as @Liam Green said - this is not possible out of the box in Jira. This is why we have developed Customer Tools app that helps to achieve such goals. You can define separate fields layout for customer and organization. The checkbox field is one of many field types available. For more details please check documentation.
Could you clarify your need about fields for users (people)? Are you asking about standard Jira users, who are not Jira Service Management (old Jira Service Desk) customers? Where you think such fields should be visible?
To add custom fields you need to be a Site Admin. If you have this permission then you just need to do the following:
Click Settings Cog > Issues > Custom Fields > Add Custom Fields
The below document should be able to get you through it:
Hope that helps,
Sorry, I thought you wanted extra fields for customers and users to fill in on issues.
As that doesn't appear to be what you wanted, could you clarify the following:
Are you looking to add a field to the user profile containing their phone number? And Another field to a user profile containing a checkbox?
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