Hey there @Jennifer87832 - great question! Firstly, check out our New User Guide - it’ll def prove helpful as you get used to the platform!

In order to allow two invitees to book per time slot you’ll want to set up a Group Event Type - this allows one host > many invitees to meet simultaneously! 

You will need to upgrade from the free plan in order to do this, yes!

(Note: you absolutely do not have to pay per invitee/time slot! “Paid seats” are for additional team members that you add as users to your Calendly account - there is not a limit to the number of invitees that you can allow to book with you per plan tier! You will simply pay for one paid seat - your own - unless you have a team member you’d like to add at some point. This will be $10/month if you pay annually or $12/month if you pay monthly on our Standard plan.)

You’ll want our Standard plan at least. You can read more about our plans, pricing and features on our Pricing Page! Note: an annual subscription will result in a 20% discount for all paid plans!

Standard
Our Standard plan is:

• $10/user/month (billed annually)
• $12/user/month (billed monthly)

For small teams or individuals with more sophisticated scheduling needs
Standard features include all Free features, plus

• Group and collective event types
• Multiple calendars for availability and scheduling
• Unlimited one-on-one event types
• Reminders, reconfirmation requests and other workflows
• Customizable branding and logos on your website
• Hubspot, Paypal, Stripe, and 100s of integrations
• Live chat support

Teams
Our Teams plan is:

• $16/user/month (billed annually)
• $20/user/month (billed monthly)

For the admin that wants more, including Salesforce and Round Robin.
Teams features include Standard features, plus

• Connect to Salesforce to flow meeting data into the CRM
• Round Robin events
• Route leads with Hubspot, Marketo, or Pardot forms
• Lock and sync admin-managed event templates

I hope this helps! You might find this article useful, too!