about being lazy or removing the human element from your business. It's about working smarter so you can focus on what matters most—creating great content, serving your customers, and growing your impact.

When Ava automated her sales process, she didn't just make more money ($11,000 vs. $1,800 per month). She got her life back. Instead of working 45 hours a week on manual tasks, she works 9 hours a week on strategic activities that actually grow her business.

She has time to create better products. She has time for her family. She has time to live her life instead of being chained to her inbox.

That's what proper automation gives you: freedom and growth at the same time.

The time to start is now. Set up your infrastructure today, and in a few weeks, you could have an automated sales system that generates revenue while you sleep.

Your future self will thank you.

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