A couple months ago, I had a serious case of deja-vu.

After I emailed an entrepreneur to schedule an interview, she CCed her assistant to handle the dreaded ping-pong that inevitably comes with finding a time to chat. The assistant, Amy Ingram, emailed me within minutes and proposed a few times for the call.

As soon as I saw Amy’s name I knew I had seen it before. Puzzled why she sounded so familiar, I did a quick search for “Amy Ingram” in my inbox. Sure enough, this was not my first time working with Amy. In fact, I had several emails in my archive from Amy, but all associated with different founders and startup execs across the country.

Now I was really curious: How could several entrepreneurs with entirely different businesses share the same personal assistant?

It turns out, they don’t. Despite sounding freakishly human over email and even having a LinkedIn profile, Amy is not a personal assistant at all. She is artificial intelligence. The brainchild of a company called X.ai, Amy is a service that schedules meetings for you. After you share your calendar with Amy, all you have to do is CC her on any meeting invite and she handles the rest.

“I live and die by Amy,” said David Barrett, the founder of expense report startup Expensify. “Meeting scheduling is something that you dread. Amy is incredible because she takes this awful experience that you avoid and makes it incredibly easy.”

Dennis Mortensen, the founder of X.ai, came up with the idea for Amy because of his own frustrations scheduling meetings. A frugal entrepreneur who didn’t want to shell out the $50,000 or more a year to hire a personal assistant, Mortensen estimates that pre-Amy he scheduled upwards of 1,000 meetings a year. The average meeting takes eight emails to find a time that works for both parties, he says, and he was curious why there still wasn’t an affordable solution to such a common workplace time suck.

Mortensen said the all-too-frequent pain point made it relatively easy to get investor interest around the startup. At the beginning of this year he raised nearly $10 million in Series A funding to scale Amy. The potential market is also huge: Mortensen estimates that 10 billion formal meetings are scheduled annually in the U.S. alone.

“We schedule meetings. That is the end of my pitch,” said Mortensen. “It is very easy for people to understand. I am serving the exact people I am pitching to in investor meetings… There is not a venture capitalist on the east coast that is not using Amy.”
More than just a workplace hack, Amy represents a critical shift in the future of software, according to Mortensen. Rather than have software that helps you achieve certain tasks (think Taskrabbit or Doodle), he says we will see more and more services like Amy that will do the job in full without your involvement.

Mortensen puts Amy scheduling meetings for you in the same category as a driverless car taking you from place to place: You don’t really know how it works, but the job gets done and that’s all that really matters.

“I don’t’ want to set up the meeting. I don’t want to be assisted or empowered to do it, I want to not do it,” he said simply. “What matters is that you wanted to have a call with me today and that happened. How that happens is of less importance.”
Mortensen’s relentlessness to come up with a solution for the billions of meetings that are scheduled every year begs a simply question: Could his company be the end of the personal assistant?

Just like Uber is now waging a perceived war against the taxicab industry, you could imagine a future where X.ai is fending off personal assistant and secretary unions all over the place. Yet the founder doesn’t see it ever getting to that point. Acknowledging that his outlook could be overly optimistic, he thinks Amy isn’t a “job killer,” but could help personal assistants be more efficient with their time.

Jules Miller agrees. The co-founder of legal services startups Hire An Esquire and an Amy devotee, Miller says technology like Amy allows workers to really figure out how best to spend the work day.

“When technology can do a better job than a person on things like scheduling meetings and recruiting, the workforce will change,” she said. “I don’t think it’s taking away jobs, but it’s changing the type of jobs that people do.”

(Dennis Mortensen)

Indeed, Amy is already absurdly human in the way that she interacts via email. She can remember where you prefer to take lunch meetings as opposed to coffee meetings as well as how long you like phone meetings. Yet it’s clear Mortensen has some work to do on the backend before Ms. Ingram becomes a serious threat to every personal assistant out there.

After adopting Amy as my own assistant for a couple months, I noticed she still doesn’t understand certain social norms: She once emailed a friend of mine several times over the weekend. She sent another colleague multiple follow ups to schedule a meeting while she was out of office. Also, the waiting list for Amy is some 61 groups long indicating that Amy has some infrastructure improvements to do before scaling globally. (An X.ai rep wouldn’t disclose how many people are actually waiting to be rolled on to the platform.)

Mortensen doesn’t contend to be done with perfecting Amy’s algorithm. In fact, he is laser focused on working out all those kinks before trying to have Amy solve any other tasks. Although it seems like a natural extension for Amy to soon be able to make restaurant reservations or pick out your air travel, the founder says he will not stop down this narrow path until email ping pong for meetings is a thing of the past.

“We are going to keep hunting this one problem,” he said. “I want to be the company that once and for all resolves meeting scheduling. If I can schedule all 10 billion of those meetings, I am in very good shape.”