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I always ask.

As a customer, I don't give any weight to these badges because I've known startups that have lied about them.

As a product owner, I see multiple benefits to ask for it:
* talk to your users: you will always get something out of it
* turn a badge into a testimony
* turn customers into advocates: some customers will be willing to be contacted by your prospects (this may not apply to what you are selling)
* get better resources: sometimes the logo is not easily available in the best possible format for your use case
* avoid trouble: some companies are very careful about how their name is used, and your users might not like it if they discover the logo of their company when they know to be the first users there
* be nice: it's a basic courtesy, you will use their name for your benefit, be transparent

My experience is that most of the time, people will be happy and even flattered if they truly like your product. And you could end up with a sweeter deal than just a logo.

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