Boosting your sales productivity with an AI assistant

Before I started working at, I thought Amy and Andrew, our artificial intelligence personal assistants, were freakishly impressive and cool. Since I was hired in September as’s Enterprise Sales Manager, I’ve become so dependent on Amy that I know I couldn’t do my job nearly as well without her.

Any client-facing role, e.g. sales, business development, account management, must spend an obscene amount of time scheduling meetings. It turns out that Amy and Andrew, our AI personal assistants, are life-saving tools for salespeople. Yes, of course I’m biased (my job is to sell Amy and Andrew all day long). So don’t trust me. Trust the data. Amy has scheduled over 200 meetings for me in less than 3 months, saving me roughly 20 hours every month.

To help my fellow salespeople, I thought I’d share my best practices. (And really, what good salesperson doesn’t want to add 20 hours a month back into their calendar? Think how many more calls or demos you could do!)

Set preferences that map to your actual habits

Salespeople set up all different types of meetings—introductory discovery calls, product demonstration screen-shares, in-person negotiations. For Amy to set up meetings to your liking, she has to know what you like in the first place. One of the most important things you can do when working with Amy as a salesperson is to properly set up your preferences.

Because of the nature of our sales cycle, I tend to do a lot of fairly short calls. If I simply ask Amy to “set up a meeting,” she will set up a 30 minute phone call, since I’ve told her a 30-minute call is my default meeting type. She knows that I like to do coffee meetings at Gregory’s Coffee on Broadway and that I prefer 30 minutes of breather time on either end of an in-person meeting (I find that my in-person meetings almost always go longer than expected). Amy also knows that if I’m setting up a call she should asks my guests for their phone number because I’ve told her that I prefer to call them rather than the other way around. (You give Amy all of this vital information on

Each salesperson has their own preferences (and sales cycle), so it’s important to make sure that Amy and Andrew know not only how to be a good personal assistant, but how to be your best personal assistant.

Prospecting diligently versus spamming your lead list

Amy excels at setting up meetings; however, she’s deliberately designed to set up only verified meetings. These are meetings that both you AND your guest (e.g. prospect) have agreed to take.

One of Amy’s strengths is that she doesn’t drop the ball (which, let’s face it, we all inadvertently do every once in awhile); she’ll always follow up with your prospects to make sure that a meeting gets on the calendar. Her persistence is a key strength, but this trait will backfire if you’re trying to set up an unverified meeting. If you send out a batch of cold emails, Amy will reach out to all of those prospects, whether they’re interested in meeting with you or not. And she’ll reach out three times to each prospect before she gives up. If a prospect doesn’t want to take you up on a meeting, you’ve just clogged their inbox and made a pretty bad impression.

Instead, when I send out my initial emails to prospects, I include something along the lines of the following at the end of my note:

“I’d love to find some time to chat with you and discuss further. Let me know if you’re interested, and I’ll CC in Amy, my AI personal assistant, to get something on the calendar :).”

Then, when my prospects get back to me and agree to a meeting, I CC Amy into the conversation, and she gets right to work, like this:

“Awesome! I’m looking forward to it then. I’ve CC’ed in my AI assistant, Amy, to help us with scheduling. Amy, can you please set up a call for Ava and I next week?

Introducing Amy when you’re meeting with VIPs  

The biggest hesitation I hear from salespeople interested in using Amy is that they aren’t quite sure how their clients will react to being “passed off” to an AI assistant. I remember feeling the same way when I first got started with Amy. How do you hand a client over to Amy and still make them feel special? Now, I cannot not use Amy, regardless of how important the meeting is or whom I’m meeting with!

When I’m “meeting up” (e.g. meeting with someone who’s extremely important and higher in the social hierarchy than I am), I can signal to my contact that I understand their status by looping Amy into a conversation like this,

“Amy, can you please find a time for John and myself to meet next week? I’m happy to go outside my regular scheduling hours and would be happy to travel to his office.”

By explicitly offering to be flexible about time and location, I’m letting John know that I recognize he’s more important and hence should set the conditions of our meeting.

Over the past few months using Amy to schedule my sales calls and demos, I’ve found that most of my prospects and clients enjoy working with her as much as I do. They appreciate that Amy follows up with them about getting the meeting on the calendar if they forget to respond. They also appreciate the confirmation Amy emails them, as a reminder, if the meeting has been scheduled over 10 days ago. And in cases where people need to reschedule, they’re relieved that the work to find a new time falls on Amy rather than taking on that burden themselves or putting it back on me. And a few have told me had they not known I was working for, they would have mistaken Amy for a human!

Have any questions, thoughts, or tips of your own? Shoot me a note at any time! ?


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