sales-skills/sales-calendly

Calendly Platform Help

Step 1 — Gather context

If references/learnings.md exists, read it first for accumulated platform knowledge.

Ask the user:

1. What area of Calendly do you need help with?

   • A) Booking pages & event types — setup, customization, branding
   • B) Round-robin & team scheduling — routing, collective events
   • C) Routing forms — lead qualification before booking
   • D) API & webhooks — building integrations, syncing data
   • E) Workflows — automated reminders, follow-ups, notifications
   • F) Embeds — inline, popup widget, or popup text in your site/app
   • G) Payments — Stripe/PayPal collection on booking
   • H) Integrations — Salesforce, HubSpot, Zapier, etc.
   • I) Choosing Calendly vs Cal.com vs other tools
   • J) Something else

2. What plan are you on?

   • A) Free (1 event type, 1 calendar)
   • B) Standard ($10-12/seat/mo)
   • C) Teams ($16-20/seat/mo)
   • D) Enterprise
   • E) Not sure yet / evaluating

If the user's request already provides most of this context, skip directly to Step 2. Lead with your best-effort answer using reasonable assumptions (stated explicitly), then ask only the most critical 1-2 clarifying questions at the end.

Step 2 — Route or answer directly

If the request maps to a specialized skill, route:

• General scheduling strategy → "This is a scheduling strategy question — run: /sales-meeting-scheduler {user's question}"
• CRM integration patterns → "This is a tool integration question — run: /sales-integration {user's question}"
• No-show recovery or reminder design → "This is a scheduling optimization question — run: /sales-meeting-scheduler {user's question}"
• Comparing Calendly vs Cal.com → "For head-to-head comparison — run: /sales-meeting-scheduler compare Calendly vs Cal.com"

If the question is Calendly-specific, continue to Step 3.

Step 3 — Calendly platform reference

Read references/platform-guide.md for the full platform reference — capabilities, pricing, data model, integration recipes, code examples.

Answer the user's question using only the relevant section. Don't dump the full reference.

For API or webhook questions, also read references/calendly-api-reference.md for endpoint details, JSON shapes, and code examples.

Step 4 — Actionable guidance

Focus on the user's specific situation.

• Free plan users: Note the 1-event-type limit — suggest Standard if they need multiple event types or workflows
• API builders: Calendly now has a Scheduling API (POST /invitees) that creates bookings programmatically — paid plan required. The API can also create/update 1:1 event types and update availability schedules. Embeds and scheduling links are still useful (and the only path on Free).
• Team admins: Round-robin and routing forms require Teams plan ($16/seat/mo)
• Migration: Cal.com offers a 1-click Calendly import tool if they're evaluating switching

If you discover a gotcha, workaround, or tip not covered in references/learnings.md, append it there.

Gotchas

Best-effort from research — review these, especially items about plan-gated features and integration gotchas that may be outdated.

• Free plan = 1 event type only. No group events, no workflows, no custom branding. Standard ($10/mo) unlocks unlimited event types.
• API CAN create bookings (since the 2025 Scheduling API). POST /invitees (Create Event Invitee) books a meeting programmatically — paid plan required, PAT or OAuth. The API can also create/update 1:1 event types and update availability. Scheduling links/embeds remain the Free-plan path.
• Webhooks require a paid plan. Free plan has no webhook access. Standard unlocks invitee.created and invitee.canceled.
• Rate limits vary by plan. Roughly 60 req/min on Free/Standard/Teams, 120 req/min on Enterprise (exact numbers not cleanly re-verifiable on the live docs — treat as approximate). HTTP 429 includes a Retry-After header; honor it.
• Routing forms require Teams plan. Lead qualification routing is not available on Standard.
• Round-robin requires Teams plan. Equal distribution and availability-optimized routing both need Teams ($16/seat/mo).
• Salesforce integration requires Teams plan. HubSpot is available on Standard.
• No Apple Calendar support. Only Google Calendar, Outlook/Office 365, and Exchange are supported natively.

Related skills

• /sales-meeting-scheduler — Scheduling strategy across all tools (booking pages, round-robin, no-show reduction, meeting page CRO). Install: npx skills add sales-skills/sales --skill sales-meeting-scheduler -a claude-code
• /sales-calcom — Cal.com platform help — open-source alternative with self-hosting and more generous free tier. Install: npx skills add sales-skills/sales --skill sales-calcom -a claude-code
• /sales-reclaim — Reclaim.ai platform help — AI calendar automation. Install: npx skills add sales-skills/sales --skill sales-reclaim -a claude-code
• /sales-integration — Tool integration patterns (CRM sync, webhooks, API pipelines). Install: npx skills add sales-skills/sales --skill sales-integration -a claude-code
• /sales-do — Not sure which skill to use? The router matches any sales objective to the right skill. Install: npx skills add sales-skills/sales --skill sales-do -a claude-code

Examples

Example 1 — "I set up Calendly but prospects in Europe keep seeing the wrong meeting times" → Read platform guide timezone section → Check if the user has set their event type timezone to "Automatically detect" or locked it → Explain that Calendly converts times but the event type's timezone setting matters → Note Apple Calendar incompatibility if relevant

Example 2 — "How do I sync Calendly bookings to my CRM via the API?" → Read API reference → Show webhook subscription setup (POST /webhook_subscriptions for invitee.created) → Provide Python listener example that parses invitee data and POSTs to CRM → Note: requires paid plan for webhooks

Example 3 — "Should I stay on Calendly or switch to Cal.com? I'm a solopreneur." → Compare: Cal.com free has unlimited event types + CRM sync; Calendly free has 1 event type. If user needs multiple booking types or API access on free tier, Cal.com wins. If user values simplicity and brand recognition, Calendly Standard at $10/mo is solid. Route to /sales-meeting-scheduler for full comparison.

Troubleshooting

Timezone mismatch — invitees see wrong times

• Check event type settings → Availability → ensure timezone is set to "Automatically detect invitee's timezone" (not locked to your zone)
• If using embeds, verify the embed snippet doesn't override timezone with a hardcoded value
• Confirm the connected calendar's timezone matches Calendly account timezone

Double bookings or calendar conflicts

• Check connected calendars: Calendly only blocks times from connected calendars. If a calendar isn't connected, those events won't show as busy.
• Verify "Check for conflicts" is enabled for all relevant calendars in Settings → Calendar Connections
• Buffer time between events: set minimum scheduling notice and buffer time in event type settings

Webhook not firing

• Confirm you're on a paid plan (webhooks not available on Free)
• Check webhook subscription is active: GET /webhook_subscriptions and verify state: "active"
• Verify the webhook URL is HTTPS and publicly accessible — Calendly won't POST to HTTP or localhost
• Check the signing secret: validate Calendly-Webhook-Signature header using HMAC-SHA256 with your signing key