I'd argue that the problem is not that you raised the prices but the user increments are set way too low ... to appeal to teams I'd have the cheapest plan be at

I'd argue that the problem is not that you raised the prices but the user increments are set way too low ... to appeal to teams I'd have the cheapest plan be at least $99/year maybe the full $149 but also give them 5 users by default - then allow a monthly option which effectively forces people to pay a 10-15% ish premium over the yearly option. Then make a plan for say up to 15 or 25 users that is substantially more expensive and finally the unlimited user plan could be even higher. Because you're able to do so much inside of one application I could easily see companies paying $1k+ for parts of this on a yearly basis especially when they had 20+ users of something like the task management tool. Personally I'd also suggest modularizing your different pieces (so you can just buy the project management or just buy the invoicing etc.) As teams get larger they may want to do more or do less inside of one application, you dont want to have people feel like they're paying for things they don't need if they arent using them. Just my $.02 I know all this takes a lot of work, but the product looks great, I hope you can figure it all out! Best of Luck!