Apps for Success - Calendly

Each month, John Bowman picks a new cool piece of technology that helps Customer Success Managers be more productive. We call it “Apps For Success” and in this review (#8) he takes a closer look at Calendly. 

This month we’re going to focus on a quick win to help you schedule a meeting: a public calendar link! 

We all have meetings. It’s just the nature of our job. You have to meet with your customers, with your coworkers, with your boss, or with your friends for lunch! The worst part of booking a meeting is finding a time that works for all parties involved. 

You either have to send emails back and forth listing your available times or call just to do the same thing. And don’t get me started on if there are more than 2 parties involved! The logistics of setting a meeting can be a nightmare. 

Calendar link apps come to the rescue because they allow the other parties to see the times you have available, pick the time that works for them, send a calendar event to each of your calendars, and even include instructions for how to join the meeting! There is no more need for back and forth because it allows the recipient to pick what works best on their terms. 

We will be looking at Calendly but there are a number of other alternatives out there. Don’t like Calendly? Check out Bookings by MicrosoftScheduleOnceIntercom’s booking, or Meetingbird. Each has different strengths and weaknesses but we choose Calendly because it’s got a large market share. 

[Standard disclaimer here. I own no part of any of the productivity apps for Customer Success Managers I’ll be reviewing in this column. The opinions contained in this review are mine and mine alone. SuccessHACKER is kind enough to lend me their microphone. If you happen to disagree, leave a comment and let me know! I love a good spirited debate.]

On to the app. Please enjoy my video review below.


What do you like best?

I love that Calendly because it sits in your email messages and allows your meeting parties to complete the intended action without having to leave their email. There is a term in manufacturing called “Point of Use.” It basically means you keep the tools you need to do the job, in the physical location where you do the job. You keep your tools at the point where you use them. Whenever you book a meeting with Calendly, you book it right where you need to do the job!

This app has a lot of synergy with another app we reviewed AutoTextExpander. I use AutoTextExpander to store all of the URLs I need to use on a regular basis, including my calendar links and those of my coworkers!

What do you dislike?

I hate that meeting link apps require customers to do more work! This isn’t something specifically against Calendly because all of these apps work the same way. They require the person you share your link with to do the work to find the times that work for the both of you. I love that I don’t have to do that work! But I really wish I didn’t have to offload it to customers. 

What business problems does the product solve? 

Calendly solves the problem of coordinating meetings between parties. There is no longer a need to email back and forth or play phone tag to set your meeting time. 

You benefit by you reducing the amount of back and forth necessary to set up a meeting. You also minimize the chances of double booking because these apps take into account events already on your calendar. Finally, when someone uses your calendar link, the app will automatically send an event to the customer's calendar with your preferred instructions for joining the meeting. 


Calendly, and apps like it, make booking a meeting with someone more efficient and reduce the need to go back and forth to nail down a time. Using a meeting booking app is a quick win for your team to become 1% better.  It’s not going to revolutionize the way your team interacts with customers, but this is a real efficiency gain which will make your lives easier!

Calendly has a free option (and so do most others) so give it a shot!

Have another favorite app for scheduling meetings? Put it in the comments below. I’d love to hear about it!  

About the Author


John Bowman

John Bowman, Esq., is the Director of Customer Success at Jetpack Workflow. He is a rising star in the Customer Success community, leading the The Pittsburgh Customer Success Meetup and the Pittsburgh Gainsight Pulse chapter, as well as moderating the Customer Success Subreddit. John utilizes his 10+ years of professional experience to focus organizations on one goal: the customer's desired outcome.