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Software · head to head

Calendly vs Squire

Calendly logo

Calendly

Software

Scheduling automation platform for eliminating back-and-forth

From
Free
Rated
-
Full reviewWebsite
Squire logo

Squire

Software

The operating system for barbershops

From
$30/month
Rated
-
Full reviewWebsite

The short version

  • Only Calendly has a free tier, so it costs nothing to try first.
  • Each has a real cost: Calendly the free plan allows one event type and one calendar connection, so it cannot handle different meeting formats; Squire booking fees of $1-3 per appointment add significant cost beyond subscription, increasing total cost of ownership
  • They diverge on capability: Calendly covers Calendar sync, Squire covers Online booking.

Where they differ

Only the attributes on which Calendly and Squire actually diverge.

Attributes where Calendly and Squire differ
AttributeCalendlySquire
Starting priceFree$30/month
Free tierYesNo
Founded20132015

Identical on both: pricing model (Unknown), platforms (Web, iOS, Android), user rating (Not yet rated), category (Unknown).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Calendly

  • Calendar sync
  • Automated scheduling
  • Custom availability
  • Time zone detection
  • Reminder emails
  • Buffer time
  • Meeting polls
  • Embed on website

Only in Squire

  • Online booking
  • Walk-in queue
  • Point of sale
  • Team management
  • Instant payouts
  • Client app
  • Marketing tools
  • Business analytics

What people use each for

The jobs each tool is most often brought in to do.

Calendly

  • Sales meetingsnot Squire
  • Interview schedulingnot Squire
  • Customer callsnot Squire
  • Office hoursnot Squire
  • Webinar registrationnot Squire

Squire

  • Barbershop managementnot Calendly
  • Walk-in handlingnot Calendly
  • Team payrollnot Calendly
  • Client bookingnot Calendly

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Calendly

  • The free plan allows one event type and one calendar connection, so it cannot handle different meeting formats
  • Automated reminders and multiple calendars need Standard at $10 per seat per month
  • Round-robin routing, lead qualification and Salesforce integration require Teams at $16 per seat per month
  • SAML single sign-on, audit logs and domain control are Enterprise only, starting at $15,000 a year
  • Advertised prices are the annual rates

Squire

  • Booking fees of $1-3 per appointment add significant cost beyond subscription, increasing total cost of ownership
  • Limited to barbershops and beauty salons; not suitable for other service industries
  • Walk-in and waitlist features only available on higher-tier plans, limiting functionality for drop-in appointments
  • POS system tightly integrated; cannot use with alternative payment processors or systems
  • Customer data locked into Squire platform with limited export options

Pricing, plan by plan

Calendly

Free
  • FreeFree
    • 1 event type
    • 1 calendar connection
    • Basic confirmation email
  • Standard$10/month
    • Unlimited event types
    • Multiple calendars (up to 6)
    • Integrations with HubSpot, Mailchimp, Stripe, PayPal
  • Teams$16/month
    • All Standard features
    • Salesforce integration
    • Round-robin meetings
  • Enterprise$15000/year
    • All Teams features
    • Salesforce routing lookup
    • Microsoft Dynamics 365

Squire

$30/month

No published plan breakdown. See the Squire review.

Which should you pick?

Choose Calendly if

  • You need calendar sync.
  • You want to start without paying.
  • You work on Web, iOS, Android.
  • You also want automated scheduling.
Calendly review

Choose Squire if

  • You need online booking.
  • You work on Web, Ios, Android.
  • You also want walk-in queue.
Squire review

Questions people ask

Is Calendly or Squire better?
Neither clearly leads. Calendly starts at Free and Squire at $30/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Calendly or Squire?
Calendly has a free tier; the other does not. Paid plans start at Free for Calendly and $30/month for Squire.
Does Calendly or Squire run on more platforms?
Calendly runs on Web, iOS, Android. Squire runs on Web, Ios, Android.
Can I use Calendly for free?
Yes. Calendly has a free tier, so you can try it without paying. Squire starts at $30/month.
What is Calendly best used for?
Calendly is most often used for sales meetings, interview scheduling, customer calls, office hours. Of those, sales meetings and interview scheduling are not what Squire is typically brought in for.
What can Calendly do that Squire cannot?
Calendly covers Calendar sync, Automated scheduling, Custom availability, Time zone detection. Squire covers Online booking, Walk-in queue, Point of sale, Team management.

Answered from the vendors’ own pages

Calendly: Does the free tier include automatic reminders?

No. The free plan only includes a basic confirmation email when someone books. Automated reminder workflows, SMS reminders, and follow-up sequences require the Standard plan ($10/month or higher).

Source
Squire: What are Squire's pricing tiers?

Squire offers Pro plans starting at $30/month for independent barbers, Pro-Complete at $100/month for full shops, Executive tiers at $100-150/month, and Titan at $250/month. All include scheduling, POS, and customer management features.

Source
Calendly: Can I offer multiple meeting types on the free plan?

Only one event type can be active at a time. You can create multiple event types, but only one booking link works simultaneously. Switching between different meeting lengths requires manually activating another event type.

Source
Squire: Does Squire charge booking fees?

Yes, Squire charges customers $1-3 per booking for online scheduling, in addition to the monthly subscription cost. This is a key cost factor beyond the base subscription.

Source
Calendly: Does Calendly work with Apple Calendar and iCloud?

No longer for new users. As of August 20, 2024, new users cannot connect iCloud or Apple Calendar. Existing connections continue to work, but Calendly ended support for new Apple Calendar integrations citing Apple's security changes.

Source
Squire: What integrations does Squire support?

Squire integrates with Square, QuickBooks, Google Calendar, and Stripe. It also offers an API for custom integrations and works with Zapier to connect to hundreds of other applications.

Source
Calendly: What platforms can I use Calendly on?

Calendly is available on Web, iOS, and Android. Browser extensions are available for Safari. There are no dedicated Windows or Mac desktop applications.

Source
Squire: What core features does Squire provide?

Squire includes online appointment scheduling, integrated POS system, customer relationship management, loyalty reward programs, promo codes, and automated text reminders.

Source
Calendly: What does the Standard plan ($10/month) add over free?

Unlimited event types, multiple calendar connections (up to 6), integrations with HubSpot, Mailchimp, Salesforce, Stripe, PayPal, Zapier, and webhooks, plus automated reminders and email sequences.

Source
Squire: Does Squire support walk-in customers?

Yes, Squire supports walk-in booking through its waitlist feature, which is available on all plans except the basic Pro tier.

Source
Squire: Who founded Squire and how is it backed?

Squire was founded by Songe LaRon and Dave Salvant in 2016. The company raised $162M in funding as of February 2026 and achieved a $750M valuation in 2021.

Source
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Related pages

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