Calendly
Calendly is an automated scheduling platform that eliminates back-and-forth emails by allowing others to book meetings directly on your calendar based on your real-time availability and custom preferences.
Square Appointments
Square Appointments is an all-in-one scheduling and point-of-sale software that helps service-based businesses manage online bookings, process payments, and track customer relationships from a single integrated platform.
Quick Comparison
| Feature | Calendly | Square Appointments |
|---|---|---|
| Website | calendly.com | squareupspace.com |
| Pricing Model | Freemium | Freemium |
| Starting Price | Free | Free |
| FREE Trial | ✓ 14 days free trial | ✘ No free trial |
| Free Plan | ✓ Has free plan | ✓ Has free plan |
| Product Demo | ✓ Request demo here | ✓ Request demo here |
| Deployment | ||
| Integrations | ||
| Target Users | ||
| Target Industries | ||
| Customer Count | 0 | 0 |
| Founded Year | 2013 | 2009 |
| Headquarters | Atlanta, USA | San Francisco, USA |
Overview
Calendly
Calendly simplifies the way you schedule meetings by removing the frustrating back-and-forth of email chains. You simply set your availability preferences, share your personal link, and let invitees pick a time that works for everyone. It automatically syncs with your existing calendars to ensure you are never double-booked and sends instant confirmations to all parties involved.
You can use it for everything from simple one-on-one check-ins to complex group sessions and round-robin sales calls. The platform handles the time zone conversions and reminder notifications automatically, so you can focus on the actual meeting rather than the logistics of setting it up. It scales easily from individual freelancers to large global enterprises requiring advanced security and team routing.
Square Appointments
Square Appointments is a versatile scheduling solution designed to help you run your service-based business more efficiently. Whether you are a solo practitioner or managing a large team, you can automate your calendar and let clients book their own sessions 24/7 through a custom booking website or social media integrations.
The platform goes beyond simple scheduling by integrating a full point-of-sale system directly into your workflow. You can accept payments, manage inventory, and track customer history without switching between different tools. It eliminates the headache of no-shows by allowing you to require prepayments or cancellation fees, ensuring your time remains profitable and your schedule stays full.
Overview
Calendly Features
- Calendar Sync Connect up to six calendars per user to automatically check your real-time availability and prevent any double-bookings.
- Automated Workflows Send automated thank-you notes, meeting reminders, and follow-up emails to your invitees to reduce no-shows and save time.
- Round Robin Scheduling Distribute incoming meetings automatically among your team members based on availability, priority, or equal distribution logic.
- Meeting Polls Vote on preferred times for large group meetings and let the majority decide the best slot without endless email threads.
- Custom Branding Remove the Calendly logo and add your own branding to booking pages for a professional, cohesive client experience.
- Payment Integrations Collect payments via Stripe or PayPal directly at the moment of booking to streamline your billing process.
Square Appointments Features
- Online Booking Site. Create a professional, custom-branded booking website where your clients can view your availability and book services anytime.
- Automated Reminders. Reduce no-shows by sending automated text and email reminders to your clients before their scheduled appointments.
- Integrated Payments. Process credit cards and digital wallets instantly with built-in payment processing that links directly to your appointments.
- No-Show Protection. Protect your time by requiring clients to enter a credit card on file or pay a deposit upfront.
- Staff Management. Manage multiple staff calendars, set individual permissions, and track performance metrics for your entire team in one place.
- Customer Directory. Keep detailed profiles of your clients including their appointment history, personal preferences, and previous purchase records.
Pricing Comparison
Calendly Pricing
- 1 calendar connection
- Unlimited one-on-one events
- One event type
- Automated event notifications
- Mobile app access
- Everything in Free, plus:
- Connect 2 calendars per user
- Unlimited active event types
- Group and collective events
- Reminders and follow-ups
- Custom branding on booking pages
Square Appointments Pricing
- For a single location
- Custom booking website
- Automated SMS & email reminders
- Unlimited staff accounts
- Square POS integration
- Credit card on file for no-shows
- Everything in Free, plus:
- Reduced payment processing rates
- Multiple location management
- Automated confirmations
- Google Calendar sync
- Advanced staff management
Pros & Cons
Calendly
Pros
- Eliminates repetitive back-and-forth emails effectively
- Automatic time zone detection works flawlessly
- Clean and intuitive interface for invitees
- Seamless integration with major calendar providers
Cons
- Free version limited to one event type
- Customization options restricted on lower tiers
- Workflows can be complex to set up initially
Square Appointments
Pros
- Seamless integration with the broader Square ecosystem
- Extremely easy setup for non-technical business owners
- Generous free tier for solo practitioners
- Reliable mobile app for managing bookings on-the-go
Cons
- Customization options for booking sites are limited
- Customer support can be difficult to reach
- Advanced features require moving to paid tiers