Email Drip Campaigns and Autoresponders: The Ultimate Guide

Complaining about marketing emails is all the rage right now:

I just spent an hour trying to unsubscribe from all the junk mails. It’s like trying to empty the ocean with a teaspoon. — Tanis Miller (@redneckmommy) September 6, 2014

Is there a button I can hit to unsubscribe from every junk email I get? Seriously urban outfitters, I’ve unsubscribed 10 times. STOP. — Stephen Gomez (@stephen_james) September 10, 2014

I agree. And I thank Google every time I click on my promotions tab and see a mountain of marketing emails from a ton of drip campaigns that I can archive in one swoop.

But let me say this:

There are a few companies that I love getting emails from. I open them within seconds. I use it as a break from work. It’s unproductive. It’s a waste of time. I get it.

But here’s the thing: I know they send me cool stuff. I even know they’re trying to sell me something.

I. Don’t. Care.

I like their product, I like their design, or I like their advice. Or maybe all 3.

And I bet it’s true for you too.

Because here’s the thing..

…it’s only a select few companies…the rest get archived en masse, regardless of which tab they show up in.

So what’s the difference between those terrible emails and the companies whose emails I open with the same guilty satisfaction as checking TMZ ESPN?

Simple: they aren’t just pumping advertising down my throat like I’m some factory farmed chicken. For example, check out this email I got from Buy.com after I bought some random gadget:

Apparently I might have been interested in a sandwich maker, 2 smoke alarms, or Lego Pirates of the Caribbean. Hey, you never know.

Here’s the worst part. Check out how often I was getting these emails from them:

Apparently in the summer of 2011, I was getting one to two emails every day. These emails were just ads. And on June 8th, I came to my senses and unsubscribed.

But when I happened to buy some random thing in 2012, I was back on their list. Then I unsubscribed again, and again in 2013 I bought something.

What is happening here?

Every time I buy, I’m being put on an email drip campaign, or autoresponder.

What is a Drip Campaign (or Autoresponder) and What is this Guide?

It’s just a series of automated messages that are sent out when someone signs up, buys or does something on a website or app.

In this case we’re talking about drip campaigns sent out by email.

The reason email campaigns are so important is because (despite all the complaints about bad marketing emails) email engagement rates are really high compared to other channels like Facebook and Twitter.

This is why companies keep pumping our inboxes with these promos…even though we hate it.

Someone at Buy.com marketing noticed that every time they send out a promo email, some fraction of people buy something. Then their boss asked them to sell more product. The answer? Send more promo emails!

But what about the emails I look forward to? What are they doing right?

It’s simple:

They actually send me things I want to read. Things that add value to me. So I open them. I read them. I click. And sometimes (rarely…but sometimes) I buy.

But here’s the sad part…

There are so many awesome companies that could send me awesome emails. But they spam me with ads (ahem, Buy.com).

Let me give you some examples.

Evernote, the app with so much potential for awesome emails

I love Evernote. I use it all day, every day. There are so many creative ways to use it, so I know I could be using it even better. I’d love to read detailed case studies of how other power users use it. I want to become a master at it. In fact, if they emailed me and asked me to be some kind of ambassador, I’d do it.

And their emails almost, kind of, sort of, just maybe look like they could be adding value, but in the end they are just promotions.

“Upgrade to business.” “Buy this random accessory that only hipsters use.” “Have you upgraded to our business plan yet?”

Archive.

I’m not sure, but I think they want me to Shop the Evernote Market.

Note in this screenshot, from December to May they sent just one email with tips, but even when I opened that one, it turns out it was an ad for a scanner with a green “shop now” button.

There are so many cool things they could send me that I would love (outlined below). But they don’t, they just send ads.

So even though I love Evernote and use it all day every day, I have yet to upgrade to a paid subscription. Too bad.

20Jeans, the fancy jeans site that only sends me promotions

I bought some “raw denim” jeans from them that I love. I talk about it all the time. I was happy to be that indy kid who discovers the new band before they hit MTV.

Obviously their customers care about clothes, how they look, and how to dress. I’d love to see what other people are wearing with their jeans and how they’re taking care of them. Other tips on dude fashion (yes, you can judge me). But what do they send me? Promotions. Deals. Buy more! Buy more!

At first, they did send me a couple of great emails right off the bat but then it turned into a steady stream of ads.

I wasn’t planning on buying anything, but thanks for the free shipping.

I couldn’t take it. I’ve now unsubscribed, even though I was an ideal customer ready to love them and buy from them for years (more email screenshots below).

What Should These Companies Be Sending Instead?

They should be sending emails that are actually useful, valuable, fun, funny, or entertaining to the recipient.

Basically, they should do what every business book has recommended since cavemen started writing on walls: add some frickin’ value.

And (this will make CMOs gasp across the world) they shouldn’t ask for a sale in every email of their drip campaign. In fact, I’d recommend they not ask for a sale in most drip emails or autoresponders.

Here are 2 reasons why:

1. The investment in long term relationships makes sense here – Autoresponders are created once, then sent over and over again to thousands of subscribers. So you don’t need to get a huge ROI on every email. You have a unique opportunity to get your subscriber, customer, or prospect to love you; to love getting emails from you; to trust what you have to say. So later, when you do have something to sell, that trust is established.

That’s not true of a single marketing email blast. There you have to use designer, copywriter, and sales time, and you get only one email out of it. So if you want to hard sell some product to get your money back, be my guest. It’s only going to be sent once.

But a drip campaign is sent over and over again. So it’s the most logical place to invest in building trust with your subscriber.

Gary Vaynerchuck discusses this same strategy for social media, and it applies to email marketing as well.

2. They are triggered by the customer engaging with you, don’t blow it here – In the vast majority of the cases, drip campaigns are triggered by the customer doing something with you: buying, subscribing, signing up. At that moment, the customer is on a high. They have confirmation bias. They want to believe you are awesome and they made a great decision.

So don’t blow it!

Sending them a series of promo emails asking them to buy is literally like following up a good first date with 17 text messages asking for the second. Don’t be that desperate.

The “Will They Miss Me” Test

If you’re still not sure what is valuable, use the test made famous by Seth Godin’s thoughts on permission marketing:

…if you stop showing up, people complain, they ask where you went.

Hold your emails to that standard. Will your readers miss you if you stop arriving in their inbox?

Techniques to Add Value in Email Marketing

“Ok Devesh, add value. Got it.”

Most blog posts will have “add value” as one item on their top 10 list, and you will nod and move on to the rest of your Twitter feed.

Not here.

Here I’m going to answer this question in detail for you: How?

What can you put in your drip campaign or autoresponder that shows you care about the person receiving it more than the person sending it?

Here are exact ways you can add value, whether you’re an e-commerce company, a business app, another SaaS app, or a blogger with an info product. You can use these exact techniques today and watch your engagement rates skyrocket.

Add Value Technique #1: Send Case Studies

If you don’t have good case studies to send to your readers you’re either a) too early to be doing email marketing or b) have a crappy product that’s not helping anyone. In either case, this guide is probably not for you.

Otherwise, know that case studies are the single easiest way to add massive value to your readers.

If I give you my email address, it means I have some real interest in what you’re saying or selling. But when I first give you my email, I’m still a little skeptical. Excited, but anxious. Aren’t you?

• E-commerce: “I hope these jeans are good!”
• Blogs and Infoproducts: “That was a good article, I hope she sends more like that.”
• Apps and SaaS: “Man, I really hope this app solves my problem.”

How nice would it be to get some case studies of people, just like you, right off the bat? I, for one, would love it:

• E-commerce: 10 awesome outfits that buyers of these jeans put together for any occasion
• Blogs and Infoproducts: How Larry, a fellow reader of the blog used [this exact advice] to get [this exact result that you’re looking for]
• Apps and Saas: How Samantha, a small business owner just like you, uses our app to save 4 hours a week of admin headache.

I would open each of those emails if I had just signed up…with a smile on my face. Why? Because in each case there is some benefit to me:

• I just bought your clothing, so yes, I want to know that someone like me looks good in it.
• I just signed up for your mailing list so I have some need for your advice. Oh, Larry used it to get the results I want? Perfect, tell me about him.
• I just signed up for your app’s free trial, so obviously I want to make sure it solves some problem of mine. Samantha saves how much time with it? Wow, I want to know exactly how she did it.

Here’s a great case study email from SEO expert Brian Dean of Backlinko:

Obviously anyone on Brian’s email list wants to get more traffic and conversions.

But his readers may have barriers that SEO and conversion optimization is too complicated, too costly, only for techies, or whatever. So Brian sends an email about how two normal business owners, just like me, are using one of his techniques to get more opt-ins. I’m all ears.

Add Value Technique #2: Send Useful Instructions and How to Get Started

Many apps, products, or techniques are complicated.

Think of the first time you saw the “dashboard” of some business or productivity app (or even your online bank). What’s the first thing you think? “Ok, let’s see…How do I use this? Where do I start?….hmm…maybe if I click here?…no…ah forget it, I’ll learn it later. Let’s see what’s on Twitter…”

That happens to me all the time. Literally using any app for me is like revisiting the first moment I opened Photoshop:  Get scared. Close photoshop. Open MS Paint. Feel bad about myself.

When you feel like that (and we all do), how nice is it to get an email right then that says “Hey! This is exactly where you start.”? Answer: It’s really nice.

And this is true beyond just apps. Products can be complicated too. When I ordered those fancy “raw denim” jeans and got an email about how to care for them and wash them, you can bet I read that email. I bookmarked it. If it was still 1993, I would have printed it. In fact, here’s a part of it:

Does this email get me to buy again? No. But that’s not the point. I JUST BOUGHT! I don’t want to buy again. I want to appreciate and love what I just bought.

Do that successfully and I’ll buy over and over again for years to come. And I’ll tell my friends how awesome your company is.

This even works for bloggers who aren’t immediately selling anything.

If you run into a blog that has the perfect content to help you with exactly what you’re worried about, often it can be like a firehouse throwing water at you at 100 miles an hour: “Oh, this article is great…and this one…oh and I should read that…omg!!!!”

How about an email that says “Start here. This is my most fundamental strategy. I’ll send you the next step in 2 days.”

That’s comforting. I will start there, and when you send another email in 2 days, I’ll probably open that too.

James Clear (who writes about a lot of stuff) did that when I joined his mailing list and it was great:

Add Value Technique #3: Send An Insider Tip That They Can’t Find Anywhere Else

Ever since the first caveman selling rocks wrote the word “Exclusive” next to his “Rocks for Sale” sign, people realized that customers love feeling special.

Here are the exact steps to take to send an awesome insider tip email and have your customers love you for it:

• I guarantee you know insider tips about your product that most people don’t know. List 10.
• Find the ones that are as specific to an action the user just took as possible. For example:
  “7 tips for fall fashion” is generic, common, and largely useless. I can go to the Yahoo homepage for that kind of hollow clickbait.
  “This is the best way to take care of the exact couch you bought. We own it and this is what we do.” is specific and pertinent.
• Just give those tips to them. Totally free.
• Then, and this is key, tell them it’s special. Tell them it’s an insider tip. Tell them they can’t find this anywhere else.

The last step is critical. You have to make it clear that you’re telling them a secret. Think about what happens when your friend says this, “Hey, so I don’t really tell people what I’m about to tell you…”

You perk up! It makes you feel special.

Companies can do this for free with their customers but they don’t. What a waste.

Here’s a great example of something close: free tips given to me by Odesk when I hired my first freelancer. Note what it was: exactly what I needed at that time. Note what it was not: “Congrats on your first hire! Here are 10 more freelancers you might want to hire!”

Add Value Technique #4: Send a (Truly) Exclusive Discount

Read this one carefully because most companies screw this up. This is a flavor of making your list feel special by giving them a discount but it’s not your typical product promotion email. It separates itself from that junk with 3 critical factors (and I mean critical):

• This cannot be the first email in your drip campaign. In fact ideally it shouldn’t be second or third either, but instead come later.
• The discount cannot be available to anyone not on the email list. It has to be exclusive.
• You have to tell them it’s not available to the public — that they are only getting it because they’re on this list.

An easy way to do this is to say: “Click this link, it’s the only way to get this discount. If you go to the site, you won’t see the discount because it’s not available to the public. It’s only available for people on this email list.”

I can’t emphasize this enough: The generic, store wide, sale advertisements will drive customers away, even customers that actually like your product.

In fact, here is the sad but true reason why I ended up unsubscribing from 20Jeans, even though their first few emails were great and I loved the product:

Sometime in March, I buy. I then get some good emails about taking care of my new fancy jeans. Then come a flurry of 20% off emails in April, one after another, which you see I never opened.

Then on April 15th, I unsubscribed. I couldn’t take it.

The sad part is that I actually love the jeans. Oh well. Back to Levi’s.

Here’s what you can do to make your discount more valuable and less spammy:

• Have the discount be related to some action the user just took, not store wide.
• Pair the discount with one of the three other value add emails above, so the entire email is not a promotion. For example, send me a case study, then at the bottom of the email, tell me there’s a related exclusive discount only available via this email.
• Have the subject line be about the advice or my purchase, not the discount. We’re all trained to ignore “75% off! Get it now!!” emails.

The Mechanics of Good Email Drip Campaigns

Now let’s talk about the mechanics of assembling these value adding nuggets into good autoresponder sequences.

Drip Campaign Tactic #1: Use Natural Language that Humans Speak, Not Marketing Nonsense

Email (especially the subject line) is one of the worst places to use marketing language because everyone’s favorite emails are from real humans who use real language. So we’ve been trained to like real language emails, not marketing emails.

For example, which of these two emails are you going to open:

Obviously you’re not going to beat the second email in the screenshot, but the aim is to get as close as possible.

Here are some signposts:

• If every sentence ends with an exclamation point, you’ve gone too far
• If you include special characters like stars or hearts in the subject line, you’ve gone too far
• If you’re talking about your company more than the recipient, you’ve gone too far
• If it’s from a real human “Jim” instead of a company “Acme Team”, that’s a good sign
• If the subject line sounds unexciting “How these 3 customers decorated their house with ____”, that’s a good sign.

People may balk at the last one, “What? You want me to make my subject line less exciting?!” But it’s true. People can smell marketing speak from a mile away.

You don’t have to take my word for it, Mailchimp studied over 200 million emails (yes, 200 million), and concluded this:

The best email subject lines are short, descriptive and provide the reader with a reason to explore your message further. Using splashy or cheesy phrases to try to stand out more often results in your email being ignored.

Drip Campaign Tactic #2: Use a cliff hanger to get them pumped for the next email

There’s a reason you can’t stop binge watching House of Cards. Every episode ends with a brilliant cliff hanger. “OMG. She’s behind this?! I knew it! Ok, just one more…”

Your emails aren’t as exciting, I promise, but they can be improved with cliff hangers.

Do this: Present a chunk of advice across a series of emails and tease the next email in your current one. That’s it.

It works best for niche products and bloggers with very targeted lists.

For example, Ramit Sethi does this brilliantly on many sublists of his. The email below is part of a sequence he uses for people interested in one of his flagship courses. After giving a bunch of useful info and a free lesson about the topic (finding your dream job), he puts a little cliff hanger in the P.S.

Do you think someone interested in finding their dream job will open their email tomorrow when he sends it? Yes.

This can be done by any company sending valuable information that their readers actually want, including e-commerce. For example, if you’re selling motorcycles and parts, there’s a never-ending stream of information that bike enthusiasts would love to know about. Tease the next email in your current email: “P.S. Look for an email in 2 days where I’ll show you how you can save $300 a year on maintenance by doing a few things yourself.”

You can do this with any subject where people love more information: interior design, raising children, fashion, weight loss, etc.

Drip Campaign Tactic #3: More text is okay if the text is valuable

Marketers near and far will gasp at this, but: experiment with having less photos and more text in your emails. Why? Scroll back to the screenshot of the two emails in my inbox: “25% off storewide” vs. “Wanna get drinks after work?”, which one will be jam packed with photos?

Yes, for some companies, photos are key. If I’m getting case studies of people pairing cool outfits from the shoes I just bought, I want to see the photos.

But the vast majority of the time, photos are just ways for marketing folks to send the same old ads via email, because they have no other creative ways of adding value.

This doesn’t mean using a wall of text, it means sending valuable emails (case studies, insider tips, useful instructions, etc.) in regular language from a real person. For a great example, check out how Neville Medhora made AppSumo a lot of money from turning generic marketing emails into stories that people loved.

Which takes me to…

Drip Campaign Tactic #4: Have the sender be an actual human

This is such an unbelievably easy way to build a better connection with your readers, it should be a no brainer:

Have the email be from a person.

The higher up in the org chart the better. I know big corporations have a million bureaucratic excuses for not doing this, but if you’re a startup or small business, this is an easy way for your subscribers to build a relationship with a person at your company.

For example, WPCurve is a Wordpress development company and their emails come from their founders, and are written like a human would write it:

Drip Campaign Tactic #5: Ask for replies to get feedback

I’m amazed at how many companies (not just big ones), seem to only get user feedback via surveys that come once every year.

The subject line might as well say this: “Our CMO asked us to figure out why we aren’t meeting our engagement targets, and gave us a $50 budget, so can you fill out this 5 page survey for a 0% chance of winning a $50 Amazon gift card?”

No thanks.

You’re sitting on an evergreen source of feedback: the email itself. If you send it from a real human and have it simply ask a question every once in a while and say “hit reply and let me know”, guess what happens? Some people hit reply and let you know.

“But, Devesh, we’d be inundated with emails!”

That’s no excuse.

First, you can have the emails go to specific reply addresses (not your personal address). Second, if you’re truly a huge company and would get thousands of replies, just ask for replies from a subset of your list.

Step by Step Guide to Building a Breakout Email Drip Campaign

Now I’m going to walk you through an exact step by step process you can use to implement the techniques in this article to build your first high value email drip campaign.

Literally all you have to do is follow this process step by step to create value adding drip campaigns your subscribers will love.

Step 1: Start with the Initial Sign Up Campaign

Complex businesses have many “triggers” to send drip campaigns (when someone buys, when someone signs up, when someone joins a webinar, etc.) but the highest ROI will come from making your initial drip campaign awesome.

By initial, I mean the first place where most subscribers sign up with you.

Here are examples for the 3 businesses we’ve discussed (If your situation is unique, mention it in the comments and I’ll try to help as best as I can):

1. e-Commerce – You can either find the most popular product or product category, and create a drip campaign for everyone that purchases that product, or if you are collecting emails before a purchase (via a blog sign up, account creation, etc.), consider making your breakout drip campaign for those subscribers. They have yet to buy, so the ROI on a good campaign could be huge.
2. Apps & SaaS – The vast majority of the time the best place to start will be your free trial or most common plan sign ups.
3. Blogs & Infoproducts – This is almost always sign ups to your main email list.

Step 2: Get in the head of your reader and list 10 ideas for valuable emails you would want

This step separates the great drip campaigns from the average ones. Using the categories I listed above, come up with 10 ideas of useful information you would want if you had just signed up for this list.

Not every idea has to be good! Just list them. If you can list more, list 20. It’s vital that you get in the head of your reader and come up with ideas of what they would want.

If you get this far and give up at this step, you’re resigning yourself to having a mediocre relationship with your customers or readers. That’s fine, then this post is not for you. If, instead, you want to be seen as the premier resource in your niche, and build a long term relationship with your customers, do this step.

To help give you ideas, in my bonus for this post I’ve listed 10 ideas for value adding emails that Evernote and Zappos could send. You can download the bonus here.

Step 3: Distill your list down to the top 4 and write your emails

Confer with your team, your friends, your spouse, or (best option) your best readers and figure out what the top 4 email ideas from Step 2 are.

Then write your email, keeping in mind the Mechanics section above.

If you’re struggling, here is an easy way to generate 4 from the ideas above in this post (but this is just an example, the exact order and content can vary for everyone):

• e-Commerce and SaaS: Start with some useful instructions, then a case study, then insider tip, then an exclusive discount (paired with an additional case study).
• Bloggers: Start with some great case studies in 2 emails, then any combination of insider tips or useful instructions, depending on your content.

“Where should I put my ask?“

My general rule is to give as much value as possible before making an ask. That said here are some ideas to start with:

• e-Commerce – Put it at the end of the last email, and possibly follow up with an additional “hard sell” email. If the last email is a case study with a (truly) exclusive discount in it, it should be well accepted.
• Apps and SaaS – Same as e-Commerce above. But you should also experiment with putting a short line at the bottom of earlier emails that says “You can upgrade to one of our paid plans and get x, y, benefits here.” For example, at the bottom of really good case studies. If your emails are good, some fraction of readers of each email will want to upgrade.
• Bloggers – This depends on the blog, but I’d hesitate trying to sell anything in your autoresponder. For most bloggers this isn’t an issue since sales happen infrequently through separate launch sequences.

Step 4: In your first email, simply ask for feedback

You picked your top 4 emails? Good. Now hold on. Before you send those out, the very first email they get (right after they opt-in or double opt-in) is different.

In this first email, simply ask the subscriber for some feedback. Ask them what they are looking for, struggling with, trying to change, or hoping you will deliver.

This is critical for 3 reasons:

1. You get your customer in the habit of taking action, which will help tremendously when it comes time to ask them for something (registering, buying, whatever).
2. You make it clear that you are all about them. While your competitors are bombarding them with ads and promotions, you’ll be sitting back, sipping a cocktail, and knowing you’re building a real relationship that will pay dividends for years to come.
3. This is crazy, I know, but: You may actually learn something about what your customers really want.

Here are some ideas to get you started (ask one at a time):

• e-Commerce – Ask them what they’re hoping to get out of the product. Have they bought products like this before? What feature are they most looking forward to? What made them choose this? How canyou best help them use it, learn it, or take care of it?
• Apps and SaaS – People sign up for apps when they have real problems that need solving. Ask them about those problems. What problem are you trying to solve? What have you tried in the past? What are you stuck on? What are you hoping to get out of this?
• Bloggers and Infoproducts: This is easy. Your blog or info product is on some topic, just ask them what they’re struggling with on that topic. You’ll get a great sense of what real problems your readers have (or think they have).

Step 5: Don’t stress over spacing, pick one and push go!

The only thing before pressing the start button is how to space out your emails.

This should be tested!

Pick a spacing that you think won’t be annoying but also frequent enough to keep you on their mind. I’d start with:

1. Immediately (Ask for feedback)
2. 1 days later
3. 2 days later
4. 3 days later
5. 3 days later

And adjust from there. Bloggers can generally get away with a tighter spacing while e-Commerce will come across as pushy more easily if you send too many emails at once. But you need to test it.

Remember, if you’re emails are good, and actually valuable to your readers, spacing becomes less of an issue. If I was going to buy a gadget, and I was really obsessed with it, and you were sending me really cool case studies and info about the gadget, I wouldn’t care if you sent those to me every day. But if you keep peppering me to buy more, I’m going to unsubscribe.

My Bonus For You: Make Your Own Awesome Email Drip Campaigns

To help you take action, I’ve made a special bonus for this post.

Click the download graphic below to get the following bonuses free:

1. A step by step checklist that distills this post to the essential steps – so you can get started ASAP and have a download or hard copy to refer to later.

2. My personal swipe file of 10 marketing emails in my inbox and notes on each one. This is a great reference for helping develop your emails.

3. A list of 10 email ideas that Evernote and Zappos could send – to help you come up with more ideas.

Click below to get these bonuses: