Best Scheduling Software 2020 | Honest Reviews

Daniel Threlfall

Scheduling software is growing by leaps and bounds and is expected to increase in market size from $205.85 million in 2018 to $564.31 million by 2026

Qualify scheduling software accelerates speed to lead time, helps reps be more productive, and ultimately helps close more deals.

But which scheduling software platforms are truly legit?

Here are my honest reviews of the best of the best. 

What Exactly is Scheduling Software?

First off, let me give you an official definition of what scheduling software is to make sure we’re on the same page.

Simply put, scheduling software is any online platform that allows you to book and manage meetings with leads.

Scheduling software automates and streamlines much of the process, so you can quickly book meetings with qualified leads and route them to the appropriate sales rep. 

These platforms also enable you to track and manage those meetings so you know what’s going on at all times. 

It takes the drama out of scheduling, so your team can focus on what’s most important — building rapport with targeted leads and moving them swiftly through the sales cycle faster

In turn, scheduling software helps turn more visitors into qualified meetings, and it’s been proven to have a dramatic impact on modern businesses. 

In fact, “a combined 61% of SMBs experience faster, easier, and more accurate scheduling using scheduling software.”

The numbers speak for themselves. 

Now let’s dive into the most standout platforms. 

Chili Piper

I can honestly say that Chili Piper is at the top of the totem pole when it comes to simplicity, intuitiveness, and booking meetings lightning fast. 

The whole purpose of Chili Piper is to automate the scheduling process, so you can route qualified leads to your sales team without making anyone jump through unnecessary hoops.

Here’s an example of how it works.

Say a visitor is interested in your product and wants to schedule a demo. 

Instantly after requesting a demo, Chili Piper allows them to choose a meeting time that’s perfect for them. 

They’re then routed to the right sales rep, based on predetermined rules.

Or, you can use basic round robin rules to distribute leads evenly — whichever you prefer.

The meeting is automatically added to the rep’s calendar. It’s that easy. 

You can also configure Chili Piper to send an automatic reminder to greatly reduce the odds of a no-show.

This makes your sales teams’ lives much easier, while simultaneously creating an amazing customer experience right from the start.


Next, there’s Calendly that’s designed to eliminate unnecessary phone and email tag.

It’s really simple to use.

Just let Calendly know what a rep’s availability is, share a link on your website or through email, and a prospect can select a time that’s convenient for them.

Leads can schedule individual time slots, or like with Chili Piper, you can use round robin routing to distribute them systematically to reps. 

Calendly automatically takes time zones into account and can set reminders. 

It also integrates with major calendar platforms like Google Calendar, Outlook, and iCloud.

Like I mentioned before, one of the biggest selling points of this scheduling software is its straightforwardness. 

However, that can also be a double-edged sword because many users would prefer to have features that were a bit more robust. 

And I personally think that it would be nice to offer some expanded functionality.

But all in all, Calendly is a solid platform that gets the job done, both for individuals and for teams. 


If you’re looking for a scheduling software that works for small to medium-sized business, as well as larger enterprises, AppointmentPlus should definitely be on your radar.

It allows you to scale with ease, which makes it a great fit for ambitious startups that forecast a lot of growth.

Here’s what you get with AppointmentPlus:

  • A cloud-based platform that allows prospects and customers to book appointments 24/7 with the touch of a button
  • Automatic reminders via email or text to minimize no-shows
  • In-depth reporting to give you a bird’s eye view of appointment history and product buying trends
  • An easy to use dashboard that puts you in the driver’s seat with scheduling

The main issue that I’ve seen with this platform is that it does take some time to configure the settings, which creates a longer learning curve than you’ll find with some other softwares. 

There are 500 different preference settings, making is highly customizable, but some people struggle to learn the ropes. 

That said, AppointmentPlus definitely has plenty of firepower, and once users get the hang of it, it’s an extremely helpful software that makes scheduling a breeze. 

Drift Meetings

Drift is a platform that offers a wide array of features — everything from account-based marketing to chatbots to sales video.

And of course, they offer scheduling with Drift Meetings, which allows you to automatically qualify and schedule meetings around the clock, whenever leads are interested. 

Or as Drift puts it, “you can still schedule qualified meetings for your reps even while they’re sleeping. So all they have to do is show up to the meeting.”

One of the more notable features is called Drift Playbooks, which lets you build a customized chatbot to qualify leads. 


Then, Drift automatically lets a lead choose a time on one of your rep’s calendars. 



There’s also Group Meetings where you can schedule meetings with more than two people at once. 

It’s all about creating a smooth, streamlined experience for leads and taking the headaches out of coordinating outreach for your sales team, making it a rock solid scheduling software through and through. 

In terms of drawbacks, the chief complaint users have is that the analytics is a bit limited and could be improved, but that’s certainly not a dealbreaker. 


Like Drift, vcita has several different features, including billing and invoicing, CRM, and email marketing.

But their bread and butter is their robust scheduling software.

It’s a self-service solution where leads can schedule meetings from your vcita landing page, as well as your Facebook page, which is a nice touch. 

Given that Facebook is such a marketing powerhouse and “32% of users engage with brands regularly” on this network, this can help turn your Facebook page into a legitimate source for qualified meetings.

With vcita, leads can quickly and conveniently select a time that’s ideal for them based on your team’s availability, and it will automatically confirm scheduling requests. 

This eliminates the mindless back-and-forthing that so many businesses succumb to these days and saves your team a ton of time.

On the back-end, reps can easily access their online scheduler, either through the vcita website or the app when they’re on the go. 

They can also set this platform up to receive real-time notifications whenever a lead requests a meeting and instantly respond. 

And to prevent no-shows, vcita sends automated meeting reminders through email or text. 

This scheduling software also makes it easy for sales managers to see what’s happening at any given time, and they can view each rep’s calendar and make changes when needed. 

Like Chili Piper, vcita makes it so leads don’t have to use a phone to call, and instead, they can speak with a salesperson via a video call through Zoom.

Finally, it’s one of the easier platforms to set up and something that can literally be done in just five minutes. 

When it comes to drawbacks, the main issue many people have is that the back-end navigation isn’t super intuitive and it takes some to figure it out.

This scheduling software has many of the same features as Chili Piper, Calendly, and Drift Meetings.

It connects with the calendars of your sales team and shares the times when reps are available to have meetings with leads. 

Leads simply pick a time that works for them, and they receive notifications, calendar invites, and reminders. automatically detects a lead’s time zone to prevent timing conflicts and coordinate friction-free meetings.

This platform integrates with both Google Calendar and Microsoft Calendar and provides you with your own personalized booking page. 

In fact, that’s one of the biggest things I like about it — that you can fully customize your booking page, using a design that jives with your branding for an ultra professional feel. 

I also like the fact that gives sales managers a bird’s eye view on what’s happening, enabling them to see each team member’s availability, the meetings they have scheduled, and more. 

As for cons, there’s nothing over the top, but having to manually perform repetitive tasks on here can be a little onerous at times (e.g. editing the titles of calendar events, incoming emails, and outgoing emails.)

Acuity Scheduling Software

Acuity is a full-service suite that checks all of the boxes.

It has a straightforward interface that allows leads to painlessly schedule meetings with your sales reps. 


That way quality leads don’t slip through your fingers, and you’re always in a position to strike while the iron is hot. 

Whenever a meeting is booked, a rep’s calendar is automatically updated and they receive a notification (Acuity syncs with popular calendars like Google, Outlook, iCloud, and Office 365).

It also adjusts for time zones and sends reminders so leads show up when they’re supposed to. 

And if there’s ever an issue where a meeting needs to be rescheduled, this can be done with just a single click without creating any drama for either party. 

Everything is completely customizable, which allows you to design Acuity to match your brand. 

I also like this software because of their intake forms, where you can grab important information ahead of time so reps go into each meeting fully prepared — something that’s vital to closing deals. 

Or as Fergal Glynn of Salesforce puts it, “Preparing for your sales demonstration is half the battle. You need to be focused, prepared for your specific audience, and convinced that you have done all that you can to get your prospect to view the demo as a valuable use of time.”

There’s really no glaring flaws with Acuity.

However, the back-end design leaves something to be desired and doesn’t have the same “pop” as similar platforms. 


The final scheduling software that deserves mentioning is Jifflenow, which allows you to hold several different types of meetings, including:

  • Product demos
  • Sales meetings
  • Roundtable discussions
  • Virtual sessions

Here’s what I like about it. 

Jifflenow automates and streamlines meetings to eliminate onerous manual scheduling.

Leads can use the smart Inbound Request Page to request meetings, while selecting a time slot that perfectly fits their schedule. 

It sends automated reminders so leads don’t forget, which slashes your no-show rate. 

It also has a built-in feature that identifies exact meeting purpose and opportunity information, ensuring reps are fully equipped for each interaction. 

I also like that it integrates with video conferencing platforms like Zoom, Microsoft Teams, and Webex, which means leads don’t even have to pick up the phone. 

And if you’re big on metrics, you’ll love the robust analytics that you get with Jifflenow. 

You can check out KPIs like influenced revenue from meetings, leader boards, ROI, and so on. 


That way you always know how much progress you’re making and who your top performers are.

Real-time motivation and recognition platform Hoopla adds that using leader boards can be especially beneficial because it naturally feeds competition and can lead to an uptick in productivity and sales. 

Most companies say that onboarding their reps on Jifflenow is pretty straightforward with a minimal learning curve.

However, many are underwhelmed with the lack of features and integration, which is the main downside. 

Scheduling Software FAQs

What is scheduling software?

“Scheduling software solutions are tools that allow professionals and businesses to better manage the scheduling of appointments and bookings.”

What are the benefits of scheduling software?

  • Automate the scheduling process
  • Increase your speed to lead time
  • Prevent scheduling conflicts
  • Free up reps’ time so they can focus more on selling
  • Make your sales team more productive
  • Create smoother lead interactions
  • Help your sales team close more deals

What are the most important features to look for in scheduling software?

  • Built-in lead routing
  • Calendar integrations
  • Automatic time zone adjustments
  • Automated reminders
  • Comprehensive analytics

Taking Meetings to a New Level With Scheduling Software

The expected compound annual growth rate of scheduling software is 13.1% between 2019 and 2026, meaning it’s a type of platform that’s being heavily used by more and more companies. 

And as you can see here, there are a ton of different options to choose from.

The ones I’ve listed here are the top dogs and can help you convert more visitors to qualified meetings without any drama or headaches. 

It’s just a matter of choosing a platform with the specific features you’re looking for and that allows you to schedule leads like a boss. 

Learn more on how you can use Chili Piper to qualify, route, and engage prospects and close more deals. 

Get a demo now.

About the author
Daniel Threlfall

I help SaaS and online businesses drive viral organic website traffic to double their organic traffic and revenue in 6-12 months.

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