11 May 2016

The Best Ways To Engage Your SaaS Free Trials

The Best Ways To Engage Your SaaS Free Trials

After my previous post on user activation in SaaS, this could be considered the 2nd part of it.

Once, you know what you want your users to achieve, you can communicate and push them towards that goal through various means.

In this post we will explore the best ways to engage your new free trials for your SaaS.


I’d rank webinars among the top 2 ways of engaging your free trials. They are very engaging by nature, cheap and easy to deploy, they provide trust and convert.

I have expanded in a previous post on how to get started with webinars for your SaaS.

In order for webinars to make sense for you though (cost-benefit wise), you must meet the follow requirements:

  • Minimum 500 free trials per month | 60 webinars registrants for SaaS doing demo and not free trials based on a comment from Trevor Hatfield. For more info on SaaS doing demos, check the discussion here.
    Reason: if less, the volume of webinar attendees will probably be very low.
  • Lack of intuitive onboarding (or complex / mature product)
    Reason: if your onboarding is killer, you might want to push them go through it.

Notice that webinars, work for both self-served / low touch B2B SaaS and enterprise ones. I will expand on the differences between these 2 kinds of SaaS in a future post.


Onboarding is the UI/UX of your SaaS when someone signs up, guiding them to take specific actions and try your product’s features.

Onboarding is especially difficult for mature or complex products, because they provide so much functionality, that it’s not easy to explain it in such a short time and solely via UI/UX and small annotations.

However, it’s a must have and at the very minimum you should guide your new users to try the most important feature and taking at least 1 action. In the previous post on user activation I described a specific example.

Some SaaS with great onboarding experiences are Sniply, Buffer, ActiveCampaign, Optimizely and more.

Email Marketing

Specifically *drip email* is an email sequence that is sent after someone signs up.

The first level is a generic sequence that is sent to everyone regardless of what they do. Although, I am not a big fan of it and I am skeptical of its results, I’d say it’s good to have it because of the low cost to create and medium potential results.

The best drip email campaigns are by using tools like Intercom to send specific emails based on the actions each user has taken!

For example, if a new user is active using your SaaS, but she hasn’t tried out a really important feature after 10 days, you can send her an email automatically and let her know about it.

For this specific email functionality I’d first check Intercom, not only because of its functionality, but also because for some reason their emails tend to be delivered in the “Primary” inbox and not in the “Promotional” one.

This can be pretty big…

As always, test and research for your own specific situation and business, because no two SaaS are the same.

Live Chat

Live chat is rarely offered by SaaS, yet it’s greatly valued by users.

Usually, when a user signs up for the first time for your SaaS he wants to dig around and explore it. But, when he tries to find a specific feature or needs some help, being there with an active chat to support him in a fast way can be a game changer…

Of course in many cases you won’t be able to support it for all your new sign ups or free trials, due to sheer volume. However, you could test it out a couple of hours per day during office hours or only to your free trials with the highest potential.

Then evaluate if this extra cost in time and/or money makes sense for the ROI it brings.

Personally, live chat has played a major role for me to convert to various SaaS companies.

Customer Success

The holy grail of SaaS and retention. Lately there has been a lot of hype around it, but for good reason. Customer success can *really* move the needle, but in all directions, not just retention. This is for another post though.

In this post, it’s about engaging your free trials in order to make them successful using your product. Sometimes your product might not be the best fit for them and that’s ok. Lincoln Murphy has said it before me: “Help your customers achieve their desired outcome”.

I am sure you are thinking “hmm providing customer success for all our free trials or even customers is pretty expensive” and you are right. So, as always, let’s get practical; here is how to make it work:

You have to make your free trials know that you are there for them, in an automatic, yet personal and scalable way. This can be done via emails, or other means of communication, but that’s not the point. The *key* here is the content of the email and how you serve it.

Unbounce is a great example of what I am saying. Here is the first email they send you once you sign up:

unbounce welcome email 1
Notice how they get personal and send you all the options to get support

Now, you can also set your customer success manager to reach out to users based on KPIs like activity, size, company etc and give your users active feedback on what they have or haven’t done up until now.

For example, I remember when we first signed up for Unbounce and created a landing page or two, their customer success manager reached out to us with some specific feedback on the landing pages we had created and asked us if we wanted any help or if we had any troubles. Now, *that* went a long way.

How can you apply this to your B2B SaaS?


To wrap it up, it’s very important both how you reach your free trial users (so that they see your message) and what you say to them (so that they know you are there for them and how to reach you).

Of course, you don’t have to do only one of the above, but you can and should do a mix of those tactics, especially as you grow. You can start with the email which is the easiest to implement and then expand to webinars, live chat, etc.

As Jason Lemkin says in one of his articles, every 2nd time CEO started with 2 customer success managers, so I suggest you get at least one as soon as possible.

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