The top 3 best scheduling softwares of 2021 list is here.


Scheduling softwares should have one main goal: help ease the pain of scheduling. These softwares are not necessarily replacing all of the work, but they help fill the gaps and save some time. We believe there will almost always need to be some level of human interaction, but the softwares will help assist these efforts.


At Kyros, we for sure are using scheduling software and we wanted to go over the top 3 scheduling softwares with you and share some up and coming tools. PS: We are using Sidekick Ai (one of the up and coming tools)


1. Calendly.



Calendly just raised $350 million this year, putting them at a $3 billion valuation. You can basically say they are the industry leader in schedule softwares. Their software helps individuals, teams and companies with scheduling by allowing users to share their availability with custom configurations.


Key Features


  • Calendly is really easy to use. They have a simple interface so non techy users can easily start scheduling with their software.
  • They have a lot of integrations built into their software to help automate work flow processes.
  • After meetings are booked, it automatically updates calendars and sets reminders.
  • Users can accept payments to the booking pages.




  • You can only add up to 6 calendars per 1 user.
  • It is still a pretty basic scheduling tool where you only can share a page. They basically offer one type of way to schedule a meeting.


Overall this is a pretty good value for people who want a simple, easy to use scheduling software. They didn’t become a $3 billion company out of luck.


2. Chili Piper



Just like Calendly, Chili Piper just raised $33 million this year. Chili Piper’s scheduling software is a little more advanced and has more focus on driving revenue for teams. They focus on Demand Generation, Sales, Revenue Operations, Customer Success and Management. They have unique features for each category and more robust workflows.


Key Features


  • They have scheduling event pages like Calendly does.
  • They have many robust integrations like Salesforce to help automate workflows.
  • They have built out many other focuses per company department that help with specific needs.
  • Group meeting capabilities and meeting reminders.




  • The pricing isn’t as affordable as some other solutions.
  • They seem to be most focused on sales and revenue. So if this isn’t your focus, probably not for you.


Chili Piper is a great scheduling tool, if you are in sales and love workflow automation. But if you want something more simple and easy to use, this probably is not the best tool in your toolbox to use.


3. is a more sophisticated scheduling software that offers way more than just link share scheduling like the previous two. However, they do still offer the simple link share booking page as well. was actually recently acquired for an undisclosed amount. They have been around for 7 years and have raised millions of dollars from some large investment firms.


Key Features


  • A custom email scheduling bot you can work with to schedule a meeting.
  • They offer features for teams as well as individuals.
  • With their sophisticated email Ai scheduler, they also offer booking pages.
  • Lot’s of integrations to build workflows.




  • The Ai scheduler does not read emails or text, you basically CC it and give it pre built commands.
  • Needs feature improvement to be true Ai scheduler.
  • UX could use some love.
  • They just sold. So the main question is will the improve or roll up their system into the larger company?


Overall, is a step ahead of most when it comes to more sophisticated ways of scheduling that are smarter. However, they still have work to do but they did recently just sell their company so will they just roll it up in the larger company or keep improving upon it? We will see.


Bonus – 4: Sidekick Ai (Up and Coming)


Free Scheduling Software Sidekick Ai


Sidekick Ai would be described as a scheduling software above Calendly and just less sophisticated as a personal assistant. Really, would be the closest company but each company has a different way of scheduling. Sidekick Ai has a true machine learning, language processing AI built in. One main feature is called Forward to Schedule. You can literally forward an email to Sidekick, it will read it and book a meeting.


Key Features


  • Sidekick offers multiple ways for users to schedule, not just link share.
  • It was built for everyone, not just focused on niches like sales people.
  • The platform has a true language processing Ai like no other scheduling tool on the market.
  • Sidekick is really affordable right now because it’s so new.
  • You can add unlimited calendars to your account versus limitations like Calendly or Chili Piper.




  • It is only 12 months new, so it has a lot of improvements to make.
  • The web app needs to be more mobile friendly.
  • They need to build more integrations like iCal & Teams.


Overall, Sidekick Ai is a great tool if you want something more than just link share scheduling. They also do offer Scheduling Pages (their version of Calendly). This platform is new, but has a lot of potential. They are featuring a deal on AppSumo for $59 for one year access, which is a huge discount. It looks like they have big plans ahead, definitely one to keep an eye on. If you are a new adopter of tech, try them out.


We hope you enjoyed our list of the top 3 best scheduling softwares in 2021.


Here is an article you might enjoy Р5 Business Tips for Building a SaaS company 


About Kyros Digital


We are a software development company in Grand Rapids, Michigan. We have a true passion for problem solving by building useful software for the world. We are always learning and pushing ourselves to learn new tech stacks, trends and standards. We have won some awards, built some cool projects and are head down focused on our projects.

You can learn more about us or check out some work we have done.