Ask IH: What kind of growth strategies works and does not in a crowded market ?

I can't answer to the first 2 questions but can attempt a semi-coherent response to the last 2:

1. There is no single answer to increasing conversions. It is a combination of a bunch of things like: design, sign up flow, trust, pricing, positioning, traffic source, copy, technical functionality, appeal to specific challenges not answered by other tools etc.. This is just the tip of the ice berg. It doesn't help that you are in a super competitive space with a TON of other solutions. Even if you get people to sign up you have to worry about high churn. If the software lacks one critical function someone is looking for in their project management tool, the user is likely to go seek an alternative. To cut to the chase, you'll probably want to re-design the front end, and the flow for starters. You can go to any major competitor and see what they are doing - inspect their design, their flow, and what happens after you sign up. Look out for email sequences, onboarding guidance, tool demonstration etc. Honestly, all of these things have been drilled a million times on a million blogs out there so there is no shortage of "best practices" to follow. That being said, I want to throw in another resource (my side project) that is new, but may be of help to you either now, or later. Check out my profile and follow that link.

2. I think your last question is the wrong question to ask. It assumes that just because a strategy is part of a saturated market it means it won't work. I think a lot of it depends on your execution. Take ads for example. You'd think you can't possibly sign people up via advertising in a huge market like project management, but there is always some edge case that is not being resolved by major players. If there weren't, there wouldn't be so many options. I think what's going to make the most impact for you is figuring out why your previous users chose you over all the other options out there; figure out who they are exactly and then look for ways to get in front of more of the same people.

You could always work on improving your product, but that takes time and money. I think it's much easier to clean up your existing product and empathize with your current users to be the best in class for whatever use case you are addressing for them. Then you can apply any number of growth strategies to your niche audience. I'll be adding more resources to my side project, let me know if there are any specific areas you want to tackle so I can find examples of companies who executed successfully in that area.