It is hard to give effective general advice in terms of applying with companies as we never really know the perspective of the recruiters or hiring managers unless we have experience with them personally. Some don't mind it at all, especially if they see the roles are very similarly aligned and they understand where people are coming from in the market right now.. others see it as a red flag. The best way to navigate this is to understand why they would see this as a red flag and address that concern.
Organizations who don't like seeing candidates apply to multiple roles generally feel this way for 2 reasons. 1- They want to find the right fit for each role and if you are selling yourself as the right fit for several roles, then they can't trust what is true for any. 2- They may be interested in employees with some bit of longevity or at least a high level of engagement and if you'll take just anything they don't see that in you (that'd be like dating someone who is with you because you're the first person who asked them out.. not ideal).
For the first, if the roles are closely aligned, maybe try being upfront about the multiple applications and explain what the common thread is that attracted you to each. Instead of naming a preference, use the process as a discovery process and ask the recruiter or whoever you are in contact with if they have information to help you determine which one is the best fit for you. Now you're working together on finding you a place in the company!
To address the second (and it works for the first), in conversations be sure to focus on how you are connected or aligned with their mission and/or culture.
Another tactic altogether is to reach out before applying to anything if you see a company you are aligned with that you know could benefit from the type of work you do. Try to find a connection there in leadership or HR, tell them you really want to be involved in the work they do, talk about your strengths and how your skills could benefit them and ask if they see potential for a role fit. This tends to work better with medium to small organizations (the big ones that everyone wants to work for of course have too much noise and competition) but I have done this before and landed a job that hadn't even been posted yet.
And finally, remember, you don't know the hundreds of things that go on in their office while you are in the application process. Often, the decision not to go with you has very little to do with you personally or what you have done. And if it was something you did, it doesn't always mean you made a mistake. It just means THEY didn't like it.
Good luck!
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