The Magic Of AI -- And Amy Ingram

This post was previously published in an earlier edition of AI Insider.

Here’s  a confession: I’m not great at managing my calendar. Many years with a world-class executive assistant spoiled me into a false sense of security that my calendar will always somehow work out — magically. 

Not surprisingly, the magic has failed me on a number of occasions in my post-assistant life, to which several business connections can personally attest.  I often find myself wishing for someone to tend the tedious task of scheduling meetings, who can stop me from double-booking myself.  

I first met Amy Ingram through an email she sent to arrange a meeting with the CEO of a New York AI company.  Amy politely asked for my availability and offered three different time slots. I was slow to respond, and she gave me a nudge a few days later. I offered a different day. She came up with an option that fit my schedule, and sent out the meeting invitation with coordinates.  

My exchanges with her were peppered with phrases like “I’m sorry,” “Have a nice weekend,” “Thank you.” I had no idea Amy Ingram was a bot.

I began to suspect something was up a few weeks later when Amy reached out again – this time, on behalf of a business colleague who wanted to meet for drinks while visiting Boston.

He gave me the lowdown when we met: “It’s great. Once I’ve agreed to meet with someone, Amy takes over. She knows if I say ‘drinks’ or ‘breakfast’ that I mean a specific time of day. She knows my favorite places to meet, but if I’m traveling, she asks the people I’m meeting with for their suggestions. I don’t even have to get involved. And it’s only $40 a month!”

When you own a start-up agency, every hire matters. Holding off on a real assistant and using Amy instead can mean having the extra bucks to hire someone to help deliver a stronger product.

Amy Ingram was enabling this business owner to be scrappy and resourceful, practicing an even leaner “lean start-up” mentality.

The third time I encountered Amy,  I knew the score. I eschewed the niceties in communicating with her -- which was freeing. Amy booked an appointment that fit with her boss’ schedule and the availability I offered.

But (and here’s the kicker) I double-booked myself, which meant when the Amy-arranged appointment arrived, I had to ask my contact to come back in an hour, a mortifying mistake on my part!

Still more mortifying? The bot was doing a better calendar management job than I. It was time for action.

I contacted Amy Ingram’s company,, for my two-week free trial, but ended up committing to use her for at least six months. It takes time to adjust, and I don’t expect the experience to be perfect, especially in the beginning.  

In fact, one of the first meetings that I used Amy to schedule was meant to be at a friend’s office in New York -- but Amy booked a conference call (which was one of my defaults).

My friend and I had a giggle about that. It wasn’t Amy’s mistake as much as it was my own. I should have specified the meeting was meant to be in-person and indicated where.

I was able to correct the mistake by emailing this message: “Amy, this is an in-person meeting at my contact’s office. Please use the address from her previous email.” Done! No assistant could have made the change faster, including notifying both parties.  

Amy’s responses are automated, so they are similar to receiving an OOO message.  And note that I instructed her using natural language; I did not have to waste time fiddling with a technical platform. If I use language she doesn’t understand, Amy is quick to inform me. Amy will improve as I train her, but I will also improve over time, as I understand her capabilities and how to instruct her.  

I set up a call with CEO and Founder Dennis Mortensen to learn more about his company, which officially launched just two months ago. Naturally, I used Amy Ingram and he used Andrew Ingram (her brother) to do the scheduling, which demonstrated the speed of bots versus humans: our meeting time was set in a matter of seconds.  

“Imagine how much time can be saved when teams and companies use this product,” Mortensen professed. He estimates that in the U.S. alone, 10 billion meetings are scheduled every year. It is a huge activity with a LOT of inefficiency to tackle. plans to stick to just the scheduling capability and to be the very best at that. Already Amy and Andrew Ingram have chatted to more than 500,000 people in their short lives, and the company is growing primarily by word of mouth.  

With $34 million invested, is a big bet. But Mortensen noted that a scheduling assistant needs to perform with a  high degree of accuracy. “If Amy or Andrew screw up, it’s not cool” -- which is why it's taken years of development to achieve the level of intuitive accuracy they deliver.  

And there are nuances to the way they communicate that make them seem human.  “It takes 13 meetings to fall in love with Amy,” promised Mortensen, and I would attest to that.

Lest I offend some people who have been very helpful to me over the years, I am not suggesting that Amy Ingram, a bot that manages schedules, compares at all to a real live executive assistant.  Amy will never think ahead to book a hotel for an upcoming trip, she won’t poke her head into my office to keep a meeting from running long, she won’t arrange a lovely catered lunch, she won’t convey my sentiments to people, and she won’t ever be someone I truly care about. For that, I’ll have to wait for Amy’s granddaughter.

But today, for $40 per month, Amy Ingram is putting some magic back into my calendar management. And that is money well spent.

2 comments about "The Magic Of AI -- And Amy Ingram".
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  1. Maarten Albarda from Flock Associates (USA), July 7, 2017 at 3:11 p.m.

    Hey Sarah: I, too, have used Amy. She is a miracle worker most of the time. But just like any other person learning how to read and make independent decisions, she is not without mistakes. 

    The other day, a participant in a call scheduled by Amy, sent me and Amy an email that he was running behind and could we start 15 minutes later. I was fine with that, but Amy, not grasping that the call was going ahead but a little later, messaged me that the other party had let her know he was now unavailable at the scheduled time so she had gone ahead and cancelled the call, and was looking to reschedule.

    Confusion ensued and I managed to let the other party know that 15 minutes later was OK. I think Amy is now still trying to reschedule the call even though it took place already...

    It is the first mishap I have encountered, and I will let the developers know. Perhaps they can tweak Amy's learning algorithm appropriately. Other than this incident I have been impressed!

  2. Sarah Fay from Glasswing Ventures, July 8, 2017 at 10:22 a.m.

    Maarten, you are absolutely right.  I wrote this column a while ago and came to realize Amy's limitations - I have had similar incidents.  Amy works best when there are predictable parameters to your schedule, meeting places and modes of communication, but it is difficult to deviate or communicate changes through her.  As such, I default to Amy for some meetings, but do it the old fashioned way when it's important, or involves nuances that need to be worked out with the other party.  Still for $40 / month the convenience of not needing to go back and forth for many meetings is worth it, yes?

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