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Complete Guide to SaaS email follow-ups

by Max Al Farakh · May 30 2016

Email marketing in SaaS is a hard thing to figure out. What emails do you need to send? When and how often do you need to send them? What should the email subject say? How do you avoid getting into spam? How do you make people open and read the emails?

It’s been four years since we’ve added our first email follow-up to Jitbit SaaS Helpdesk. We’ve kept working on them ever since. In this guide, I want to share everything we know about SaaS email follow-ups. You will also find specific examples you can steal for your app right away.

Why do you need email follow-ups

The purpose of email follow-ups is to bring your free-trial users back into the app and engage them. If your users sign up for a trial and you don’t contact them until the end, you’re leaving money on the table.

Email follow-ups are a great tool for reminding trial users about your existence. People have to deal with a lot of distractions and can forget that they’ve signed up for your app. You need to send them emails throughout their trial to keep them engaged.

Third-party tools vs. in-house solution

There are two ways you can go about implementing your email follow-ups: using one of the many third-party marketing automation platforms or building an in-house solution.

When we were starting out, there were few decent third-party apps and our budget was pretty tight. So, we decided to make our own tool (having good developers on the team helped a lot). The in-house tool offered us the flexibility we needed to start experimenting. However, this approach has drawbacks:

It takes a lot of effort to set up your mail server to get a good delivery rate. If you decide to go with your server, your emails will often get into spam. We’ll talk more about that later.

It’s hard to manage. Every time I need to remember when we send a particular email, I need to jump into the code and figure it out. We don’t have a fancy centralized dashboard to see what’s going on. Also, we can’t make changes to emails quickly.

Adding any reliable analytics to your emails is complicated. You will probably need to use a third-party app, like Litmus, which is pricey. You can try to use Google Analytics to track open rates of your emails, but in my experience it is clumsy and unreliable.

You can’t A/B test the emails. A/B testing emails is a tricky thing to do. Many marketing automation platforms do offer working solutions, but there is probably no way you can implement A/B testing on your own.

However, in-house tools have one advantage. The ability to run complicated SQL queries to get the recipients you need is invaluable. Setting up behavioral follow-ups like “haven’t logged in for the last two days” or “didn’t invite coworkers” can take a lot of effort if you’re doing it with a third-party tool. So, if you want to nerd out with your queries, consider building your own tool.

If we were to start doing email follow-ups now, I would go for a third-party tool. Most of them cost around $50 to get started, which will pay off quickly.

Here are the marketing automation apps we like:

Drip was made specifically for SaaS email follow-ups. It’s easy to use. Its new “workflows” feature is fantastic and fun. If I weren’t stuck with our in-house tool, I would move to Drip instantly.

Intercom is a full-stack marketing automation platform. It offers live chat, a help desk and lots more, including email automation. Choose Intercom if you need a fully featured solution, not just email follow-ups.

MailChimp’s intended purpose is to run email campaigns, but nothing is stopping you from using it for follow-ups. I’ve included it because it is the only app of the three that offers A/B testing. Also, it may be cheaper because it has a free plan.

Avoid getting into spam

If you decide to go with your tool and have your SMTP server sending emails, you will face the spam problem. Spam will hurt your delivery rate – that’s one of the most important metrics you have. If you send emails and they are not getting delivered, what’s the point?

You can skip this if you’re going with a third-party app.

Basecamp has a great article on avoiding SPAM and increasing delivery rate: Giving away the secrets of 99.3% email delivery. Three things from that article helped us immensely:

  1. Setting up a valid SPF record is the most important thing you can do. SPF protocol has become a standard in fighting spam. It helps the receiving email server ensure that you – and not someone impersonating you – sent an email. So, if you’re going to send email from your domain, better set up an SPF record. You can Google a manual on how to do that for your hosting provider.

  2. Configuring reverse DNS goes hand-in-hand with SPF. SPF won’t work without configured reverse DNS. It is also needed to ensure that the sender is real, and that no one is impersonating you. Again, you’ll need to consult with your DNS provider on how to do that.

  3. Sign your emails with DKIM to increase your chances of getting into the inbox. It can be a bit complicated to implement. It’s optional, but you can look into this regardless.

Please refer to the article mentioned above for more information.

HTML email templates

You want your emails to look nice and pretty. Unfortunately, this is easier said than done. Email apps lag ten years behind web browsers for some reason. You still have to rely on tables and a bunch of dirty hacks for the layout.

I do not recommend doing it yourself. Fortunately, there are a lot of free ones you can use.

Campaign Monitor has 24 free HTML templates you can use, along with an excellent WYSIWYG builder. There is an option to download HTML when you finish.

I will also attach our template. It’s a simple single-column layout with an image header, a call-to-action button, and a footer. It’s about as simple as it gets, but it works for us.

It looks like this:

jitbit html email template

Download Jitbit’s HTML email template.

Best time to send emails

The guys from MailChimp wrote an excellent article on this topic: “Insights from MailChimp’s Send Time Optimization System.” Our data pretty much confirms their findings.

Do not send on weekends. No one reads their business emails on weekends. And when they get to work on Monday, your email will be buried in their inbox.

Avoid sending on Mondays. Due to the reason above, sending emails on Monday is not the best idea. People are busier than usual on Mondays.

Fridays are even worse. We see lower open rates on Fridays. MailChimp confirms: mailchimp send day of week

Send during the work day. The highest open rates, according to our research, happen around 10 AM. It drops significantly after 18 PM. Here is MailChimp’s data that confirms this: mailchimp send time of day

Your emails have the best chance of being opened and read if you send them during the work day mid-week.

How many emails should you send

You want to send as many emails as possible without being annoying. There is no magic number. The Jitbit trial lasts 21 days. We send six to eight follow-ups during that period – that’s one email every three days.

You can send more. I think that one email every two days is fine. I couldn’t find any research on this topic, so this is based on my personal experience.

You can keep adding follow-ups until you see your unsubscribe rate going up. I know that a lot of companies send one or more emails every day during the trial, but that is too much. The last thing you want is someone clicking “mark as spam” on one of your emails.

Email metrics you should track

Email analytics is not easy due to email apps security restrictions. There are three things you can track reliably and easy:

  1. Unsubscribe rate – how many people unsubscribe before the end of your follow-ups sequence. If this number goes up, send fewer emails or add more value to them.

  2. Open rate is a good indicator of how good your subject line and “from” name are. In other words, it shows how tempting it is to open and read your emails.

  3. Click-through rate shows how good your call-to-action and email content is in general.

Types of email follow-ups

There are many types of emails you can use. You want to try different things to figure out what works for your product.

Time-based. An email you send once users reach some time milestone in their trial. “Welcome to the first day of your trial,” “You’re halfway through,” and “You have three days left” all fall into this category.

Behavioural. You send these emails depending on what users do or don’t do during the trial. Think of them as tutorials on the features you think are important to use to get the most out of your product. More on that later.

Educational. Something about the problem you help solve with your product. For example, we sell a help desk app, and we send our users articles on how to do customer support better.

Transactional. Anything from a user credentials reminder to daily status updates from your app can be used to grow your conversions. In fact, this is the most under-utilised category. Here is a great article from Vero: The Complete Guide to Transactional Email

Personal. An email sent from an actual person. Its purpose is to start a direct conversation with a potential customer. We have a great example of this later in this guide.

Different types of follow-ups work better for different products and industries. It’s a good idea to give them all a try.

Key components of a great follow-up

All our follow-ups, except one, follow these guidelines:

Time-based follow-ups

The purpose of time-based follow-ups is to bring trial users back into your app and remind them of your existence. Here are all the time-based follow-ups we use.

Basic follow-up on the seventh day

From: Alex from Jitbit 
Subject: Jitbit Helpdesk follow-up

Hi, this is Alex from Jitbit Software.

About a week ago you signed-up for a free trial of Jitbit Helpdesk. You have another two weeks ahead of you since we offer 21-days trials.

1.  If I can be of any help - just let me know (simply by replying to this email).
2.  If you need more time to test our software - that's also no problem, we can extend your free subscription even beyond the 21-days.
3.  If you would like to convert your trial account into a full-featured subscription, please do so here

You can login into your app with a single click (no need for login and password): login


Best regards, Alex, founder of Jitbit

Three days before the trial ends

From: Alex from Jitbit
Subject: Jitbit Helpdesk trial is about to expire

Hi, this is Alex, the founder of Jitbit.

Just a reminder that your Jitbit Helpdesk trial expires in 3 days.

If you are ready to purchase, please use this link: buy now

IF YOU NEED MORE TIME, we'll be happy extend your trial. Simply drop us a note.

We are happy to help as you work through the remaining days of your evaluation, if you have any questions or if you need some more time with your trial, let us know by replying to this email.

You can log into your app with a single click (no need for login and password): login

Best regards, Alex, founder of Jitbit Software

The trial end

From: Alex from Jitbit
Subject: Your Jitbit Helpdesk trial has ended. Do you want a free extension?

Hi, this is Alex, the founder of Jitbit.

Your 21-day trial period has just ended. But don't worry - we're keeping your data for five months, in case you'll want to revisit our app in the future. Your help desk will also stay active for the next couple of days to give you some time to purchase it if you decide to do so.

If you didn't have enough time to test Jitbit, we could give you two more weeks for free. Just reply to this email and we'll get you sorted.

In case Jitbit didn't work for you, I'd love to hear your thoughts on how we can make the app better for you. If you have a minute, please reply to this email to share your thoughts and ideas. We'd appreciate it.

Best regards, Alex, founder of Jitbit Software

”Win back" follow-up 90 days after a trial has expired

From: Alex from Jitbit
Subject: Give Jitbit Helpdesk a second chance...


Hope you are doing fine!

A few months back you gave Jitbit Helpdesk a try but decided to leave for some reason. I thought I'd check in on you and see if you want to give it another try.

I'd like to offer you another free 21-day trial. We still have all your data, so you can pick up where you left off.

It is just one click away. If you're interested, click here to reactivate your Jitbit Helpdesk now.

You can also reply to this email if you have questions.

Alex, Jitbit founder

Behavioral follow-ups

Behavioral follow-ups are emails you send based on users’ activity. You can use them to nudge users to do an important thing they need to do to get the most out of your app and eventually convert into paying customers.

These are pretty specific to our help desk app, but I’m sharing them in full for your reference.

When a user hasn’t logged in for two days after the sign-up

From: Alex from Jitbit
Subject: We haven't seen you in a while...

Hi, this is Alex, the founder of Jitbit.

We've noticed that you haven't logged into your Jitbit Helpdesk account in a while, and we want to make sure you know how easy it is to get it set up. You have almost three weeks ahead of you since we offer 21-days trials, and we want to make sure that you will get the most out of it.

If I can be of any help - just let me know (simply by replying to this email). And if you are ready to convert your trial account into a full-featured subscription, please do so here: buy now

You can log into your app with a single click (no need for login and password): login

Best regards, Alex, founder of Jitbit Software  

Asking them to invite coworkers

From: Alex from Jitbit
Subject: Introduce the team to your new helpdesk

Hi, this is Alex, the founder of Jitbit.

I've noticed that it's been some time since you've signed up, but you still haven't added your team members to your Helpdesk. We've designed Helpdesk for teams, and it shines when you start to work together. Why not invite them now and let them get acquainted?

Just go to the admin panel – Users, companies and permissions and press the Add User button. Then create a user and choose "technician" role on the next screen. They will get an invite email with the URL, login, and a password.

I hope you will enjoy working in our app with your team. If you have any questions, just reply to this email

Best regards, Alex, founder of Jitbit Software

"Customize design" - to those who haven't

From: Alex from Jitbit
Subject: Customize your help desk looks

Hi, this is Alex, the founder of Jitbit.

I noticed that you left the default design in place. While it looks great, why not change it to make it look more like a part of your company website? You can change the colors and upload your logo in seconds. Give it a try on the top of the General Settings page in the admin panel.

If you have any developers at hand, you can go even further and make use of the Custom CSS setting. That makes your possibilities endless.

Best regards, Alex, founder of Jitbit Software

"Introducing automation rules" to those who hasn't tried

Automation Rules is a very powerful feature of our app, and we want to make sure users see it.

From: Alex from Jitbit
Subject: Cut your support routine with Automation Rules

Hi, this is Alex, the founder of Jitbit.

Welcome to the last week of your trial. Thanks for sticking around! I thought it would be a good time to dive into more advanced stuff.

You can trust our Automation Rules module to do the most boring parts of your job. Automation Rules are smart filters that let you take various actions on tickets depending on different conditions. It is a powerful tool, which will save hours for your team.

This is one of the most used and loved features among our current customers. Check out Automation Rules in the admin panel. I think you'll love it.

Best regards, Alex, founder of Jitbit Software

"Install widget on your website"

This is our newest follow-up. I wanted to experiment with having an image inside the email. My results are not final, but I’m pretty confident it increases CTR.

Hi, this is Alex, the founder of Jitbit.

Jitbit Helpdesk features a lightweight widget that you can install on your website. Make it easy for your visitors to contact you at any point and see your sales go up. The widget is customizable – you can change the colors, so it fits right in on your site.

Jitbit Helpdesk Widget

Check out Support Widget in the Admin panel.

Best regards, Alex, founder of Jitbit Software

Personal follow-up

Now, last but not least, the only personal follow-up we have. I have an entire article about it: “A single most effective SaaS email follow-up you’re probably not using yet.” I really recommend that you read it.

Here it is:

From: Max from Jitbit
Subject: One quick question...


I'm Max, a co-founder of Jitbit. Sorry for another email, but I really like contacting our users personally to get to know them better. I have just one quick question: 

Was everything clear during the sign up so far? Can we help with anything? 

If you have a minute to answer, that would be great. If you have any questions of your own, I'd be happy to answer.

P.S. Your reply to this message will go to our help desk so that you get answers to your questions faster. I do my best to reply to these tickets personally, but someone else from the team may also respond.   

Co-founder, Jitbit

We send this email 30 minutes after the trial sign-up. Note that it comes from me, Max, not from Alex. Unlike the other emails, this one is in plain text and looks like it was sent manually by a real person. All these things help differentiate this follow-up from the rest.

The purpose of this email is to start a conversation with potential customers. We were able to fix a bunch of things with our sign-up and onboarding process and engage a lot more users by answering their initial questions quickly.

This follow-up has a 15–20% response rate, which is crazy. I recommend that you steal it for your app.


Some extra resources on this topic I recommend that you read:

Just Good Copy – find more inspiration for your follow-ups

The 17 emails we send to engage customers, reduce churn & increase revenue from Baremetrics

Behavioral Emails That Keep Customers Coming Back (with Examples from My Inbox) from Unbounce

CAN-SPAM Act: A Compliance Guide for Business – because you don’t want to break the law

MailChimp Blog has a ton of information about email

Autoresponders are Dead: 5 Types of Follow-up Emails from Lincoln Murphy