Calendly vs Chili Piper

Calendly9.3Visit Chili Piper8.3Visit

Higher score Calendly #1 in Sales Appointment Scheduling Software 9.3/10 Free plan · 14-day trial Free planFree trial✓ 1 of 5 features Visit Calendly

vs

Chili Piper #5 in Sales Appointment Scheduling Software 8.3/10 Paid ✓ 1 of 5 features Visit Chili Piper

• Calendly fits best

  Sales teams coordinating and routing meetings

• Chili Piper fits best

  Revenue teams needing advanced lead routing

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Side by side

Feature	Calendly 9.3/10 Visit ↗	Chili Piper 8.3/10 Visit ↗
At a glance
Editor score	9.3	8.3
Ranking	#1 in Sales Appointment Scheduling Software	#5 in Sales Appointment Scheduling Software
Best for	Sales teams coordinating and routing meetings	Revenue teams needing advanced lead routing
Pricing model	Free plan + paid	Paid
Starting price	$10/seat/mo (best)	$12/user/mo
Free plan	✓ (best)	—
Free trial	14 days	—
Deployment	Cloud, Mobile, Browser extension	Cloud, Browser extension
Platforms	Web, iOS, Android, Chrome extension	Web, Chrome extension
Support	Community, Docs · 24/7	Email, Tickets, Live chat, Community, Docs
Compliance	SOC 2, ISO 27001, PCI DSS, SSO/SAML, 2FA	SOC 2, ISO 27001, GDPR, SSO/SAML
Integrations	150+ integrations	16 integrations
Built for	Solo, Small business, Mid-market, Enterprise	Mid-market, Enterprise
Features Calendly 1/5 · Chili Piper 1/5
Qualification forms	Not checked yet	Not checked yet
Round-robin routing	Not checked yet	Not checked yet
Lead routing	Not checked yet	Not checked yet
CRM integrations	Not checked yet	Not checked yet
Automated reminders	✓	✓
Specs
Meeting types	Not checked yet	Not checked yet
Included team seats	Not checked yet	Not checked yet
Our review
Pros	Free plan includes a customizable booking page and one-on-one scheduling Teams adds round-robin scheduling, lead routing, and Salesforce integration Connects calendars, video conferencing, CRM, and payment tools	Offers round-robin, group, personal, and ownership-based booking links Syncs Google Calendar and Office 365 two ways, with email and SMS reminders Connects CRM write-back and Salesforce with routing and meeting analytics
Cons	Free plan is limited to one event type and one calendar connection Round-robin and lead routing require the Teams plan Enterprise features and dedicated support are reserved for Enterprise	No free plan; the $12 monthly option excludes AI credits and routing Routing & Scheduling starts at $1,250 per month on annual billing AI web experiences start at $3,500 per month on annual billing
Our verdict	Calendly lets people publish booking pages, connect calendars, set availability, and let invitees schedule without back-and-forth email. It supports one-on-one, group, collective, multi-host, and round-robin meetings, making it suitable… Read the review →	Chili Piper combines appointment scheduling with lead qualification and routing for revenue teams, particularly mid-market and enterprise organizations that need to get prospects to the right people. Booking links support personal, group,… Read the review →

Strengths and trade-offs

• Calendly — where it wins

  • Free plan includes a customizable booking page and one-on-one scheduling
  • Teams adds round-robin scheduling, lead routing, and Salesforce integration
  • Connects calendars, video conferencing, CRM, and payment tools

  Where it doesn't

  • Free plan is limited to one event type and one calendar connection
  • Round-robin and lead routing require the Teams plan
  • Enterprise features and dedicated support are reserved for Enterprise

• Chili Piper — where it wins

  • Offers round-robin, group, personal, and ownership-based booking links
  • Syncs Google Calendar and Office 365 two ways, with email and SMS reminders
  • Connects CRM write-back and Salesforce with routing and meeting analytics

  Where it doesn't

  • No free plan; the $12 monthly option excludes AI credits and routing
  • Routing & Scheduling starts at $1,250 per month on annual billing
  • AI web experiences start at $3,500 per month on annual billing

• Calendly9.3/10 · Free plan · 14-day trial

  A flexible scheduler for solo users and sales teams, with routing and CRM integrations.

  Visit CalendlyFull verdict →
• Chili Piper8.3/10 · Paid

  Combines meeting booking with lead qualification and routing, but advanced tiers are costly.

  Visit Chili PiperFull verdict →