Steal these high-converting sales email drip campaigns from 2 killer startups

There are a lot of great resources to learn about drip emails, but one of the best ways to see what’s working now is to study the email sequences of successful, fast-growing companies are sending to their leads now.
There are many different objectives you can achieve with drip campaigns, but these two case studies are focused on moving someone who signed up for a free trial or a free account forward in the sales process.
How do you get someone who signed up on your website to schedule a phone call with you, so you can qualify and sell them?
HubSpot's email drip campaign
Let’s first look at HubSpot, the recently IPO’d marketing automation juggernaut.
How do they move free trial signups to the next step of their sales process? It all starts with a wickedly effective sequence of emails. Here the emails I got from them once I signed up for a trial:
Email #1

The second paragraph was most interesting to me. I signed up for their trial, and someone from their company tells me he reviewed our site and has suggestions. This does two things:
- It makes me want to reciprocate, because he's put some effort into it (well, if I wouldn't know this to be an automated email ...).
- It makes me curious what his suggestions are.
It's also a plus that he suggests two specific times to get on a call, and mentions that it's just 5 minutes.
Email #2

This email is a bit longer than what's common for drip emails, but in this case that's a good thing. Many HubSpot customers are companies with 50+ employees, and these numbers can help them sell HubSpot within their own organization. It also hits the sweet spot of what most people who are considering HubSpot probably want to know about.
Email #3

If I'd have sincere buying interest, the prospect of saving thousands of dollars would be a strong motivator to get me to act now, it creates urgency.
Email #4

This email is already pretty good by itself, and it has just the right amount of humor to elicit a response, but what it really does is it sets the scene for the next email.
Email #5

Now this is a killer email. It's commonly referred to as a "breakup email", and we'll get into a bit more depth about what makes them work later in this article.
What’s the purpose of these five emails?
Think about this question before you read on. What are they trying to achieve with each and every of these emails?
The call to action is always the same: They want you to respond!
If this seems ridiculously obvious to you, congratulations—but you’d be surprised how many people try to cram too many different call to actions into their emails.
The purpose of every email is to get a response. HubSpot wants to keep the relationship going. They want to turn a silent trial user into an active prospect with whom they can build a relationship.
The basic structure and psychology of these emails:
- Hey, welcome, here’s some information. When can we talk?
- Hey, here’s some more information. Contact me!
- Hey, if you reply now you can get it cheaper.
- I’m really putting effort into helping you, and you’re not getting back. Contact me.
- Ok, that’s it, it’s over. You obviously don’t want me, so I’ll stop wasting both our time. Goodbye.
Out of these five emails, the last one is the most effective.
Now let’s look at a really big and successful company with a completely different audience.
TrunkClub's email drip campaign
TrunkClub is a very successful B2C online fashion company. They made so much money that Nordstrom acquired them in 2014, and they have great marketing.
Here are the emails they sent me after I signed up.
Email #1

Email #2

Email #3

Email #4

As you can clearly see, this email drip campaign has the same structure, and also ends with a breakup email.
The breakup email
Why is this last email so powerful in the sequence?
Because it utilizes the principle of loss aversion. Your trial signups (just like all other people) strongly prefer avoiding losses to acquiring gains. It’s a well-known principle in psychology; losing $100 will make you feel more miserable than winning $100 will make you happy.
By taking away the marketing automation software or our trunk of great clothes, they make us desire it more.
Bonus: 3 more drip email sequences to study
This writeup on writing effective drip email sequences by Bryan Harris from GrowthTools also offers some actionable advice and shares 3 actual drip campaigns, analyzing what makes them work and how you can apply this to write money-making sequences yourself.
Conclusion
Study these sequences for your own drip campaigns and utilize the principle of loss aversion if trial users don’t respond. Do it in your own way that best fits your target audience.
Focus on writing effective subject lines. Both HubSpot and TrunkClub could probably improve their open rates with stronger headlines.
Constantly measure the effectiveness of your open and response rates. This is very easy to do when you send emails from Close. We not only show you who opens individual emails at what time, but you can also quickly get a big picture overview of your overall open and response rates.
You’ll probably find that using the structure of these two email drip campaigns will help you schedule more calls, just like it does for HubSpot, TrunkClub, and many others.
Want more tips on how to send effective emails? Click below to get our email guide!
Further reading:
Sales emails: Convert more trial users with drip campaigns
Four simple principles of an effective SaaS trial email series: Get the frequency right, be personal, send emails in response to user-activity and include a clear and strong call to action in every email.
Expert webcast recording: Drive sales engagement with triggered emails (with Colin Neederkorn, CEO of Customer.io)
The full 1-hour recording of how to automate personal, well-timed emails to close more deals.
How to write subject lines that get your sales emails opened
Want to increase your open rates? Don't blindly follow the widespread advice you find online. Here's what really gets sales emails opened.
Send Drip email campaigns from Close
Want to easily send drip emails from within Close? Close's email sequences make it easy to set up personalized sales email sequences.
Integration: Capture and warm-up email leads with marketing automation software, Drip
GetDrip.com allows you to warm up your leads with a pre-written sequence of behavior-driven emails, and track how engaged they are through lead scoring and conversion tracking.