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

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:

  1. 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 ...).
  2. 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

Subject: Close & HubSpot | Follow Up Resources  Hi Steli, Thank you again for the discussion today, it was a pleasure speaking with you!   I am including a 2 minute video during which our co-founders describe how inbound marketing works – you can check also out our Cambridge office space, see here.   As we discussed, HubSpot offers an all-in-one marketing software platform that helps businesses of all sizes generate leads and convert them into customers. HubSpot has everything a modern marketer needs to do marketing right—all in one, easy-to-use product. HubSpot software includes SEO, blogging, social media, email, automated workflows, landing pages, lead intelligence and analytics tools to help marketers get the job done. You can see the full list of our products here.   HubSpot is an annual membership, which includes access to all of our software tools, 7 one-hour sessions with a dedicated consultant and continuing education and support all throughout the year. You can take a look at our pricing page here.   HubSpot customers experience an average 2.7x increase in traffic after 12 months of active use and lead database growth of 30.4x after 12 months of active use, see our ROI report here.   Please feel free to contact me with any questions. We look forward to helping your business grow as part of the HubSpot team!   All the best,

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

Subject: HubSpot & Close Hi Steli, Per my message today, I called to see how your internal decision making process  is going. More importantly, since we are going through a price change on 10/1, my manager, John Doe ( has authorized each rep on my team (2) 15% discounts on the cost of the software for customers who are able to sign up by 9/30. Not only would this lower the price of the software, but you will be grandfathered into the legacy pricing in the future. Today, Pro is slated to increase 2400/year. One of my coupons is spoken for, but I'd like to offer the other one to you. If this is of interest, please let me know as soon as possible. Thank you,

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

Subject: Should I Stay or Should I Go? Hi Steli, per my message today - I've tried to reach you a few times to go over suggestions on improving your  website, but haven't heard back from you and that tells me one of three things: 1) You're all set with inbound marketing and online lead generation, and if that's  the case please let me know so can I stop bothering you. 2) You're still interested but haven't had the time to get back to me yet. 3) You've fallen and can't get up and in that case please let me know and I'll call  911 for you… Please let me know which one it is because I'm starting to worry… Thanks in advance and I look forward to hearing back from you!

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

Subject: Thank You From Hubspot Steli, In reviewing some outstanding business today, I’ll be taking Close out of my  current follow ups at this time. Where we’d initially agreed in the value of our service to strengthen your online  engagement, I’ve reached out to you on several occasions following our initial  discussions. Having not received any replies to date, I assume that we’ve either  fallen off your radar or perhaps the interest has diminished to the degree that my  follow up is no longer warranted. I appreciate the opportunity to work with you and wish you the best with your  ongoing marketing efforts. I'd be happy to speak with you when you are ready to  invest resources into generating leads from your site. Best,

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:

  1. Hey, welcome, here’s some information. When can we talk?
  2. Hey, here’s some more information. Contact me!
  3. Hey, if you reply now you can get it cheaper.
  4. I’m really putting effort into helping you, and you’re not getting back. Contact me.
  5. 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

Subject: Important info on your first shipment Hi Steli, I’m Lizzie Walker, your Trunk Club stylist. I can’t wait to put together your first trunk  of great clothes. Before I do that, we need to have a quick chat on the phone, so  that I can get an idea of what clothes to send. Please respond to this email and let me know the following: - What's a good day / time to chat? - How did you hear about Trunk Club? Also, feel free to call me any time at the number below. Hope to hear from you soon!

Email #2

Subject: Steli — It's your stylist at Trunk Club Hey Steli, I recently reached out to you about the Trunk Club clothing service that you signed  up for. As you can tell, I’m really excited to help you get started with a trunk of  great new clothes. Let me know when you have 5 to 10 minutes to chat in the next  few days, and I’ll get a trunk to you right away. I’m happy to work around your schedule (mornings and evenings are completely  fine times to talk), and if you’d prefer to call me, you’ll find my number below. Thanks!

Email #3

Subject: Trunk Club — Still interested? Hi Steli, Just checking to see if you still want to move forward with the Trunk Club service  that you signed up for. If you’re ready for your first trunk, awesome! Let me know a  good time for us to wrap everything up with a really quick phone call. Trunk Club is all about convenience, and I’m happy to work around your busy  schedule. Looking forward to hearing from you!

Email #4

Subject: Goodbye from Trunk Club Hi Steli, I was really looking forward to putting together a trunk of great clothes for you, but  I haven’t heard a response to my calls and emails. That means this will be my last  email to you. If you change your mind and would like to give Trunk Club a try,  please let me know and I’ll have you looking great in no time. Best,

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.


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
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 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.