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A day in the life interview with Henn Ruukel, Co-Founder & CEO of Fleep

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Next up we spoke to Henn Ruukel, Co-founder and CEO of Fleep, a messaging app which is email compatible and promises to simplify communication. The idea came to Henn while he was at Skype, and Fleep has everything Skype was lacking, plus more…


1. First can you tell us a bit about your job? What does your company do?

I’m Co-founder and CEO of Fleep – a messenger for project teams. As usual early-stage CEO job mine is to take care of everything no one else in the team does 🙂 I think my main role in the team is being Product Owner – owning the product vision and strategy, prioritizing product development and leading growth activities. In addition to that, my time is split between many activities from representing Fleep in public to hiring, financials and investor relations.


2. What brought you to this area?

I’ve kind of been in the area of business communication my whole career (omg 20 years already). I started in telecoms, moved over to Skype and one day, after 7 years in Skype I had the to idea to leave Skype and build new messenger for businesses. It triggered from the mediocre experience with Skype messenger which we used for communication in Skype, but when we came together with founders and started drafting the Fleep concept we understood quickly that fixing Skype flaws is not enough, we should aim for building messenger that could replace email conversations for business people. That’s how we started with Fleep in the end of 2012 and we have stayed true to our vision.


3. What time does your day start, and what does your typical work day schedule look like?

6:40 is default alarm time. Although we don’t have strong culture of working from the office and many in the team prefer to work from home, I personally like to work from the office. Schedule depends on a weekday, regular team meetings (sprint plannings, groomings, design reviews etc.) fill most of my Mondays and Wednesdays, on other days there’s more space in between scheduled meetings which leaves me room to actually get something done, usually related to preparing specs for upcoming developments or growth analysis. We don’t have strict rules but as the company grows I’m keen to set rule where max 50% of workday can be filled with meetings per person. It’s easy to get overwhelmed with meetings and feel busy although meetings should be only used to exchange information and agree on next steps – thus actual work has to happen in-between meetings. Also we have strong messenger culture in Fleep – we save a lot of meetings time thanks to Fleep messenger where many small issues and questions are solved on the fly.


4. What kind of projects are you currently working on?

We rolled out new Teams feature into Fleep in July, from there onwards our focus has been on improving new teams onboarding experience. Fleep is awesome product for teams who have settled in. Now we want to make it easier for new users to onboard their teams into Fleep, as teams and users are coming with different background and expectations it is a complicated task consisting of iterating on onboarding experience, learning from users feedback and metrics, I think it will take at least whole September before we start building new features in the pipeline.


5. What do you consider the greatest achievement in your work to date?

I think it’s hard to call out any specific achievements, firstly as there are very few things I’d consider being my own achievements, rather most what we achieve we achieve as a team. If anything then maybe getting started with Fleep – finding co-founders and initial funding, but from there onwards it’s always been team effort and I’m proud to be part of that team and proud of the awesome product we’ve built 🙂


6. What is the one app you could not live without?

As I forwarded all my emails to Fleep 1,5 years ago and as my role mainly consists of communicating internally within the team chats and with people outside (from Fleep to email) then I’m heavily dependent on Fleep messenger app. I haven’t done any stats but I think it takes most of my screen time on my MacBook and on my iPhone 🙂


7. What’s the best thing about working at Fleep?

Feeling that you are doing something useful that thousands of people use every day in their work and which makes their workday easier. Also I enjoy early days where team is still small and nimble, feeling of being able to change things I guess.


8. Where is the after work hangout?

As I like outdoor sports and as my youngest daughter is only 1,5 years old then it’s either in the cycling / running in the woods or at home with my kids 🙂


9. Who is your professional role model?

Probably closest match is Steve Jobs – I like his approach being product centric but as much I’ve read about him I don’t share his style of managing / co-working with people.


10. What makes Tallinn a good city for startups?

Legal environment is very simple, you can start a company within 30 minutes from your computer. Infrastructure (internet access, office space, accommodation, food) good and relatively cheap. Good talent available and people are trustworthy and loyal.


11. What are the top 3 qualities you look for in an employee?

I usually hire for attitude rather than skills, and I’m looking for people who:
Like to solve problems rather than create new ones
Like to work with other people and understand that together can be achieved more than alone
Like to learn new things, are open for tasks and roles they haven’t done before


12. And finally, what is the one piece of advice you would give to an entrepreneur starting out?

If you have idea you believe in, have at least one potential user, one co-founder and one potential investor – get started you’ll learn on the way. Although you asked for one piece of advice my other advice would be – stay true (to yourself, team, investors, users.)


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