Hey there @FieldSched - thanks sooo much for the very thorough overview of your use case, here! It’s literally my favorite thing, seeing all the info I need to best help YOU! So this is fantastic! 
FIRST - check out our Company Admin Guide - it goes over tons of helpful stuff about running teams within Calendly. Our New User Guide will help as you learn the ropes as well!
You can do almost everything you are hoping to do here natively in Calendly. I am gonna go ahead and respond in the same list-fashion and then add more details below, as I go. Let me know if anything is tricky, doesn’t make sense, or is just plain unhelpful - and we will keep talking to sort whatever it is out! 
- For bullets 1-3, this is easy. Make sure to add each contractor as a user to your Calendly organization. It might be be best to set up a different Team Page for each geo location to keep things organized internally as well!
- Yes - you can allow invitees to book pretty easily based on geo location using some of our native tools - and you were on right track yourself, already! Routing forms let you request information such as industry, company size, specific interests, etc. from website visitors and automatically direct them to a specific scheduling or web page based on their responses. It's great for screening and qualifying sales leads on a website or matching clients or students to the booking page of the right subject-matter expert based on their interests, program, or other criteria. You can read more about setting up routing forms, here! I would suggest setting up routing that asks invitees what geo location they will be booking in (and provides either a dropdown of options to choose from or radio buttons, same). Then, use logic to route them to the appropriate event types.
- You will want to create at least one event type for each geo location for the purpose of routing. You can either use Round Robin Event Types and assign all contractors in the geo location to a single Round Robin Event Type, or, create “one-on-one” event types on each team page, one for each contractor. You cannot create TRUE one-on-one event types on a team page but you can use Round Robin or Collective Event Types with a single host assigned to each to work around this - read more about how here.
- There is not a way to share your booking page (where availability appears publicly) on your website without it also being a live booking form at this time. A workaround might be using a third party tool to pull availability somehow and embed it that way. You might also simply set up an infographic that shows different options on your website that is not affiliated with your Calendly booking page/account. I wish I had more to offer here - so sorry!
- Yes! We have integrations with both Stripe and PayPal. You can connect your Stripe or PayPal account to Calendly to collect payments when your invitees schedule with you. If you don't use these services, you could add a custom link to your confirmation page that leads to your preferred payment provider. You could also customize your invitee notification emails to include that link! However, there is not a way at this time to allow for the initial booking on an event type to be free (because they already paid) and then charge for bookings after that. To do this, you’d need to create two event types for each geo location (at least - if you are using a single Round Robin for each location as suggested - if you create one event type for each host you’d need two for each host to do this) - one that does not collect payments and one that does. You can clone the one that does not collect payments, make it secret and add payment collections - then add another routing question, “Is this your first booking with us?” and route invitees to either the free or paid event based on that. You could also redirect invitees from the free event to the appropriate paid event, encouraging them to book again right away.
- There is currently no support for uploading attachments when booking or within Calendly. I’m sorry!
I hope this helps!
You might also want to check out the following articles we’ve written in community:
...and make sure to use our “search” feature to unlock lots more. I’ll be here if you need me! 
Edit note: added a link to “redirect” so you’d have that info, too - this is under the second-to-last bullet about payments.
Super-helpful, appreciate the setup guidance. We’ll go through the links thoroughly & follow up as we have more questions!
Super-helpful, appreciate the setup guidance. We’ll go through the links thoroughly & follow up as we have more questions!
Wonderful - sounds perfect!
I did also mean to tell you to look into these things/features/automations for your team as you setup:
Let us know how it all goes!
Hi Kelsi! Your recommended Calendly routing form/team page/round robin approach sounds ideal so far.
A few quick followup questions:
1 - annual team pricing - we can reassign seats at no charge as actual human team members come/go, yes?
2 - best way to keep contractor names somewhat private - for example, first name + last initial or just first name?
employee poaching is an issue in our industry.
We’d rather not make it easy for a competitor to essentially build a list of our entire contractor network just by walking through all the routing form branches 
3 - are team members (aka contractors) able to see each other’s details and freely contact each other within the Calendly environment?
if so, is there a way to limit this?
4 - In certain geos, we also offer in-person “meetup” type groups with a max capacity of, say 10 attendees - versus the 1:1 scenario I originally outlined.
How would you suggest we tweak this approach to accommodate?
I’m thinking a different event-type, and the option to choose the in-person group upstream in the routing flow?
Any other nuances to consider on that scenario?
@Kelsi at Calendly oops, forgot to tag you above!
Hey @FieldSched - great questions, and I am definitely ready to answer them all! FYI - you don’t need to worry about directly tagging me too much. 
I am notified every time a user in community responds to me via internal tools we have to make sure we are on top of things, so that you don’t ever have to wait too long for our masterful, super engaging and all-around-welllll-appreciated help! Right? 
Right!
Okay - here goes!
- Check out our Pricing Page for an overview of annual vs. monthly pricing, pricing per seat/user and the different plans we have to offer. To answer this question, yes! You pay for seats, not users. You can always remove a user and add a new one to fill the seat they left vacant rather than removing the user and seat just to purchase another seat. Keep this in mind as team members inevitably come and go! You can read more about adding/removing users here.
- Firstly (re: privacy with names), each user will be able to choose what name they include in their Calendly account under their profile settings. I suggest telling all of your contractors to use their First Name + Last Initial or some sort of nickname appropriate for work, as this name will be displayed on their booking pages/invites sent to invitees and calendar events etc. Secondly, you can name event types (if created individually for each host) “Event Name + Host’s First Name and Last Initial” or just the first name. This is a very common method used by other owner/admins like yourself.
- Nope. There is not an internal comms tool (no messaging/emailing etc.) natively within Calendly, as it’s not a virtual workspace or CRM - it’s a scheduling platform! Users within your organization will be able to see the other members of their team (so whatever name is chosen/avatars/event types they are assigned to), but will not be able to view their personal profile information (where they live, phone number, email address etc.) and so on. If you’d like, you could create a free Calendly account and add yourself to a paid seat on your team before adding someone else - then explore as a user to see what the experience entails. Then, remove yourself and fill that seat again with a real team member!
- We have a Group Event Type that allows for one host > many invitees! You can set this up on a Team Page, as an Admin Managed Event or as an individual event for yourself at any time (and other users can set up one-on-one and group events on their own in their accounts separately from whatever you assign to them in a team environment/admin managed environment - there is no way to limit them from doing this - just an FYI!). Group events sound like exactly what you are looking for in this situation. You can include them in the routing process, too. To make this work, you can set it up so that if a potential invitee says they’re in X geo location and they’d prefer to meet in person (you will be given the option to set up “and/or” logic), they are routed to the group event type for that geo location. Or, you can come up with other logic that makes more sense for your use case and in your own brain!
- Oops… you didn’t have five on your list - but I don’t want to delete this because I prefer odd numbers. Sooo, here’s some articles and such from our community and our Help Center (starting with Help Center) that you might find helpful in addition to all of this info!
- Routing Forms Best Practices
- Let Invitees Choose Who to Meet With Using Routing Forms
- Calendly Routing
- Team FAQs
- User Management
- How to Distribute Events Round Robin to Team Members
- Multi-person Scheduling Options for Teams
- Understanding Multi-user Features: Groups, Teams and Shared Event Types
- Setting up and Managing Shared Events
Now, onto some super awesome community articles (I have a liiitle bias towards these for obvious reasons, but our Help Center content is honestly next-to-none as far as help centers go, as far as I am personally concerned… so this is all super great to reference lol!)
… PHEW! I know that is A LOT of content, and you certainly do not need to read it all right now. It’s all available here and in our help center annnyyy time you want or need it, but now you have what I feel is immediately relevant to your use case and questions listed here in your topic for easy reference any time, too!
HAPPYYY READING! 
Let me know if you need anything along the way. I’ll be back tomorrow!
Oopsie! Adding one more (short!) note here because I briefly mentioned it and added a link or two, but didn’t explain it to you myself.
You might also consider using groups to organize your team members (this is a different functionality than adding users to teams in order to assign them to team event types) internally. What’s bad about having more organization?
What the heck are groups? Well…
As an account owner, admin, or group admin (you can make any single user in your organization an admin of the organization itself, or an admin of a specific group/groups - or both!), you can place members of your organization into groups.
You can use groups to:
-
segment users based on department, job function, or location
-
delegate control to 'group admins' to manage and report on their group
-
view scheduled events and activity by group
You can also automatically provision users into groups if you are using an SSO! See more here.
To create a group, view Create a group.
Along with the info above, this should be helpful as you figure out how to set up, organize and sort your organization and it’s team members. Talk to ya later!
Hi Kelsi! OK, after reading lots of docs , still a bit unclear on groups vs teams.
Is this an either/or decision? Or can we use both, one for internal organization, one for external scheduling?
And if it’s an either/or, can you help me understand tradeoffs a bit more?
Many thanks!
Hi Kelsi! OK, after reading lots of docs , still a bit unclear on groups vs teams.
Is this an either/or decision? Or can we use both, one for internal organization, one for external scheduling?
And if it’s an either/or, can you help me understand tradeoffs a bit more?
Many thanks!
Sorry for the confusion - that’s a common pain point that I’ve noticed (mentally noting that we should put out documentation outlining these features in a compare/contrast format...) - let me elaborate and answer your questions!
Firstly - this is not an either/or situation. You can absolutely utilize both teams and groups within your Calendly organization, and with your complex use case I suggest that you do!
Now, to outline each feature (I am pulling this directly from our Help Center article, “Understanding multi-user features: groups, teams and shared event types.”)
Teams = where the scheduling happens.
When you create a team in Calendly, you create a team space for admins to control the team scheduling experience. Within this team space, admins can:
- Create and manage multi-user events (round robin and collective)
- Display events on a team landing page
- Upload a team logo
In the below example, we can see the Calendly Customer Feedback Team’s logo and landing page, where people can choose the team event that suits them best:
Expand the below section for more on teams, when to use them and how:
When to use a team
Most commonly, teams are used for either departmental or cross-departmental scheduling.
For example, let’s say you want to coordinate an event for a cross-departmental team, consisting of members from all over your organization:
Ryan, customer success
Kirsten, product
Melany, sales
You can create a team in Calendly, like a Customer Feedback Team, and set up collective event types for feedback calls. Calendly will only offer availability when all teammates on the feedback call have availability:
Image 4. A team space in Calendly
Even if teammates are in different groups or departments, they can come together under one team. Accordingly, we can imagine teams as the bridge between groups:
Image 5. A team can bridge multiple groups
Admins and team managers can manage teams
As an admin, you’ll have complete control over the team, so only you can edit and create team event types. You can also designate a team manager, if you want to share editing access.
However, sometimes users want to be able to quickly set up a collective or round robin event themselves, without needing to go through an admin.
That’s where shared event types come in, which we’ll explore in the next section!
Key team takeaways
Teams allow you to…
Set up multi-user events with teammates
Create a booking page with all your team event types
Have complete control over the team scheduling experience
To read more about teams, check out Set up a team page.
Teams are available on the following plans: standard, Teams, and Enterprise.
Onto Groups!
Groups = people administration made easy.
With groups, you can organize, manage, and report on everyone using Calendly in your organization.
Expand the below section for more on Groups, when to use them and how:
Groups work well for departments
You can group people together however you’d like, such as by location, job function, or scheduling need. Most commonly, groups are used for people in the same department.
Let’s imagine you have three different departments within one Calendly account: customer success, sales, and marketing. By creating three separate groups within Calendly, you can separate important admin functions, like:
- Reporting
- Onboarding
- User permissions
Image 2. Examples of groups by department
Groups let you delegate admin tasks
You can delegate a group admin to manage admin functions. A group admin will have access to reporting around account activation, usage, and scheduling, such as:
- Who has activated their account
- Who has connected their calendar
- What video conferencing platform users have connected
- Total scheduled events per user, including last 30 days
- Date of last booking
- Days since last scheduled event
Groups help you consolidate accounts
Lastly, you can use groups to consolidate multiple Calendly accounts into one account. That way, your multiple departments can live under one account and one bill.
Key group takeaways
Groups allow you to…
Organize individual users by department or other common characteristic
Improve department performance with activity and usage reports
Delegate a group admin to manage users
To read more about groups, check out An overview of groups.
Groups are available on the teams and enterprise plans.
You can head to the article linked above to read more.
We also have plenty of resources for you to learn about creating a team and setting up team events! The first step is adding your desired team members to your account from your Admin Management page. Then, you can set up a team page. Your team page will have all of your events specific to that team: round robin or collective.
Round Robin events will allow your invitees to book an appointment at any time at least one assigned team member is available. Collective events allow invitees to book an appointment when all assigned team members are available. If you'd like a more thorough breakdown of the team features, check out this recording that walks through the basics of using Calendly with your team.
All of that would be done with Teams - to set up actual scheduling. Then, you can bring Groups into the mix to organize more internally.
Paired with the resources I provided to you in my earlier comments (and now with the ability to make more sense of Teams vs Groups and how they can both benefit you), I think you’ll probably have all that you need - but please let me know if you don’t! I’ll be here.
