Calendly is a scheduling software for organizing meetings and appointments between individuals and their clients or colleagues.

All-in-one scheduling platform for you to take appointments, sell your services and manage your business.

Book Like A Boss is an all-around tool that does a lot more than just bookings. It’s a fully integrated web-building platform centered around your booking calendar. Calendly is very calendar focused. That may be fine for some people, but if you’re a serious service provider you may need to think about other extensions your booking tool can offer. Please continue to read on and find out more about our Calendly Comparison as follows.


Booking Page

Book Like A Boss and Calendly both let you upload a profile picture and a bio. But is that really enough to sum up everything your service has to offer? What about a “Products and Services” section that lets your clients purchase directly from you?


Book Like a Boss lets you add even more relevant information to your site such as your contact info, Skype ID, website, and other important links. Address your customers’ needs with an FAQ page. Go beyond a basic profile picture with a YouTube Introductory Video and a full photo gallery. If you want your booking page is more than just a calendar, only Book Like A Boss offers you the services you need.

Features Calendly Book Like A Boss
Profile photo
Introductory paragraph
Calendar that customers can use to book appointments with you
“Products & Services” section for selling your products and services
Photo gallery
“FAQs” section
Sidebar you can use to show your Skype ID, address, working hours, website links, and more
Introductory YouTube video
Cover (background) photo

Calendar Integrations

You expect almost any site these days to integrate with your personal and business calendars. From Gmail to iCal and from Microsoft’s Office software to their 365 fleet, Calendly and Book Like A Boss both live up to that expectation. Book Like A Boss also integrates with Microsoft Exchange.

Calendar Provider Calendly Book Like A Boss
Google Gmail
Apple iCal
Microsoft Outlook
Microsoft Office 365
Microsoft Exchange

Account Management

This is where Book Like A Boss really shines. From the fonts to the footers, you can fully customize your site with plans that turn virtually every step of the design process over to you. Integrate the premium apps that you use on a daily basis. Book Like A Boss supports Facebook, YouTube and MailChimp, sites that you use every day and that boost your sales and site traffic. Only Book Like A Boss supports customer messages and product orders directly through your booking page.

Calendly Book Like A Boss
Calendar appointments
Account settings
Booking page design
App integrations
Customer messages
Product/service orders
Embeds for other websites
Appointment analytics


When you’re paying for premium service, you expect a company to have your back. Book Like A Boss offers high quality, customer-oriented training videos, and tutorials. Get answers to your questions through chat or email. Plus, only Book Like A Boss offers Facebook support.

Calendly Book Like A Boss
Knowledge Base
E-mail Support
Website Chat Bubble (response within a few hours)
Video Tutorials (step-by-step)
Facebook Support


Each software provider offers the following pricing:

Plan Name Calendly Book Like A Boss
Basic (free) Plan
(Free account with basic features)
Premium / Espresso $8/user/month (annual billing) or $10/user/month (monthly billing) $9/month or $90/year (14 DAY TRIAL)
Pro / Mocha $12/user/month (annual billing) or $15/user/month (monthly billing) $12/month or $120/year (14 DAY TRIAL)
Cappuccino $19/month or $190/year (14 DAY TRIAL)
Latte $29/month or $290/year (14 DAY TRIAL)

The Stack Up

So far, we’ve seen what Book Like A Boss has to offer that Calendly doesn’t. But how do the two compare on their common features?


The Pics

The ability to upload a high-quality, high-res photo is important. Whether it’s your logo or a professional headshot, this is the first image your customers will see. Book Like A Boss lets you upload a picture of your choice and formates your pictures into a symmetric and ideal. As long as the pictures is greater than a 200×200 pixel square, Book Like A Boss can use it. Calendly, on the other hand, can accommodate up to a 5 MB file that you can crop yourself. That cropped image is then cropped again by the system into a circular shape. Not better or worse, necessarily, but the circle may cut your image or logo short or force you to zoom out far enough to be able to see all of it.

The Bios

With Calendly you get 255 characters in your welcome message. With Book Like a Boss you get a 50-character title, plus an About Me section and a Sidebar each with unlimited wordcounts.
Book Like A Boss also lets you add even more information with a level of granularity unavailable from competitors. Connect your Facebook, Twitter, LinkedIn and Instagram accounts with handy pre-generated fields. Choose to add a business phone number, email address, local time-zone, and even your local currency in case you do international sales.

The Integrations

Both sites feature lots of app integrations. Both feature Zapier, giving you access to loads of the apps you need for your business. Book Like A Boss goes a step further, however, and builds app functionality directly into its features. For example, you can create a service package you’d like to sell on your page. You can set this to automatically create a Zoom meeting as soon as the booking is secured. Does your booking service just “connect” to other apps? Or does it actually integrate them like Book Like A Boss does?

Mobile Apps

Calendly offers a mobile app for iPhone, a desktop app for Windows and a browser extension for Google Chrome. No Android app currently exists.
Book Like A Boss has a mobile-friendly webpage. Create a bookmark for your homepage, place it on your home screen, and access it anywhere on any device. Whether you’re using a PC, tablet, iPhone or Android, you get a clean, streamlined layout designed to work wherever you need it.

Pros of Calendly

Calendly is simple, straightforward and easy to use. The free version may be all you need if your business just requires a simple booking platform and not much else. But ask yourself, what is in the paid versions? Or, more importantly, what isn’t there?

Pros of Book Like A Boss

Book Like A Boss is a powerhouse. It is a website, a booking site, and an online store. It can function as whatever your service needs. Book Like A Boss will always be able to work for you because you design it. While offering a massive selection of unique features, it remains simple and easy to use with an intuitive interface for both you and your clients.