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Dennis Mortensen is founder of automated scheduling tool X.aiMalene Korsgaard Lauritsen

I was a little put off by Andrew Ingram at first, to be honest. I was trying to set up an interview with Dennis Mortensen, founder of automated scheduling tool, and Andrew, his assistant, kept coming back to me with inopportune times.

His first suggestion was late in the day and when I told him that didn't work, he offered another appointment a few days later. We went back and forth and I got the sense he didn't understand that I was on a tight deadline.

We finally ironed it out and I got to speak with Mr. Mortensen in time for this article. It was only then that I learned the truth about Andrew – that he is actually a machine, otherwise known as's main product.

I should have known, especially with Andrew's initials – A.I. – being a dead giveaway, in hindsight of course. But aside from the possible insensitivity toward my deadline, "he" seemed real enough.

"We've reached the point where it's hard to distinguish between what is a machine agent and what is a human," Mr. Mortensen says. "At some point it won't matter. What matters is you wanted to speak to us on the phone." is one of a number of startups aiming to simplify meeting scheduling by automating the process. Such tools use a basic form of artificial intelligence to match up participants' calendars, with details then relayed to each person via natural language processing.

New York-based has been working on its software since 2013 and is currently in beta testing, with a full launch planned for the fall. The company, which has 65 employees and has raised $35-million (U.S.) in funding so far, plans to charge enterprises a subscription fee to use Andrew and Amy – its other, "female" AI scheduler – on a monthly basis.

Mr. Mortensen believes there's a huge market in providing virtual assistants to companies – especially smaller ones that can't afford human versions. He estimates there are 10 billion formal meetings in the United States alone each year.

When a company signs up with, employees who want to set up a meeting copy Andrew or Amy in their e-mail and the AI takes it from there. The assistant does the grunt work of going back and forth to nail down a time that works for everyone.

Mr. Mortensen, a serial entrepreneur who has founded such companies as predictive-analytics provider Visual Revenue and digital agency Canvas Interactive, says the idea for came to him after years of setting up his own meetings. He figured he took part in more than 1,000 meetings in just one year.

"It just seemed like such a massive amount of pain where there could be an opening, where having an assistant isn't just a luxury for the few," he says.

Roy Pereira experienced similar frustrations, which led him to found The Toronto-based startup, which launched in February, is working on a similar scheduling assistant, but one that can also communicate via a messaging chatbot and SMS text, as well as e-mail. also wants to be able to book flights and even Uber trips.

The company currently consists of five employees and will soon be going after its first round of financing, Mr. Pereira says. Like, the plan is to charge monthly subscriptions based on the number of users a business has.

One challenge the startups are facing is convincing companies to trust them with their data. In both cases, enterprises have to grant the AI assistants access to their employees' calendars.

Mr. Pereira, who previously worked as the vice-president of marketing and product management at security firm Certicom before it was acquired by BlackBerry in 2009, says this is one of his primary concerns. doesn't sell user data or retain user names and passwords and is working on offering customers to store their other information in the United States or Canada based on their preferences.

"Obviously, because we're analyzing so much data, we have to be more sensitive," he says.

Mr. Mortensen says the system discards e-mail attachments as an extra privacy measure. Participants in e-mail chains can still see the attachments, but the AI assistant automatically discards them from its own inbox when they're received.

Experts say people have got used to using shared services that reside in the cloud, such as Dropbox and Google Calendar. Combined with continual improvements in AI, machine learning and natural language processing, that could mean a bright future for artificial assistants.

"People are more receptive to using this kind of technology," says Sheila McIlraith, a computer science professor at the University of Toronto. "There's a comfort level in dealing with bots and having faith that they can surrender that information or task to a bot."

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