Design is subjective... if you don't have a defined brand. I've sat through meetings hashing over which icons, photos, and colors to use. It sucks. Most likely, these kinds of conversations fall onto the executive order of whoever is in charge, like a CEO or equivalent position. Apart from the issues of scalability and freeing someone like a CEO to do what they are best at, it's a shitty situation to be in. Spending all that time trying to figure this stuff out only to have the decision be made by someone else. Not because it's the right decision, but because it was their decision.
Get aligned. Spend time diving into strategy. You will save hours in the long run. More importantly, you will have an objective viewpoint for creating things in the future and give your team freedom to move.
If you don't know where you're going, nothing will help you get there. No map, no compass, hell, not even the stars can guide you if you have no aim.
What do you mean a rebellious logo?
Well, rebellion in its simplest form is this: when everyone goes left, are you willing to go right? Rebellion means looking at the context your company is in and figuring out what is missing.
At the onset of every identity project there needs to be a common goal between the designer and the owner of the logo. This goal is assessed by drilling down on the story, voice and tone, character, ideal customer, and the mission, vision, and purpose of the brand.
After getting introspective about who you are, you need to see what's already out there, especially in terms of a logo. It's astounding to see how the marks used by your competitors are similar. In fact, I'd guarantee you find at least two recurring motifs like an image or color palette used multiple times. The goal here is ascertaining what NOT to do.
After observing what's already out there, now you can formulate concepts that are different from your competitors. My recommendation is to think of them in categories: a pictorial mark (something that is a representation of a real object), typographic (word-based mark), and abstract icons (shape-based marks that don't resemble something real). You'll find that at least one of these categories makes up the majority of your competitors' logos. Don't pick that one.
Black and White:
Every good mark works in both a solid black and a solid white version. If you have to rely on color to make the mark effective, go back to the drawing board.
If you're good to go on the black and white versions of your logo, move into choosing colors. Remember, the key is to choose elements that are different from what's already out there.
Logos are special because of the things they live on. By placing your mark on business cards, marketing collateral, signage, digital environments, and at varying scales, you can forecast against placement issues in the future. This saves thousands of dollars ensuring that the mark doesn't incur printing hazards down the line and can retain its structure regardless of where it goes.
Go get em rebels.
How much marketshare do you want? All of it?
Wow. That's an ambitious goal.
You want it now? Dang. Sounds like you're a real go-getter.
You can't have it.
At least not now. You're not ready. But there is a clear starting point that every successful software out there has shown us: build for neophiles. The innovators and early-adopters. It simply doesn't make sense to build for anyone else. Here's why:
Whenever we create something truly novel, we engage in pattern interrupt (thanks Seth Godin). Pattern interrupt places a user in a state of decision making, since they have encountered something outside their normal pattern of behavior. Slack, before it was adopted by every single organization worth talking about, was a pattern interrupt. Most teams communicated via email, text, etc. Not very effective. Even so, the thought of switching from the normal, (albeit shitty) pattern requires energy that people don't want to spend... unless trying out new things is their normal.
The only folks who fit that pattern are neophiles. They are people who want to find something new, who want to be in-the-know, and who are joyous when they find something novel they can test. Furthermore, they are the first stepping stone in gaining mass marketshare. If you want the masses to engage with your product, you have to first rally the Neophiles.