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CEO & Founder, Dennis Mortensen, Tells Us How is Meeting the Demands of the Remote Work Revolution

kokou adzo



Dennis Mortensen

First of all, how are you and your family doing in these COVID-19 times? 

Dennis Mortensen: The family is happy, healthy and in good form, which is a blessing. Now, we are also very fortunate to have room for a dedicated office, which I can highly recommend, should that be a luxury available to you. A dog, two cats, two daughters and a loving wife does add a little commotion if you just work out of the kitchen 🙂

Tell us about you, your career, how you founded

Dennis Mortensen: I’ve been an entrepreneur my whole working life and the connective thread through it all has been data. Finding ways to extract meaning from the seemingly unstructured stream of information-pushed towards us at all times. Our prior startup did Enterprise Web Analytics and got acquired by Yahoo! Our last startup did Predictive Analytics and got acquired by Outbrain. Our current startup,, is rooted in AI, but let me rewind and tell you how it got started.

On July 1, 2013, I bought the URL at an auction. Expensive. Ouch. Then in October of that year, I continued my conversations with my co-founder Marcos about killing the inbox, which led to the conclusion that meeting scheduling accounts for much of the bloat. We brought the band back together to hack away at a machine-driven solution for meeting scheduling. Mostly, me and Marcos fooling around on the virtual whiteboard, trying to understand whether the meeting-scheduling universe is a bounded space. We also discovered that the purchase of a single yogurt buys four undisturbed hours at the Union Square Pret a Manger (pre-COVID times). Over the next few months, we expanded our scheduling experiments and tests. In all, 45 friends accepted the offer to use the early beta of the scheduling tool. On April 14, 2014, was incorporated, and the rest is history!  

How does innovate? 

Dennis Mortensen: is the only scheduling solution that gives you a Scheduling AI to request meetings over email and Slack (for free!). This innovative approach does not come cheap. For the first four years of our existence, we invested massive amounts of time at considerable cost into assembling what might be the largest meeting scheduling dataset in the world. We then trained sophisticated AI models that can understand and process complex scheduling requests. The result is elegantly easy-to-use, which should be the goal of any good piece of technology.

As for how we continue to innovate: We are obsessed with our customers. Many companies will tell you this, but we live it. I spend most of my days speaking to our customers and prospective customers, as does much of the team. There is no substitute for talking to your customers, hearing their pain points and wish lists, to inspire creative solutions.

How has the coronavirus pandemic affected your business and how are you coping?

Dennis Mortensen: Like many virtual meeting solutions, we saw strong growth in signups and meetings scheduled around the time that most of the world started working remotely. What’s really encouraging is that this growth has continued, exponentially. Scheduling software is becoming a must-have for individuals, small teams, and enterprise companies.’s solution is fully operational out of the box, and it’s also easily customizable to effectively automate any existing manual scheduling processes.

As for our team, we like to think we got a head start on figuring all this out since we went fully remote back in 2019. We put a lot of work into the transition, and I can truly say that it’s been a serious positive for the company. (We wrote up some of the lessons we learned here.​ )  

How do you deal with stress and anxiety, how do you project yourself and in the future? 

Dennis Mortensen: I am full of empathy for those founders and teammates who deal with stress and anxiety, and I see where they are coming from. I have always looked at the startup game, as just that, a game. The best analogy I can come up with is professional sports, where you surely play to win, but accept that you will probably lose a game here and there, and early in your career, more often than not. That’s just how it works, and you continue to play, because of your love for the game, and not for the idea of trophies.

Trophies are just nifty outcomes, but they are not what define the reasons to get up in the morning. Joy, excitement, and love are reasons to get up in the morning. In other words, your life’s worth is not attached to the success of the company, and you do the startup because you enjoy the journey. If you ever want to test this hypothesis, make some kids because they will love you unconditionally, and there is no customer churned, and no investor lost that can ever change that.

These are beautiful ideas, and if you are somehow able to adopt this mindset — it’s just a game — you’ll be awesome on all fronts. The best salespeople, the most confident ones, are OK with you not signing the deal today. We’ll sign it another day, and that alone, ironically shortens your funnel.

What’s something you’re especially proud of launching this year?

Dennis Mortensen: It’s hard to choose just one! Our team pushed 117 updates and feature extensions in the first 10.5 months of 2020, which is impressive for any company, but it’s especially bonkers when you remember we’re a rather scrappy team of engineers, data scientists, and growth hackers only. has scheduled meetings for people in 210 countries in 2020 alone. We continue to see strong signals that the demand is there for a truly global scheduling tool. We’ve been on a journey to full localization this year, adding many personalization options throughout the product, and I’m especially proud of our recent update ( that lets you request a meeting over email or Slack in any language.

Who are your competitors? And how do you plan to stay in the game? 

Dennis Mortensen: We consider our competition to be companies like Calendly, which solve a very narrow scheduling need, to the platforms like Google, Microsoft, and Apple themselves. is a tool for every organization to schedule any meeting, and we’ve worked hard to ensure we can meet every use case and automate as many manual processes attached to scheduling as possible.

Just like when we moved all our files to the cloud (e.g. Dropbox), and just like when we all started to sign our contracts digitally (e.g. DocuSign), it seems equally inevitable that we will all use software to help schedule our meetings in the not too distant future. As that happens, a new market for ~90 million knowledge workers in the US alone opens up. That in and of itself is interesting, but one of the more exciting things for us (and our current investors) is the natural network effects. gets better simply by more people using it.

Your website?

x​ .ai 

Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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