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Schedulingcalendly.com

Calendly + Pitchsite Integration

Embed a Calendly booking link in every proposal

Calendly is the scheduling automation platform used by millions of professionals to eliminate back-and-forth meeting coordination. Adding a Calendly link to your Pitchsite proposals lets prospects book a discovery call or presentation while they're actively engaged — turning proposal reads into scheduled conversations.

How to use Calendly + Pitchsite

A step-by-step look at how Calendly and Pitchsite work together.

1

Connect your Calendly account

Authenticate Pitchsite with Calendly via OAuth. Your event types (discovery call, proposal walk-through, kick-off) sync to Pitchsite.

2

Embed your Calendly link in proposals

Add a "Book a call" section to your Pitchsite proposal with your Calendly scheduling widget embedded inline — prospects book without leaving the proposal page.

3

Route to the right event type by proposal type

New prospect proposals show your "Discovery Call" Calendly event; signed proposals show your "Kick-off Call" event — the right conversation at the right time.

4

Trigger Pitchsite follow-up on booking

When a prospect books via the Calendly embed on your proposal, Pitchsite logs the booking as a deal activity and sends a personalised confirmation message.

5

Auto-send proposals after discovery calls

Configure Calendly to trigger a Pitchsite proposal creation after a discovery call is completed — the proposal goes out within 24 hours of the call, automatically.

Use cases

Real ways agencies use Calendly and Pitchsite together.

Convert proposal reads to booked calls

Prospects who read a proposal are 5× more likely to book if given the option in the moment. Embedded Calendly in Pitchsite captures that intent before it evaporates.

Post-signature kick-off scheduling

The moment a proposal is signed, Calendly makes it easy to book the kick-off call without a separate email thread — keeping momentum from "yes" to "started" at maximum speed.

Automated post-call proposal dispatch

Discovery call ends → Calendly marks it complete → Pitchsite auto-generates the proposal → sent within the hour. A sales process that runs itself.

Re-engagement for cold proposals

Proposals that go quiet for 7 days automatically get a follow-up email with a Calendly link: "Happy to walk you through it — book 15 minutes here." Reactivate cold deals with minimal effort.

Key benefits

Why agencies connect Calendly to Pitchsite.

  • Calendly booking widget embedded inline in proposals — no external redirect
  • Route to different event types (discovery, kick-off, walk-through) based on proposal stage
  • Proposal bookings logged as deal activities automatically
  • Auto-generate proposals after Calendly discovery calls are completed
  • Works with Calendly Free, Standard, Teams, and Enterprise plans
  • Eliminates scheduling back-and-forth at the highest-interest moment
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Pitchsite

Calendly + Pitchsite

Embed a Calendly booking link in every proposal

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Frequently asked questions

Does Calendly routing logic work with embedded proposals?

Yes. Calendly's routing forms can qualify prospects before they book, sending them to the right team member based on their answers — all within the embedded proposal experience.

Can I use Calendly team scheduling in proposals?

Yes. Embed a Calendly team event type that round-robins across your sales team — prospects get the next available rep, proposals get addressed faster.

Can I customise the Calendly event description to reference the proposal?

Yes. Calendly event descriptions can include the proposal name and a link, so whoever takes the meeting has full context before the call.

What happens if a prospect books but doesn't attend?

Calendly sends automatic reminders and follow-up emails. You can also configure Pitchsite to send a re-engagement message to no-show prospects from a scheduled call.

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