Prerequisites

• Calendly admin / owner access (you need access to event-type definitions and team settings).
• A self-hosted Cal.com instance — see /calendly/ for the 20-minute docker-compose recipe and ~$5-10/mo VPS sizing.
• Google Workspace or Microsoft 365 admin consent for OAuth (so users can re-connect their calendars to Cal.com).
• A domain you control for Cal.com — booking pages live at `cal.your-domain.com/yourname/event-type` rather than `calendly.com/yourname/...`.
• An inventory of every place your Calendly link is published (email signature, website CTAs, CRM, lead-magnet pages) — these all need updating during the cutover.

Step 1 — Export from Calendly

1. Export past bookings (for archival reference)

   Calendly → Scheduled Events → Export. Pull a CSV of past bookings for record-keeping. This is purely archival — Cal.com does not import past bookings, and most teams don't need them in the new tool.

2. Document each event type

   For each Calendly event type (15-min intro, 30-min sales call, etc.), open the event-type config and screenshot or document: name, slug, duration, calendar(s) checked, custom questions, redirect URL, conditional logic, Zapier/webhook integrations, reminders, and round-robin settings. This is your spec for the Cal.com rebuild.

3. Document team / round-robin pools

   If you use Calendly Teams, list each team's members, their availability rules, and the round-robin event types they're part of. Cal.com Teams replicates this concept under Teams → Members → Round Robin.

4. Audit external embeds and integrations

   Inventory: every page that embeds the Calendly inline widget, every Zapier zap that fires on a Calendly booking, every Salesforce/HubSpot integration. Each gets re-pointed at Cal.com post-migration.

Step 2 — Import into Cal.com

5. Stand up Cal.com and create user accounts

   Run the docker-compose. Visit your Cal.com URL and click Sign Up — the first signup becomes admin. Create accounts for each team member (or invite via email).

6. Connect calendars

   Each user: Cal.com → Settings → Apps → Google Calendar / Outlook. The OAuth flow reuses the same consent your team has already given to Calendly. Cal.com will read free/busy from the connected calendar and write new bookings back.

7. Recreate event types one by one

   Cal.com → Event Types → New. For each Calendly event type, fill in: title, URL slug (preserve the Calendly slug like `30min` to keep link patterns familiar), duration, location (Google Meet / Zoom / phone — connect the integration first if needed), description, custom questions, redirect URL on confirmation. Save. Repeat per event type.

8. Set up team event types and round-robin

   Cal.com → Teams → Create Team. Add members. Then Team → Event Types → New: select Round Robin or Collective. For round-robin, list members and assign weights. The model is similar enough to Calendly's that the rebuild is a click-through, not a rebuild from concepts.

9. Configure workflows (reminders / follow-ups)

   Cal.com → Workflows → New Workflow. Trigger: 24h before event, on booking, on cancellation. Action: send email or SMS. Recreate each Calendly Workflow as a Cal.com Workflow — the trigger/action shapes match closely.

10. Update embeds and links

    Replace `https://calendly.com/yourname/30min` with `https://cal.your-domain.com/yourname/30min` everywhere it appears. Cal.com supports an inline embed snippet (Cal.com → Embed → Inline) that is a drop-in replacement for Calendly's `<script src='https://assets.calendly.com/...'></script>`.

11. Forward Calendly bookings during overlap window

    Calendly does not have a native 'redirect' but you can replace each event type's title and description with 'We've moved! Book at cal.your-domain.com/yourname/30min'. Existing booked events continue on Calendly until they happen; new ones go to Cal.com.

Field / concept mapping

Downtime estimate

Zero downtime if you run a 2-week overlap. Calendly stays live with redirected event-type descriptions; Cal.com handles new bookings. Hard cutover (single-day): plan 4-6 hours to recreate event types for one user, longer for team-heavy setups. Schedule the cutover for a low-traffic day so a missed event-type slot doesn't lose a real meeting.

Common gotchas

• Calendly does not have a structured event-type export. Don't waste time looking — go straight to manual recreation or scripting against the Calendly API (which exists for read but is rate-limited).
• Cal.com's default DB is SQLite — fine for personal use, but for teams switch to Postgres at install time (`DATABASE_URL=postgres://...`) before creating any data.
• Round-robin weights in Cal.com are per-team-event-type, not per-user globally. If a user is on multiple teams, set weights per team.
• Calendly's group event type (multiple attendees per slot) maps to Cal.com's Group event type — same concept, but the display UI is slightly different. Test from a guest's perspective before going live.
• Booking page styling: Calendly auto-pulls profile photos and brand colors. Cal.com requires a manual upload of the avatar and a CSS theme for branding.

Rollback plan

Calendly is unaffected during the migration since the data flow is one-way (manual recreate, not destructive). If Cal.com doesn't fit, point published links back to Calendly and you've lost only the time spent. Keep the Calendly account paid for 30 days post-cutover; the booking page returning a 404 mid-migration is the worst-case for the funnel and is preventable by keeping both live.