Hey, I’m pretty sure you’ve already thought about many ideas, but here are a few that pop into my mind:
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Enterprise support plan : a premium offer that includes quick dedicated support, or maybe a dedicated coach/technical support
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Custom development : maybe you could offer this as a service for companies that would like to modify/add a functionality to their Penpot instance (although if it helps someone, if might also help others, so it would make sense to have it as a plugin)
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Training: group or 1-1 classes
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White labelling : give the ability to modify the Penpot logo and other things …
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Advanced security features : you could offer to host some instances on an encrypted server, with advance security features such as 2FA
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Create a premium bundle package with Taiga (especially if it’s planned to integrate Penpot comments into Taiga)
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Sponsorships/Mecenat : for events, or regular donators that support the project in exchange of visibility
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There might also be the possibility to generate some revenue through selling premium templates or giving access to premium plugins. But it has to be well thought (I’m thinking about the WordPress plugins library model).
