Software · head to head
Calendly vs Gladly

Calendly
Software
Scheduling automation platform for eliminating back-and-forth
- From
- Free
- Rated
- -
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; Gladly no pricing is published at any level, and the pricing page states no per agent cost, per conversation rate, minimum commitment or feature tiers
- They diverge on capability: Calendly covers Calendar sync, Gladly covers Lifelong conversation.
Where they differ
Only the attributes on which Calendly and Gladly actually diverge.
Identical on both: 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 Gladly
- Lifelong conversation
- Omnichannel support
- Customer timeline
- Task management
- Knowledge base
- IVR
- Shopify
- Magento
Both cover
- Salesforce
- Stripe
- SOC2
- GDPR
What people use each for
The jobs each tool is most often brought in to do.
Calendly
- Sales meetingsnot Gladly
- Interview schedulingnot Gladly
- Customer callsnot Gladly
- Office hoursnot Gladly
- Webinar registrationnot Gladly
Gladly
- Customer service built around a single customer record rather than ticketsnot Calendly
- Handling support conversations across voice, messaging and emailnot 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
Gladly
- No pricing is published at any level, and the pricing page states no per agent cost, per conversation rate, minimum commitment or feature tiers
- The pricing page presents outcome statistics in place of any cost information
- Every route to a figure goes through a demo or sales conversation
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
Gladly
$180/month- Hero$180/month
- All channels
- Customer timeline
- Knowledge base
- Superhero$210/month
- Everything in Hero
- Custom reporting
- Advanced rules
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.
Choose Gladly if
- You need lifelong conversation.
- You work on Web, Ios, Android.
- You also want omnichannel support.
Questions people ask
- Is Calendly or Gladly better?
- Neither clearly leads. Calendly starts at Free and Gladly at $180/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
- Which is cheaper, Calendly or Gladly?
- Calendly has a free tier; the other does not. Paid plans start at Free for Calendly and $180/month for Gladly.
- Does Calendly or Gladly run on more platforms?
- Calendly runs on Web, iOS, Android. Gladly runs on Web, Ios, Android.
- Can I use Calendly for free?
- Yes. Calendly has a free tier, so you can try it without paying. Gladly starts at $180/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 Gladly is typically brought in for.
- What can Calendly do that Gladly cannot?
- Calendly covers Calendar sync, Automated scheduling, Custom availability, Time zone detection. Gladly covers Lifelong conversation, Omnichannel support, Customer timeline, Task management. Both handle Salesforce, Stripe, SOC2, GDPR.
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).
SourceCalendly: 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.
SourceCalendly: 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.
SourceCalendly: 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.
SourceCalendly: 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.
SourceRelated pages
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- Gladly vs GlossGenius
- Gladly vs Schedulicity
- Gladly vs Square Appointments
- Gladly vs When2meet
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- Gladly vs Airbnb
- Gladly vs Booker by Mindbody
- Gladly vs Kustomer
- Gladly vs Front
- Gladly vs Groove
- Gladly vs Freshdesk
- Gladly vs Freshworks Customer Service Suite
- Gladly vs Jira Service Management
- Gladly vs Salesforce Service Cloud
- Gladly vs Zendesk
- Gladly vs 8x8 Contact Center
- Gladly vs Amazon Connect
- Gladly vs BMC Helix
- Gladly vs Chatwoot
- Gladly vs Customerly
- Gladly vs DelightChat
- Gladly vs Dialpad Contact Center
- Gladly vs Dixa
- Gladly vs Freshservice
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