I work (first "sidejob", 2 years) for a company who's offering me freelance work. It's great. It pays extremely well.
There's a person in a management position who organizes our orders. Previously the communication and cooperation went smoothly, friendly and just great, with the manager and the team. It made me put in the extra effort or work when they needed, help them with questions, etc. It wasn't part of my task, but I enjoyed it and felt valued.
However the company itself has, to my idea, a high turnover rate (I suspect from underpaying their employees/lack of growth opportunities, risk averse business model, not my problem), and they had some struggle in filling the management positions.
I cooperate much worse with the new person in the management position compared to the previous 2. Previously I felt appreciated and not "used". However this new person tends to not show appreciation, make me feel used, and gives feedback that is unnecessary harsh to the degree the team turns to me for guidance more often. There is a general vibe that she feels she needs to milk every margin, at the expense of others (what I do, and the company itself is already very profitable). She got promoted from within the company and has close ties with the one who runs the company. I feel like she wants to "prove" herself, but what she does is very counterproductive.
I am not in the position to give her direct feedback, and hints given to her would been taken as a harsh personal attack.
I am playing with the idea of sending the head of the company just a message with the scope of "Hey I've worked with your company for 2 years, and with great pleasure. I felt appreciated and went along well with previous managers, however the current one is a bit of a hassle, and is therefor reducing my work pleasure. I don't know how to give her the feedback directly, just so you know, good luck with it".
I've made enough money to be able to lose the job, but it would be a pity. I don't want to ruin work relations, being well aware it's actually none of my business. I am an outsider, and it's kinda weird the way I want to inform them about the dysfunction of one of their employees. But then besides the job, it seems I've nothing to lose. How would a company react to such a message? And would there be a possible reward in being this directly as an outsider, unrelated to the manager in question?