18 Scheduling App Hacks That Will Change Your Life

Daniel Threlfall

A scheduling app can be a major game changer.

It can accelerate your speed to lead time, send a consistent stream of qualified leads to your sales reps, automate onerous manual tasks, and help close more deals. 

In short, it can light a fire under your SaaS. 

Here are 18 scheduling app hacks that will help you get the absolute most out of your platform and book meetings like a well-oiled machine.  

Automatically Add Meetings to a Rep’s Calendar with a Scheduling App

Let’s start from the top. 

Making a rep manually add each meeting to their calendar is laborious and a colossal waste of time. 

Luckily, a scheduling app like Chili Piper will do this automatically and sync meetings up with their calendar.

That way they’re always in the loop and are able to reach out to leads in a timely manner. 

Just choose times of availability — for example, a rep may be able to have meetings between 9 am and 1 pm in your time zone — and Chili Piper will use this information to ensure meetings are scheduled accordingly. 

Send Slack Notifications

As of late 2019, there were around 12 million Slack users

And judging by this graph from Statista, that number will only continue to grow. 


If you’re a company that uses Slack for keeping everyone on the same page (and sane), you can make things much more efficient by having notifications sent through Slack.

For instance, Chili Piper’s Slack integrations can notify a rep of the date and time of a meeting, while taking time zone differences into account and who the meeting is with.

And on the sales manager’s end, they’ll be notified whenever someone books a meeting with Instant Booker, when a meeting is rescheduled, when an instant live call is assigned, and more.  

Send Multiple Automated Reminders to Leads

The dreaded no-show continues to be a thorn in the side of many sales reps. 

Fortunately, this is something that can largely be avoided by sending automated reminders at key times.

Here’s the formula that we’ve found to work best when using Chili Piper

Send the first reminder one day prior to the meeting using an email template like this if a lead hasn’t accepted the meeting. 

Then, send a second reminder an hour before the meeting that looks like this. 

Finally, send a third reminder one minute before the meeting that looks like this. 

This helps keep leads dialed in, and using this particular formula has helped us keep our no-show rate below 2%

With Chili Piper, you can easily automate these reminders according to your personal preferences and simplify your rep’s life. 

Create an Automated Sequence For No Shows

If you still have a no show, automating the process for handling them lessens the blow and helps sort everything out without wasting anyone’s time. 

So, the end result is that the lead receives a message like this allowing them to conveniently reschedule. 

You can see how an automated sequence works on this resource from Chili Piper

And that brings me to my next scheduling app hack. 

Offer One-Click Rescheduling

Using a platform like Chili Piper comes with a built-in rescheduling option that allows a lead to reschedule with just a single click.

This prevents hot leads from slipping through fingers and takes the pain out of rescheduling. 

Use Round Robin Routing to Crank Up Your Speed to Lead Time

The methodology you use to route qualified leads to reps will have a huge impact on your conversion rate. 

After all, responding within one minute increases your chances of converting by a staggering 391%

But if you wait an hour, that number drops to 36%, and if you wait a day, it goes down to 17%.

A simple scheduling app hack to streamline routing is to use round robin rules, where leads are distributed evenly moving in a rotation like this. 

That way you can seamlessly cycle through your list of reps, giving everyone a fair chance, while keeping your routing laser fast. 

And with Chili Piper, you can fine tune your round robin rules to fully optimize the process and get it just right. 

For example, you can adjust the weight for each rep. 

And you can create vacation days when needed.

Use Premade Meeting Templates on a Scheduling App

Needless to say, the quicker and more streamlined the communication is between your salespeople and leads, the better things will be.

While you obviously want to maintain a personal touch, having to write everything out from scratch during interactions like discovery calls, before demos, and follow-ups can become tedious in a hurry. 

However, using premade templates is a simple scheduling app hack that will keep the communication flowing without eating up a ton of your reps’ time. 

With Chili Piper, reps can easily access their meetings in Instant Booker.

Then, they can use meeting templates like these.

This will make their lives much easier and help maintain consistency during their interactions with leads.

To see how Instant Booker can help assist with scheduling, check out this video featuring Madeline Anderson, Business Operations Administrator at Buildertrend. 

Use Hot Handoffs for Piping Hot Leads

Here’s the scenario.

An SDR has a sizzling hot lead on the phone, and they want to speak with an AE right away.

They’re showing a high intent to buy, so you don’t want any delays that could potentially cool the lead off. 

In this situation, a scheduling app like Chili Piper allows for hot handoffs that allow an SDR to handoff a meeting to an AE in real-time. 

They simply click the fire icon. 

Then, Chili Piper will load the instant booker, which will show the next available rep in the queue, and they can make the handoff. 


The piping hot lead is smoothly handed off and poised to convert. 

Automate Follow Ups After a Meeting is Scheduled

Just a little while ago I mentioned how you can use a premade template to streamline follow ups. 

But you can take it one step further by automating follow ups after a lead has scheduled a meeting.

Chili Piper is a scheduling app that makes this process super straightforward, where you just follow a few basic steps in the admin section. 

And when you’re done, you’ll have a template that looks like this and is sent automatically instead of forcing a rep to do it manually. 

This can save a massive amount of time and ensures smoother interactions with leads right from the start. 

Book Meetings From Your Social Accounts

The bulk of your leads will likely find your booking link on your website. 

But you can cast a much wider net and generate a far higher number of qualified meetings by placing your booking link on your social media accounts.

In fact, studies have found that some brands find up to 37% of their customers this way. 

And it makes sense.

If someone is checking out your Instagram page, for example, they’re doing their research and are already warming up to you.

So why not make it dead simple for them to set up a meeting and learn more right through your Instagram? 

This prevents them from having to go to your site, thus eliminating a step. 

In terms of the best performing social sites for generating online bookings, Instagram is at the top and Facebook is second. 

Book Meetings From Gated Content

“Roughly 80% of B2B content marketing assets are gated,” with the most popular types of content being eBooks, webinars, free trials, and product demos. 

Whenever someone fills out a form to access gated content, it means they’re performing active research and are often quality leads.

So, you definitely want to strike while the iron is hot with these visitors and book a meeting directly from the gated content, which is another feature you get with Chili Piper Concierge

Book Meetings From Email

Besides social media and gated content, you can also pull in more qualified leads by having reps add a booking link to their email signature.

This can be done by following a few easy steps with Chili Piper, and the signature will look something like this.

Just like that, a rep can schedule more qualified meetings with no extra effort. 

Plan on Monday Through Wednesday Being the Busiest Days for Meetings

Research has also found a clear pattern in terms of what days are most popular for scheduling meetings. 

Those days and Monday, Tuesday, and Wednesday, with Tuesday seeing the biggest number. 

Then, the number of scheduled meetings declines throughout the rest of the workweek and plummets on the weekend. 

So keep this in mind when using a scheduling app, and plan accordingly so that you always have enough manpower to cover the workload and let reps jump on leads while they’re hot. 

Set a Limit on Each Rep’s Availability

150 inbound leads is considered the sweet spot for each rep per month for the simple fact that it means they should be able to call or email every single lead. 

Asking a rep to go beyond that can leave them stretched thin and result in overload — something that can end up haunting you in the long run. 

Another scheduling app hack I recommend is to place a cap on each rep’s availability so you don’t run into this problem. 

This is something that can be done with many platforms, where you cap it at a certain number of bookings per day, such as 2 or 3.  

Or, you can always block off designated times throughout each day for a rep to work on tasks outside of meetings, such as planning, housekeeping, etc. 

Here’s an example of how this is done with Chili Piper

Keep a Bird’s Eye View on All Calendars

Let’s be honest.

Even with the best of planning and coordination, there’s always the potential for chaos, especially when you’re managing several reps at once. 

A scheduling app hack for keeping chaos at bay is keeping track of all calendars in one central location. 

You can think of it as a master calendar.

This is something else you can do with Chili Piper where you sync all of your rep’s calendars, so you always know what everyone’s availability is like and what’s going down on any given day. 

Increase Conversions By Reducing Form Fields

Generally speaking, the fewer number of fields you ask a prospect to fill out, the more qualified leads you’re going to get. 

The findings from this classic case study are proof. 

That’s why I always recommend trimming back form fields to the absolute minimum.

On the Chili Piper demo page, for instance, we only ask for three and it’s worked out perfectly. 


Let Leads Choose Options From a Dropdown Menu

You can take it one step further by letting leads choose from options in a dropdown menu rather than having to enter the information manually. 

Going back to the previous Chili Piper example, prospects can choose their CRM — Salesforce, HubSpot, or other — as well as their country from these two dropdown menus. 

This helps streamline things and eliminates unnecessary friction for a steady stream of leads. 

Offer Bookings in Different Languages

Only 20% of the world speaks English.

So, it’s important to account for the other 80% when using a scheduling app. 

Luckily, using a platform like Chili Piper offers a ton of different language settings — 31 to be exact — to support hyper-localization. 

You simply need to enable different languages to account for the markets you’re trying to reach. 

Scheduling App Hack FAQs

What exactly is a scheduling app hack?

It’s a shortcut used to help you fully leverage a platform and schedule all aspects of meetings more efficiently.

What are the benefits of using scheduling app hacks?

  • Increase your speed to lead time
  • Eliminate inefficiencies in the scheduling process
  • Simplify the lives of your entire sales team
  • Provide a better customer experience right out of the gate

Where can I find a list of Chili Piper hacks?

You can use the Chili Piper support resource to learn about the hacks mentioned here, as well as plenty of other useful features. 

Kicking SaaS and Taking Names

Scheduling apps have evolved like crazy in recent years.

And as we’ve just learned, there’s a huge list of features you can use to optimize and streamline nearly every aspect of meetings. 

From automatically adding meetings to a rep’s calendar to sending automated reminders to allowing leads to book meetings through a variety of different channels, using these scheduling app hacks should help you take your SaaS lead generation to the next level. 

Want a full overview on Chili Piper’s capabilities?

Ooh, Gimme a Demo!

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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