Calendly
Gladly
| Feature | Calendly | Gladly |
|---|---|---|
| Pricing | Free / from $12/mo | From $180/mo |
| Free Plan | ✓ Yes | ✗ No |
| Rating | 4.6 / 5 | 4.5 / 5 |
| Best For | sales-teams, recruiters, consultants, freelancers, customer-success | ecommerce-brands, luxury-retail, enterprise-support, customer-obsessed-teams |
| Founded | 2013 | 2014 |
| Scheduling | ✓ | ✗ |
| Calendar Sync | ✓ | ✗ |
| Routing | ✓ | ✗ |
| Workflows | ✓ | ✗ |
| Team Pages | ✓ | ✗ |
| Analytics | ✓ | ✗ |
| Integrations | ✓ | ✗ |
| Unified Conversation | ✗ | ✓ |
| Omnichannel Inbox | ✗ | ✓ |
| Voice Support | ✗ | ✓ |
| Self Service | ✗ | ✓ |
| Customer Timeline | ✗ | ✓ |
| Task Management | ✗ | ✓ |
✓ Calendly Pros
- Eliminates scheduling friction completely
- Integrates with all major calendars
- Routing forms for lead qualification
- Team scheduling with round-robin
✗ Calendly Cons
- Free plan limited to one event type
- Can feel impersonal to some recipients
- Advanced routing only on higher plans
✓ Gladly Pros
- Single conversation thread per customer
- Excellent omnichannel support
- Built-in voice and messaging
- Customer-first approach
✗ Gladly Cons
- Very expensive per agent
- Enterprise-focused
- Smaller marketplace of integrations
The Verdict
Calendly is built for sales teams and recruiters, with a focus on scheduling and calendar-sync. Gladly targets ecommerce brands and luxury retail and leads with unified-conversation and omnichannel-inbox.
On pricing, Calendly is the clear winner for budget-conscious users — starting at $12/mo compared to $180/mo for Gladly. That $168/mo difference adds up quickly for growing teams.
Calendly has a free plan, which gives it a meaningful edge for individuals and small teams exploring their options. Gladly requires a paid subscription from day one.
Feature-wise, Calendly offers broader built-in capabilities (7 features vs 6), while Gladly takes a more focused approach — which can mean a simpler, faster onboarding experience.
This is a genuinely close comparison. If you can, sign up for both free trials (where available) and run a one-week test with your actual team tasks before deciding.
