The thing that drives me absolutely bonkers with Asana (others do this as well) is that the freelancer has to upgrade their "free" account to roughly $70/month to get functionality like seeing a Timeline (think Gantt). Their pricing isn't clear that to upgrade to Premium (to get Timeline) says it's $10.99/month. It's not until you get to the next screen that it tells you it's 5x10.99/month because there is a five person minimum.
Almost none of these project management tools are built with full functionality for a freelancer who manages projects and people doing the tasks/projects, but doesn't need them to log into the project management tool.
Single-license freelancers are never the target audience. From my experience running a similar business, this is the hardest category of customers to deal with. Stuff like demanding very project-specific features for free overnight and cursing you when you explain how requests are prioritized from user numbers. Or demanding instructions on tangential topics (like how to troubleshoot some network issue their customer has) by claiming that it stops them from using the product.
I mean, there are nice guys as well, but statistically it's just not worth it.
Most single-seat customers are fine, of course, but a very vocal minority can cause a lot of problems.
I believe it's due to the mindset shift. If a team or company decides to use a specific software, people are more likely to accept the decision and learn to work within the tool's features and limitations. The cost of switching tools is high, so they tend to stick around for a long time.
Single-user freelancers can change tools at any time, because they don't have to negotiate with anyone else. As such, they feel they have more leverage in threatening to cancel their subscription if the company doesn't cave to their demands.
Most of them don't realize that the company isn't making much, or any, money off of their single-seat license when they're consuming hours of customer support or social media engagement time every month. It's better to see the squeaky wheels just leave the platform.
For another data point: At scale, you get a lot of threats from people claiming they're going to Tweet about how bad your product is to their thousands of followers, or write a newsletter about how much they hate your product, unless you implement the specific feature they're demanding. These threats exclusively come from the single-seat users, because no company is dumb enough to try to extort another company with threats of tarnishing their reputation in public.
It's unfortunate, but it's true. It's vastly easier to just deal with enterprise customers or larger teams who have better things to do than tie up customer support time for every little complaint or suggestion (or demand)
Fun fact. If you don't reply at all, and completely ghost them afterwards, no matter what they say, the chances of them carrying anything out gets close to zero.
I'm not sure I'm really buying your statistics. There are ways to go about prioritizing roadmap items that aren't rooted in customer size (think UserVoice). The company can also have a well documented and published roadmap so that I can easily see what's coming down the pipe and whether or not it's going to factor into my buying decision (I get item x which is something I really want - in a couple of months).
Dunno. You can look at their pricing tiers for yourself: https://asana.com/pricing. Also, it's not obvious that the Premium tier and above, despite saying it's "per person/per month", it's 5 person minimum. Gah
I am assuming that's on purpose. For them the number of people on project is proportional to the money they can earn. Why would they cannibalize their revenue by allowing shadow profiles.
Edit: re-read your comment. It seems like you clarified or I missed about the five person being the minimum thing for that.
I simply put tasks in Asana and want to view it on a timeline like a Gantt chart. I can't do that unless I pay 5x10.99/month. There is a huge gap between $0 and $70/month.
What revenue are they cannibalizing if I'm not going to go from $0/month to $70/month when I'm only one person? They just lose me as a customer going forward.
Almost none of these project management tools are built with full functionality for a freelancer who manages projects and people doing the tasks/projects, but doesn't need them to log into the project management tool.