Five minutes with: Henn Ruukel, Fleep

​Enterprise messenger platforms have taken the business world by storm in recent years. CEO Henn Ruukel speaks to GrowthBusiness about running Fleep, a business messenger platform built by members of the team behind Skype

​Enterprise messenger platforms have taken the business world by storm in recent years. CEO Henn Ruukel speaks to GrowthBusiness about running Fleep, a business messenger platform built by members of the team behind Skype

Henn Ruukel, CEO of Fleep, traces the business messenger platform’s early history and rapid growth across Europe. 

How did the idea come about?

As quite often happens, Fleep was founded out of frustration. While working at Skype for seven years we used Skype messenger for our work communications; although it had several flaws we learned to live with them until one day I thought, “Why don’t I just leave Skype and build a better messenger for work communications?” So to begin with, it was mainly just about fixing Skype’s flaws, including:

  • Offline messaging – Skype sent messages directly between users devices, thus in order to receive messages you had to be online at the same time as the sender. Skype has partially improved this now, but not fully.

  • Multi device support – Skype messenger doesn’t work that well if you sign in from multiple devices at the same time, like your phone and computer for example, or multiple computers.

  • File sharing – Skype messenger supports “sending files” which requires all parties to be online at the same time but it doesn’t support sharing where you can post a file to a group conversation and it would then be available to all members of the group at anytime and from any device.

When we sat down with the founders of Fleep and started discussing these issues, we understood that while fixing Skype’s flaws is a nice idea, there is actually a much bigger problem to solve called “email.” Despite different messengers having been on the market for years, we still need to fall back to email in order to work across organisations and teams.

That’s how we got to the fundamental concept of Fleep, which is a modern messenger with a twist, as it works with email. Using Fleep, you can include email participants within your conversation, who will receive all messages and files as normal email threads, including their replies which will also flow back to Fleep. The simple approach allows Fleep users to have conversations with anyone who has their email address, without the need to convince them to become Fleep users first. We think this smooth transition path allows people to leave email behind and use Fleep for all work communications, both with their team and with anyone else.

What differentiates Fleep from competitors like Slack? 

Slack is an awesome product for tech teams who need to communicate internally, but it is a closed system and does not solve the issue of cross-organisational use. Fleep’s main difference is that it is open – our users can have conversations with any other Fleep users or with anyone that is using email. So if you are working in a team of ten people, then in Slack your maximum reach is nine people, and this would be the same even if Slack had 200 million users. In Fleep, you have the ability to reach billions of people immediately via email, in addition to Fleep’s fast growing user base. Slack’s growth has been enormous – they have been growing by replacing internal email for many organisations, but their model doesn’t help users with their team’s external email – Fleep does both. Thus I think we are quite different and there is plenty of room for both of us; yet while we are both eating email, we are both still tiny in comparison to email.

Who were the early adopters and how did they respond to migrating away from email?


Fleep’s early adopters have been teams and individuals who need to work across organisational borders to get their work done. We see many tech start-ups using the service, but we also have large construction companies and FinTech companies using Fleep. What we have learned is that migrating away from email is rarely a goal in itself; rather we see Fleep allowing them to transition their communications away from email smoothly, at their own pace, and parallel use of Fleep and email might last for months. It is not about technology but about habits and culture. Our users have said it takes time to get used to new messaging culture, for example to stop habits of writing lengthy emails with long intros and thank yous and instead write short messages that are straight to the point, even if other parties are participating via email. Once they make this cultural shift towards drafting short, to-the- point messages due to Fleep’s conversation-centric nature, it helps them to save a lot of time (and also saves time for their colleagues).

Praseeda Nair

Praseeda Nair

Praseeda was Editor for from 2016 to 2018.

Related Topics