Step 1) On the ACCOUNT LEVEL: Go to Settings> Phone Dialer & SMS> Edit> Caller ID
On the USER LEVEL: Go to Account> My Information> Caller ID
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Step 2) Enter in the phone number, give it a nickname (ie. "Office", "Cell") and add any associated area codes.

Step 3) Click VERIFY CALL.

Step 4) Answer the phone call. Enter the verification code next to the phone number. (You have to press the keypad icon
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to type the #s in). If you've completed the verification call and the # still looks like it's not verified, click the blue hyperlink "Verify" and it will force the udpate.
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Step 5) OPTIONAL: Set as the Active Caller ID or for Area Code Recognition
 If you want to have different Caller IDs automatically display for different area codes, you can assign phone numbers to display as the caller ID when you call that specific area code. The Active Caller ID will be the default for any area codes not specifically set via the area code recognition. Click SET AS CALLER ID to make that number the Active (or Default) Caller ID.
 For example:

In this example, we've added a California local Caller ID for the California area codes, a New York caller ID for NY area codes and are adding an Illinois caller ID for IL area codes. For all other area codes, the Active Caller ID will be the default phone number.

OPTIONAL:
If you want to assign your team members specific caller IDs, go to Account> Manage Users> Edit the User. Go to their Caller ID tab. The number will still need to be verified, so make sure that the person can do so if you don't have access to their phone. Otherwise, you can have them do this step themselves.