Hi there! I hope I can clear this up for you.
Not only is it possible; it is the only way that you can pay for premium, as paid plans apply to workspaces, not users, not accounts, and not boards. There is no such thing as a "premium" user. There is no such thing as a "premium" board. There is no such thing as an "upgraded" account. Only Premium Workspaces. Premium Workspaces may have unlimited boards and unlimited users.
All boards in the Premium Workspace will have premium features available to them, and all users in the workspace will have access to the premium features in that workspace only.
The cost of a premium workspace is calculated per billable user, however. So if you have 3 billable users in a premium workspace, then the person paying for the workspace will pay:
3 x the cost for Trello Premium.
NOTE: If a user in the Premium Workspace is only added to one board, then they are considered nonbillable and you don't have to pay for them, but you have to have Trello Premium to do that. Otherwise, on free workspaces, the limit is 10 users for the entire workspace, not just that one board.
https://support.atlassian.com/trello/docs/how-billing-works-with-trello-premium-and-standard/
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