Chili Piper vs. Square Appointments

Overview
ProductRatingMost Used ByProduct SummaryStarting Price
Chili Piper
Score 8.7 out of 10
Mid-Size Companies (51-1,000 employees)
Chili Piper is scheduling and routing software for B2B revenue teams. Its products help revenue teams increase their inbound conversion rates, increase customer satisfaction, and reach new levels of productivity. The vendor states Companies like Twilio, Forrester, Spotify, and Gong use Chili Piper with the goal of increasing their inbound conversion rates, eliminating manual lead routing, and streamlining critical processes around meetings. Chili Piper…
$15
per month per user
Square Appointments
Score 10.0 out of 10
N/A
Square headquartered in San Francisco, California offers Square Appointments, appointment scheduling software. The software is based on technology acquired with BookFresh in February 2014.
$0
Pricing
Chili PiperSquare Appointments
Editions & Modules
Instant Booker
$15
per month per user
Handoff
$25
per month per user
Concierge Inbound Scheduling
$30
per month per user
Distro
Starting at $20
per month per user
Free
$0
Plus
$29
per month per location
Premium
$69
per month per location
Offerings
Pricing Offerings
Chili PiperSquare Appointments
Free Trial
NoNo
Free/Freemium Version
NoYes
Premium Consulting/Integration Services
NoNo
Entry-level Setup FeeNo setup feeNo setup fee
Additional DetailsOnboarding and Support are included at no additional charge.
More Pricing Information
Community Pulse
Chili PiperSquare Appointments
Considered Both Products
Chili Piper
Chose Chili Piper
I have only used the free version of Calendly so it is not exactly a fair comparison. With both of my experiences with this software Chili Piper feels more robust, especially with integrations. Chili Piper integrates with Outlook, Salesforce, and Zoom. These are the 3 …
Chose Chili Piper
This is only comparing the meeting scheduling functions of which Outreach was easier for our reps to learn and use. Otherwise they cannot really be compared.
Chose Chili Piper
Calendly was being used at the company by some other departments and still is to some extent. However adding Chili Piper fore the marketing and sales departments was a no brainer once we saw the demo. It's Calendly on steroids and the company is just getting started using it. …
Chose Chili Piper
I've used Drift and Salesloft scheduling tools. They all connect to google calendars, but Chili Piper is the only that I'm aware of that can insert time suggestions without actually blocking the time off as well as Round Robin assignment of meetings. Chili Piper has been the …
Chose Chili Piper
I prefer using Chili Piper as compared to Calendly. Both are great tools but Chili Piper seems to align better with our team needs.
Chose Chili Piper
In the past I have booked with Calendly, but were unable to set up a true salesforce integration, and were not able to set up a marketo integration. Calendly is great for a simpler flow or for a 1:1 scheduling app, but for our team that is made up of different regions and uses …
Chose Chili Piper
The end result was more in line with what we were looking for. Our main objective was to allow people to go to the website and explore our content, and then easily schedule a demo without having to wait for someone to call them and set something up. Chili Piper created the …
Chose Chili Piper
Way better tool and far easier to use than Calendly. This is the full bundle from rev/sales ops to daily use across AE's and SDR's
Chose Chili Piper
I personally have never had experience with a platform similar to Chili Piper prior to this year.
Chose Chili Piper
When we were vetting we didn't find a tool that would match Chili Piper in functionality.
Few Sales Enablement tools work with Events and can match some of its functionality, but that wasn't good enough for our needs:)
Chose Chili Piper
ChiliPiper is far easier to use for scheduling on someone else’s calendar. The ability to add a link in emails for people to schedule onto our calendars is nice as well. Neither of these things is possible in Outlook by itself, so it’s nice that it helps with those things.
Chose Chili Piper
As a startup Google calendars were adequate. But as the company grew, the ability to schedule multiple teams and even multiple sales team we had to have a way to allow a logical way to see and schedule the appropriate team. Also giving customers to schedule with certain …
Chose Chili Piper
Chili Piper meeting booking is superior to Outreach
Chose Chili Piper
The end result was more in line with what we were looking for. Our main objective was to allow people to go to the website and explore our content, and then easily schedule a demo without having to wait for someone to call them and set something up. Chili Piper created the …
Chose Chili Piper
It stacks up well. Much more logic and ability to customize workflows and logic than Calendly, for example. The integration with Salesforce is also very strong. If you need advance scheduling logic, this is one of the strongest options in the market in my opinion. The ability …
Chose Chili Piper
We actually have not used any products like Chili Piper as of yet here at PitchBook. In my last role at Onerent I also did not use Chili Piper... the closest thing that we used was part of outlook/salesforce capability.
Chose Chili Piper
It's not even close. Chili Piper is way more robust and effective. The support time is world class and promptly fixes issues.
Chose Chili Piper
We started with Calendly, but were unable to set up a true salesforce integration, and were not able to set up a marketo integration. Calendly is great for a simpler flow or for a 1:1 scheduling app, but for our team that is made up of different regions and use marketing …
Square Appointments
Chose Square Appointments
Square looks and feels more professional than Booksy, while requiring a card on file - something Calendly cannot do. I like that they are affordable and clients enjoying scheduling through Square Appointments. Scheduling an appointment works every time. The integration with …
Chose Square Appointments
Square Appointments is easier to use that other solutions from my experience. I find the user interface to be cleaner and more intuitive. I like the reminder features as well as suggested calendar blocks. It is helpful to have the option to show my time as free or busy, include …
Chose Square Appointments
Square Appointments is above outlook. Easily able to create appointments and do bookings. Never have to worry if I overbook, I will get an alert if it is done.
Chose Square Appointments
Though office can offer a lot of appointment base tasks. Square appointments seem to help keep track, with a more direct approach. It helps to declutter integrations and information, that can often get missed and feel to convoluted. It's approach is more specific in handling …
Chose Square Appointments
We have used another booking platform that is not listed here. We like the flat rate model and functionality of Square Appointments.
Chose Square Appointments
  • I have tried many of the Appointment scheduling systems out there. Honestly, there are many great ones out there, like Calendly, ScheduleOne, and Appointlet.
  • The reason Square Appointments is my choice is the ability to have an all in one solution. Hence, I have one software to …
Best Alternatives
Chili PiperSquare Appointments
Small Businesses
vCita
vCita
Score 8.5 out of 10
vCita
vCita
Score 8.5 out of 10
Medium-sized Companies
LeanData
LeanData
Score 10.0 out of 10
LeanData
LeanData
Score 10.0 out of 10
Enterprises
Zoom Workplace
Zoom Workplace
Score 8.4 out of 10
Zoom Workplace
Zoom Workplace
Score 8.4 out of 10
All AlternativesView all alternativesView all alternatives
User Ratings
Chili PiperSquare Appointments
Likelihood to Recommend
6.3
(0 ratings)
9.1
(0 ratings)
Support Rating
8.2
(0 ratings)
10.0
(0 ratings)
User Testimonials
Chili PiperSquare Appointments
Likelihood to Recommend
It is very well suited for anyone looking for a scheduling tool that integrates directly with Salesforce and/or Marketo, or other marketing automation platforms. Especially if you need to route to teams based on different regions or other criteria.There are other simpler scheduling tools out there, but this makes routing and tracking on the back end much easier with the best integration with other tools.
Read full review
Looking to automate and have something handle appointments with ease, then square appointments will suit you well. It brings various schedules, tasks and calendar appointments into one place and helps you keep on top of things. Can bring to your attention up and coming appointments, scheduling and meetings with out the need for checking through calendars and to do lists.
Read full review
Pros
  • The Google Calendar integration is seamless, a unique zoom link is also automatically created when a meeting is booked on my calendar.
  • The booking link is simple for my prospects and customers to find time on my calendar.
  • The chrome plug in is useful to use no matter what tab or page im sitting on.
Read full review
  • Square had good interoperability with Google Calendar, so all of our calendars were in sync.
  • Square Appointments we easy to use for clients, and with a few Luddite exceptions, worked flawlessly.
  • Square Appointments made it easy to schedule appointments without having multiple email messages or play phone tag with anyone.
Read full review
Cons
  • The ux interface could be easier to navigate for admins
  • The set up or meeting types could be more intuitive, as an admin I have had to help our reps set this up a lot as they have gotten confused
  • Chili Piper can have certain words they use like booker assignee which could be better defined in the onboarding process for reps
Read full review
  • Additional functionality: real-time availability calendar to customers
  • Not redirect away from our site to Square
  • Additional functionality: Ability for customers to add up sales when checking out
Read full review
Support Rating
  • Support was very responsive during our integration phase, and after that too.
  • They have the whole infrastructure built to notify customers about bug/outages, which is excellent. Entire System outage only happened once, but being updated on fix progress helped a lot to keep our team calm.
Read full review
  • Square Appointment is excellent at support! I have had several calls with them, and not one time have they dropped the ball, leaving me frustrated without a solution — not one time.
  • The community forum in Square Appointment can answer most of the questions, but if I have had real issues, I am always able to talk to a person. That is very valuable to me as a customer.
Read full review
Alternatives Considered
I've used Drift and Salesloft scheduling tools. They all connect to google calendars, but Chili Piper is the only that I'm aware of that can insert time suggestions without actually blocking the time off as well as Round Robin assignment of meetings. Chili Piper has been the easiest to use as a sales rep.
Read full review
Square Appointments is easier to use that other solutions from my experience. I find the user interface to be cleaner and more intuitive. I like the reminder features as well as suggested calendar blocks. It is helpful to have the option to show my time as free or busy, include when I am on vacation, and sick time.
Read full review
Return on Investment
  • More qualified opps
  • Increased efficiency. Much less time spent trying to line up availability etc. No more back and forth email chains trying to find times to meet.
  • Increased transparency. All meetings and Chili Piper events are logged directly in Salesforce for us.
Read full review
  • Square Appointments enabled us to deal with a large number of clients in a much more rapid time frame than we would have done otherwise.
  • Square Appointments has empowered us to go after other large organizations' business for photography sessions.
Read full review
ScreenShots