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How to Convert Trial Users to Paid via Email | Jacob Suckow

How to Convert Trial Users to Paid via Email | Jacob Suckow

Jacob is the founder of Email Empire and the host of The Great Escape Podcast. In this episode, Jacob shares his strategies around how to use email to convert trial users into paid, including: the principles behind the email sequence, how many and how often to send email, what to say, and how you can maintain a healthy list.

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How is SaaS email nurturing different?

At a high level, SaaS is really focused on retention and engagement.

A lot of products are going to be focused on how long it takes to get net-positive on a customer.

Often, even if you have a site library with articles, the amount of customers who look through this and read it is very low. So if you could tailor the content that is provided by email into serving their particular needs, then you can get better results.

Most users really only know about 10 to 15% of what they could be using and getting out of a tool, products need to use emails to help people get engaged and learn how to use the tool.

Why is email nurturing so important?

Ultimately, if you want to get someone to become a paid user, that’s the biggest hurdle. Focus on getting that one month paid.

After that conversion, retention is much easier than that initial conversion.

On the front end, for every paid user, general conversions tend to be very low. That’s the nature of the beast because there are so many tools out there and the biggest area of opportunity.

What should you focus on after trial signup?

  1. The first thing you want to focus on is getting engagement from the user.

In 14 to 30 days, many people are only hopping into the platform that you provide once or twice, it’s really hard to engage these users, so you really need to focus on getting that engagement first. Show them that there is a dedicated team of actual people who care and that they can talk to about using the tool.

This is also massive for shaping their perception of the brand long term. This helps them to understand that there are people behind the product and that what they say matters.

So in your first emails, find ways to ask them, what is the biggest problem that you’re working on that made you sign up?

This is a good way to engage them and build an understanding of your users.

For example, a sales OPS platform may find that users tell them that they’re looking for help with forecasting issues over a 12 to 18 months life cycle. But more specifically, the issue may be accuracy over the long-term deal flow. The users tell them that there is no way to relay historical data into future insights.

Now, if you didn’t ask your users what the main problem is that they’re looking to solve, they may not even be shown material that shows them that there is a feature to handle this, or, they may even be unaware of how to use it.

This is also why getting that manual response from your team is important.

  1. The next thing you wanna focus on is getting them to get a quick win.

You need to get them that quick win ASAP so that they can make that sticky association with your product. This will help them go beyond seeing your product as just another tool that they’ve signed up for.

Note, this isn’t about helping them save an hour or two per week. This isn’t about how they’re going to be using the tool 12 months from now, it’s about solving a specific use case that is the fastest win that you can get them.

What you will find is, for example, users who get set up with their account and build at least one dashboard convert at 20 to 30% to paid users. This is what you’re looking for.

How do you know what problems to focus on?

  1. First, you need to segment your audience into a couple of groups.

Very few SaaS tools are so locked down that they are in a tiny niche with no flexibility. Usually, they have a broad set of features, and some of those are much more valuable to certain groups than others.

Not based on features and benefits, but based on what problems they have.

  1. After you have identified what problems they have, you can then bridge the gap with the content that you have.

In this case, the content library is not simply an FA Q library, it becomes a tool for you to create a unique and different experience for each type of user.

Over time, you may find that there are four to even 6 segments, but the investment from your team is going to be very minimal over time to adapt those materials.

For example, let’s assume that you understand that there are three core problems that your product solves. Now, you can design sequences that focused on these three core problems. If people sign up you can now meet them with content that is relevant to them.

Which use case should you focus on first?

What you need to do is test each of them.

You will find that one or two out of the three starting segments that you have had better engagement than the others.

If you find a problem that isn’t interesting and engaging people in the first two to three weeks, drop it and move on.

Email marketing is a fast way to get data. If you have a few thousand subscribers, you have a massive database for getting data. But now it’s not just about conversion, but engagement.

Figure out what doesn’t land so you can focus more on what does.

How should you segment your list?

You really need to segment on just three things.

  1. How recently did they sign up?

  2. How frequently have they engaged with your content?

  3. How much have they spent on your product so far?

You don’t need to start with super strong segmentation, you just need a strong strategy to engage people for feedback so that you can adapt your system along the way.

If you only start your email campaigns based on targeting one person in mind, that’s also fine. You will hear from people who you are missing out on if you’re always collecting feedback from your list.

Over segmentation is a real problem for a lot of people. It is better to have less segmentation rather than too much.

So focus on three to five segments max, anything more and it’s not productive.

How do you get better feedback from your list?

You need to be asking specific questions.

For example, during onboarding, ask them first what do they want to see? What’s going to make their trial period really useful?

Pin the questions at the bottom of your emails. And make the initial emails about these questions. It’s how almost all my own boarding sequences start.

You’re going to have some people who are willing to speak up, and those who are not and hide their questions. You need to use the ones that are speaking up to fill in the gaps.

If only 10% of people answer, over a few thousand people that’s a lot of great qualitative data. It’s about getting that feedback at all.

How long should you discuss each use case?

The overall focus of your onboarding sequence use case information will depend on how in-depth usage is really required to solve the problem.

For example, if your product has a very high learning curve, and your free trial is only 14 days, and people miss just a few of them, then that’s OK.

You don’t have to use all 14 days to force them to learn how to use everything. You can do that over time with your long-term nurturing campaigns.

If that simply setting up their account and adding some integrations, for example, then that’s all we need to focus on.

How frequently should you email?

The answer is totally dependent on your audience.

The best way is to ask your customers in your audience who are already paying and get their feedback.

Ask them, would it have been useful to get an email every day for a week that shows you how to solve this particular problem?

Does emailing frequently tire out your list?

Training people not to open your emails by sending too many is one of the most common reservations I hear.

But to those people I ask, how often do you read things that you really enjoy? For example, if you read the news, you probably read it every day. Then, how often do you check your email? Probably every day.

Imagine you check every day, then you’re probably getting 30 to 40% open rates based on your audience. Which means, if you’re not sending every day then you’re missing 30 to 70% of your audience every day that you are not sending.

Mailing more often is the only way that you’re going to get in front of your audience as much as possible. If you’re only doing an email once a week, then the two to three emails in a month-long owned voting sequence you will likely only have talked to a third of your customers given a 30 to 40% open rate. E line in that situation, who are you really helping?

If you’re really worried, you can give them the option to reduce the frequency of your emails.

How do you start?

Start mailing every day, and request feedback on all your emails. You’ll see in two weeks.

For example, if you send out 100 emails, and 67 people tell you they only want it once a week, then you have the data to really know.

On the other hand, if you email every day, and only five to 10 people opt out of 100, then it’s going to be a net benefit compared to the cost.

People are much less judgmental than we think. And the fact that you’re engaging with your audience, is a big draw to your overall attention because people can see that there is someone behind the product who is listening to them.

Keep in mind that you don’t have to create a perfect experience, you just need to let it evolve and change based on feedback and the data.

Ben: I hope you found this interview as I did, I was quite happy to have discovered a tangible framework to implement, and I can say that I have actually scheduled consultations with Jacob myself and have seen results from his work.

Having worked with Jacob, some of the easiest wins to implement right away is to make that first one or two welcome emails for anyone opting into a product or list that asks them about what they are interested in learning. Then you can start to build up your email chain based on Jacobs’s bias above, about constantly iterating on their interests in solving problems.