Calendly Enterprise Review: Pricing, Features & Alternatives

Fernando Figueiredo
January 14, 2025
10
 min read
Contents

Looking to streamline your organization's scheduling process? You're probably familiar with Calendly as the go-to scheduling tool for small teams and individuals. But when it comes to enterprise-level needs, there's a lot more to consider. Let's dive into everything you need to know about Calendly Enterprise – from pricing and features to real alternatives that might better suit your needs.

We'll also cover Zeeg and its Enterprise option, a cost-effective and secure solution that will give you the peace of mind you need for less.

Calendly Enterprise Prices: Be ready to invest

If you're researching Calendly Enterprise, you're likely managing a larger organization with complex scheduling needs. The Enterprise plan's pricing structure reflects this, doing things different from Calendly's Standard option. The numbers are not as straightforward, as you can see:

  • Starting price: $15,000 per year
  • Minimum requirement: 30+ users
  • Per-user cost: Approximately $42 per month
  • Scalability: Costs adjust with user count, often with volume discounts

Good news: There’s room for negotiation

Here's something many don't realize – Calendly's Enterprise pricing isn't set in stone. Your organization can potentially secure better rates by leveraging, depending on some criteria, namely:

  • Feature package deals
  • Volume-based discounts
  • Longer contract commitments

Pro tip: Always ask about special pricing and try to negotiate – you might be surprised at the flexibility available for enterprise customers.

However, so far we've mostly talked about prices. But let's look at what you really get with Calendly Enterprise, whether it's worth it or not, and if there other alternatives out there that might translate into better investments.

Calendly Enterprise Features

Essential Scheduling Features

Every Calendly Enterprise subscription builds on the platform's core strengths:

  • Unlimited event types for maximum flexibility
  • Automated scheduling with smart rules
  • Up to six calendar connections per user
  • Seamless video conferencing integration
  • Robust email automation
  • Customizable booking workflows

Enterprise-Grade Capabilities

Here's where things get interesting. The Enterprise plan introduces several game-changing features designed specifically for large-scale operations:

Advanced Security and Authentication

  • SAML Single Sign-On (SSO) integration
  • SCIM provisioning for user management
  • Custom domain verification
  • Enhanced security protocols
  • Comprehensive audit trails

Powerful CRM Integration

  • Advanced Salesforce routing
  • Microsoft Dynamics 365 compatibility
  • Custom field mapping
  • Automated data synchronization
  • Lead routing optimization

Team Management and Control

  • Centralized admin dashboard
  • Group-level permissions
  • Team-wide scheduling rules
  • Resource allocation tools
  • Usage analytics and insights

Compliance and Data Management

  • Detailed audit logging
  • Data deletion API access
  • Security review tools
  • Communications archiving
  • Compliance documentation

Support Experience

  • Phone support + 24/7 email and chat support
  • Dedicated account manager
  • Onboarding and implementation
  • Data Deletion API that helps to manage privacy compliance by automatically removing personal information (PII) for both meeting participants and users across the entire platform.
  • Regular check-ins
  • Security and legal reviews

Calendly Enterprise integrations

You might be interested to know that Calendly integrates with 80+ tools. Here's a quick look:

Video & Communication Platforms

  • Google Meet
  • Microsoft Teams
  • Zoom
  • WebEx
  • GoToMeeting
  • Slack

Payment Integration

  • Stripe
  • PayPal

Marketing & Automation Tools

  • Zapier Connection - Opens up possibilities with 700+ app integrations through automated workflows
  • Webhook Support - Enables custom integrations with any system supporting webhooks
  • Mailchimp Integration - Syncs scheduling data with email marketing campaigns
  • Marketo Connection - Automatically updates marketing automation workflows with event data
  • HubSpot Integration - Connects scheduling directly with marketing and sales automation
  • Pardot Integration - Links scheduling data with Salesforce's marketing automation platform

CRM Systems

  • Salesforce Integration
  • Microsoft Dynamics 365
  • HubSpot CRM

Calendar Platforms

  • Google Calendar
  • Outlook
  • Office 365
  • Exchange

Advanced Routing Options

  • HubSpot Assignment Routing
  • Salesforce Assignment Routing
  • Marketing Form Integration - Connects with HubSpot, Pardot, and Marketo forms for automated routing

Analytics & Email

  • Google Analytics Integration - Tracks scheduling patterns and conversion data
  • Meta Pixel Integration - Enables Facebook advertising tracking and optimization
  • Gmail Integration - Supports advanced email workflow automation
  • Outlook Email Integration - Enables Microsoft email workflow automation

Enterprise Management

  • Organization-wide Integrations - Centrally manages all integration settings across the organization
  • Power Automate Support - Enables custom Microsoft workflow automation

How Enterprise Compares to Other Calendly Plans

Understanding the differences between Enterprise and other Calendly tiers is crucial for making an informed decision about your organization's scheduling solution. Let's break down how each plan stacks up against Enterprise, examining everything from core features to advanced capabilities.

Pricing Structure

  • Calendly Free: Always free, best for individuals starting out
  • Standard: $10/user/month, suited for professionals and small teams
  • Teams: $16/user/month, designed for growing teams
  • Enterprise: Starting at $15k/year (minimum 30 users), built for large organizations

Feature Comparison Breakdown

Features Free
($0)
Standard
($10/month/user)
Teams
($16/month/user)
Enterprise
(From 15k)
Calendar connections 1 2 6 6
Meeting platforms (Google Meet, Teams, Zoom, etc)
Website embedding
Payment collection (Stripe/PayPal) -
One-on-One events
Group events -
Collective scheduling - -
Round-robin scheduling - -
Event notifications & reminders
Automated workflows -
Marketing integrations (Mailchimp, HubSpot) -
Analytics tracking (Google Analytics, Meta Pixel) -
Routing forms - -
Marketing forms routing (HubSpot, Pardot, Marketo) - -
Hide Zeeg branding - -
Custom email designs -
SMTP integration -
Create organization - - Unlimited
Create teams - - Unlimited
Single Sign-On (SSO) - - -
SCIM provisioning - - -
Advanced integrations - -

Core Scheduling Capabilities

  • Event Types: While all plans offer event creation, Enterprise provides unlimited event types with advanced customization options
  • Calendar Connections: Free plan limited to 1 calendar, while Standard through Enterprise support 6 calendar connections per user
  • Group Events: Available in Standard and above, but Enterprise adds advanced scheduling rules and automation
  • Meeting Types: Enterprise supports all meeting types (one-on-one, group, collective, round-robin) with additional customization options

Security and control

Moving beyond the basic security features of the Free and Standard plans, the Enterprise tier introduces several robust security measures. At its core, SAML Single Sign-On (SSO) handles authentication needs, while SCIM user provisioning streamlines the management of multiple users across systems. Organizations can also maintain their professional image through custom domain control, integrating their brand throughout the scheduling experience. When it comes to monitoring and compliance, the Enterprise plan incorporates industry-standard features such as audit logs and activity tracking, alongside a data deletion API for data management. While these security features work together cohesively, they represent what you'd typically expect from enterprise-grade software.

User management

Building on the foundation of basic user controls, the Enterprise plan addresses the complexities of large-scale user management. This starts with group-level permissions that accommodate different organizational structures, flowing into scheduling rules that help coordinate team activities. To tie everything together, a centralized admin dashboard provides oversight of scheduling operations – though the learning curve might take some time to master. While the tools are comprehensive, they require proper setup and maintenance to deliver their full value.

Support structure

The support system shifts from basic assistance to a more comprehensive model in the Enterprise tier. Instead of relying on community forums or standard chat support, organizations work with dedicated account partners and have access to priority support channels. This includes implementation guidance, onboarding assistance, and regular check-ins to discuss platform usage. While this level of support can help organizations maximize their investment, the value largely depends on how actively teams engage with these resources and implement the suggested best practices.

Integrations capabilities with other tools

When it comes to connecting with other business tools, the Enterprise plan expands the integration possibilities significantly. Beyond basic calendar connections, it offers standard enterprise integrations with platforms like Salesforce and Microsoft Dynamics 365. Organizations can also develop custom solutions through API access, though this requires technical expertise to implement effectively. The workflow automation features allow for sophisticated process creation, but like many enterprise tools, the real value emerges through careful planning and proper configuration. While the integration framework is extensive, organizations should assess whether these capabilities align with their actual integration needs and technical resources.

Key differences

What truly sets Enterprise apart is its comprehensive approach to scheduling infrastructure:

  1. Scale and Control: Enterprise provides the tools needed to manage scheduling across large organizations while maintaining security and compliance.
  2. Advanced Automation: While other plans offer basic automation, Enterprise enables complex workflow creation and management.
  3. Custom Solutions: Enterprise customers receive tailored solutions for their specific needs, unlike the one-size-fits-all approach of lower tiers.
  4. Premium Support: The dedicated support structure ensures organizations can maximize their investment and quickly resolve any issues.
  5. Security Compliance: Enterprise-grade security features help organizations meet strict compliance requirements while maintaining efficient scheduling processes.

Where Calendly Enterprise falls short

While Calendly Enterprise offers great scheduling capabilities, there's a few things in this plan that might make you cancel your Calendly subscription, not want to upgrade to Calendly Enterprise, or simply for another enterprise-grade alternative.

Data privacy and GDPR considerations

One significant concern for international organizations is Calendly's data handling infrastructure. While the company commits to data protection and privacy compliance, their server infrastructure is primarily based in the United States. This setup can present challenges for European organizations or businesses dealing with EU customers who must strictly adhere to GDPR requirements. Though Calendly has implemented various compliance measures, organizations with stringent data residency requirements should carefully evaluate whether these measures fully align with their compliance needs.

If you're looking for GDPR compliant alternatives to Calendly, you might want to have a look at Zeeg.

Calendar integration limitations

A notable technical limitation is Calendly's inability to integrate with Apple Calendar. While existing connections may continue to function, new users or those attempting to establish new connections with Apple Calendar might encounter difficulties. This can be particularly problematic for organizations where many team members rely on Apple's ecosystem for their calendar management.

Investment considerations

The pricing structure of Calendly Enterprise represents a substantial investment, especially for growing organizations:

  • The $15,000 annual minimum commitment can be steep for mid-sized companies
  • The requirement of 30+ users might not align with smaller enterprise teams
  • Per-user costs (approximately $42/month) run higher than many competing scheduling solutions
  • The annual billing requirement affects cash flow flexibility

While volume discounts are available, the initial price point may be prohibitive for organizations that don't need all the enterprise features but require the platform for a large team. This can be particularly challenging for:

  • Non-profits and educational institutions
  • Growing businesses approaching enterprise scale
  • Organizations with seasonal scaling needs
  • Teams with mixed scheduling requirements

Customization and flexibility tradeoffs

Despite its robust feature set, some organizations might find limitations in:

  • The depth of customization available for complex scheduling workflows
  • The rigidity of certain enterprise-level settings
  • The ability to create highly specialized scheduling rules
  • Options for localized data storage preferences

Zeeg: A fully compliant alternative for modern businesses

Data privacy done right

Unlike Calendly's US infrastructure, Zeeg maintains data centers in the EU, ensuring true GDPR compliance from the ground up. This gives you complete control over where your data lives - a crucial feature for businesses with international operations.

Seamless Apple Calendar integration

While Calendly doesn’t support new Apple Calendar connections, Zeeg offers full integration capabilities, besides Google Calendar, Outlook, Microsoft, Zoom, Teams, Hubspot, Zapier, and many more. But, back to the main point - your team can easily connect and sync with Apple Calendar, making it a perfect fit for organizations using Apple's ecosystem.

Enterprise features at custom pricing

Zeeg's Enterprise plan comes with everything you need, priced according to your business requirements:

  • Unlimited team creation and organization
  • Advanced business integrations (Zapier, HubSpot, Google Analytics)
  • Single Sign-On (SSO) with Azure AD
  • User provisioning with SCIM
  • Premium support
  • Round-robin scheduling
  • Custom branding options
  • Flexible event routing based on custom logic
  • Multiple hosts with one invite functionality
  • Collective scheduling capabilities
  • Organize users by department, location, or job role
  • Advanced routing forms to direct appointments to the right person
  • Customizable workflow automation with follow-up and reminder system

Plus, you won't face the steep $15,000 annual minimum that Calendly requires. Zeeg works with your budget to deliver enterprise-grade scheduling that makes sense for your business.

Frequently Asked Questions

What's the minimum commitment for Enterprise?

Enterprise plans require a minimum of 30 users and start at $15,000 per year.

Can we customize the Enterprise package?

Yes, Calendly offers flexibility in feature bundling and pricing for Enterprise customers.

How long is the implementation process?

Implementation typically takes 2-4 weeks, depending on your organization's size and requirements.

Is data migration support included?

Yes, Enterprise customers receive dedicated migration and implementation support.

Can we integrate with custom systems?

Yes, Enterprise plans support custom integrations through APIs and specialized connections.

Conclusion

Calendly Enterprise represents a significant step up from basic scheduling tools, offering a robust solution for large organizations with complex scheduling needs. While the investment is substantial, the combination of advanced features, security measures, and dedicated support can make it a valuable addition to your business technology stack.

The key is to evaluate your organization's specific needs against the features and capabilities offered. Consider factors like team size, security requirements, integration needs, and budget constraints. Take advantage of demos and trials when available, and don't hesitate to negotiate terms that better suit your organization's needs.

Before making your final decision between Calendly Enterprise or other options

When evaluating Calendly Enterprise, you'll want to weigh both its strengths and key considerations carefully. On the positive side, the platform offers a comprehensive feature set that covers most enterprise scheduling needs. Its robust security measures help protect your organization's data, while extensive integration options let you connect with your existing tech stack seamlessly. The strong support system ensures you have help when needed, and their proven enterprise track record demonstrates reliability for large-scale operations.

However, there are several important factors to consider before making your decision. Calendly might expensive when compared to other tools, which might strain your budget, especially with their minimum user requirement. Teams should also be prepared for a learning curve when implementing some of the advanced features. Additionally, the integration complexity might require dedicated IT resources to set up and maintain properly.

As an alternative worth considering, Zeeg offers similar enterprise-level features with some key advantages: true GDPR compliance with both EU and US data centers, seamless integrations (including Apple), and custom pricing without the steep $15,000 annual minimum. This flexibility, combined with comprehensive enterprise features, makes Zeeg a compelling option for organizations seeking a more adaptable solution.