I did the design for my app myself because I'm cheap. I currently have a "logo" that is just some font I found, nothing serious. Now that I've released Trig I wanted to get something that looked a little more professional.
I was hoping to spend under $500 because again, I'm cheap. So my first stop was 99 designs. 30 designs, nothing was even close to what I was looking for. Ending up getting a refund there.
Then I went to Dribbble and started emailing people that had some good designs. I got quotes from $600-$20,000. Since I'm cheap (this is a theme here right?) I went with the $600 one. It was $300 up front then $300 for the rights to use it.
First round of designs were... ok? Like they weren't absolutely horrible, but nothing really that exciting. It was a small step up from 99 designs. We went through 3 rounds. I gave him more details each time hoping we would get closer to no avail. After the third round it was clear I wasn't going to get what I was looking for, so in favor of not wasting any more of his time I cut it off.
I think the issue with the first designer is based on his Dribbble he just didn't have a lot of experience with wordmarks, or more abstract concepts that you might face in a SaaS. All of his designs we for restaurants and what not with a very clear image he could use, for example a duck or a mug.
I fixed that problem the second time around and found a Dribbble designer that had a lot of logos for more abstract concepts like Trig. He also had a lot of wordmarks. So I took the plunge and spent more than I was hoping.
He came back with the first round just a couple days after I paid. The first one was great and I said let's go with that. There was only one small change.
I'm pretty happy with it, check it out and let me know what you think.
TLDR; - Make sure you find a logo designer that has some very clear logos you like, but also for companies similar to yours. My first designer for sure was talented, just didn't have experience with logo's like I was looking for.