We need to talk about this new... pivot. I know you're getting a lot of "positive" reviews in the press. But let's be honest: most of these reporters aren't digging beneath the surface about what's really happening.
When you talk to task posters (like me, who has posted 50+ tasks) you find incredible frustration. I had a particularly busy weekend and was counting on some of your amazing taskers for help.
This was easy before. I would just post a task (~2 minutes) and wait for some offers. Each offer typically came with a 1 - 2 line sentence description of why they're a good fit. I would then see who's the best fit based on those descriptions (reviews were less valuable since almost all are positive).
It was a quick, easy, and all-around wonderful experience. That's important since, after all, I'm using TaskRabbit to save me time and effort.
Now it's totally different. You've put all the manual effort of finding someone on me. And it doesn't even work. (Did you forget that I'm using TaskRabbit to save myself time?)
With this pivot, I have to crawl 15 profiles (that's all I get!) to find someone who's a good fit and available. 75% of those people aren't even available and the remainder might not have the right skills. If I can find someone who's a good fit and has listed availability, they still usually aren't available. So I search, book, get rejected, search, book, get rejected, and so on. If I'm lucky, after hours of effort, I might successfully book 1 of the 15. But often that doesn't even work.
The end result is that posting tasks is a tremendous waste of time and energy. I love(d) TaskRabbit. Huge fan. But now, I find myself not using it. It is a chore to use it.
I don't think that's what you want task posters to feel. It sort of defeats the purpose of your product.
For taskers, the situation is even worse. They're struggling to find jobs. They were depending on TaskRabbit to pay their bills and now they can't.
Not cool. When people are depending on you to meet their basic needs, you need to be really, really careful. Communicate what's going to happen and how it will impact them.
But you didn't. You didn't tell people who needed their TaskRabbit income to pay their bills that they might not be able to do that.
You probably - hopefully - didn't know. I presume that, had you known that it would mean task posters unable to get help and taskers unable to get work, you wouldn't have proceeded with this pivot. It defeats the point of your product, after all.
Let's face it. What you rolled out was sort half-baked. No filter for availability. Lots of bugs. You abruptly cancelled all in-process tasks. I can't ask someone questions before booking them. Your auto-reassign feature exposes my address to people without my permission, which is a major privacy violation. 15 profiles is just not enough to pick from (not after you account for availability and skills). Time slots are too rigid (8am - 12pm, 12pm - 4pm, 4pm - 8pm).
It's a flop. Sorry.
I understand this is hard.
No doubt you did customer research that pointed you in this direction. Maybe that direction was right, but the execution was flawed. Maybe with a few more features it would be great. I don't know. I don't care. Right now, it doesn't matter.
The product you have right now - the product your users are depending on - isn't working. You don't have time to spend the next couple months figuring out how to make it right. Your taskers will move on to other jobs because they have to. Your task posters will stop using it because it's not worth the hassle.
Maybe there is some really compelling product that can be created and this approach is on the right track. But you can't figure that out while your users are abandoning you.
Flip the switch. Revert the pivot. Go back to the drawing board. Then figure out what the right future is for TaskRabbit.