Not so much a crappy boss, but a crappy company.
Right after college I worked for an auto insurance company as an adjuster. BIG mistake. I did meet some awesome friends there which I still hang out with to this day, so that was one plus.
To start, I didn't get paid for a month. They kept saying there was an issue with the direct deposit not working, which interestingly enough one of my friends I met there had the same issue. After we both went to HR suddenly our checks were in the mail and the direct deposit problem worked itself out...
The issue with this company is their claims management. I found out later that there was a 50% turnover rate every year for new employees, so not only were we understaffed, but a major portion of the staff were brand new, and had very little knowledge of policies, how to update claim files so information was accurate for customers, etc. For 2 hours a day, we were on what was called "queue calls". This means we would take incoming calls for the company and work other people's claim files. The problem with this meant that the new staff were working in your claim files, screwing up your claims, which the company held you responsible for.
Your manager also had a console with everyone's time. You had to swipe into the building, which notified your manager you were in the building. You didn't officially clock into work until you logged into your phone program on your computer. If you had a computer that was slow... that meant you better get to work a bit earlier. We had to use that phone program to sign out anytime we went to lunch, the bathroom, a meeting, etc. If we were gone for 1 minute longer than the allowed time (30 min for lunch) a notification warning would pop up on your manager's screen. Everything was tracked, the time you were on phone calls with customers, how many phone calls you returned, when you returned them in relation to when you received them, how much money you paid out to insureds for damages, etc. I was actually investigated 3 times because of the amount I had paid out to insureds for damages. Each time I was 100% correct, it just happened that I had a lot of totaled vehicles that week resulting in a higher payout. This basically meant that you had to be walking in the door for work at 8:10 if you clocked in at 8:30. If you wanted a coffee, you better get there at 7:45 so you have enough time to go to the cafe. We were all salary, and were scheduled to work until 5pm. If we had a call before that, we had to take it (remember everything is logged on your manager's PC). There were many times I got a call at 4:55 from a customer and didn't finish until 5:30, 5:45, or 6pm.
Oh and we had 2 weeks vacation, but good luck trying to use it. Since a certain number of staff needed to be on the floor at all times, there was a lottery for vacation time, and the most senior employees (100 or so employees in my dept) got to choose first, so anything from June-September was all blocked off. That includes doctor's appointments, since sick/vacation time was all considered PTO.
The company required us to do 10 hours of training a week while getting all of our claims done. I was also threatened daily by customers who were denied the coverage they expected (people wanting $20k for a 12 year old Civic that was a total loss). My customer service performance was dependent on a survey that played after every phone call, which was BS.
I argued with management on this one since it was completely useless. Most people having been in an accident would still be pissed even if you gave them a new car, and most people hung up before the survey anyway, leaving only those who want to give negative feedback.
Also, if you were male, your chances of getting higher in the company were slim. All the managers were gorgeous young 20 something females who clearly slept with all the 50 something male directors. Many of them were clueless about anything policy related, one had been there a month before being promoted. And I don't mean that as an assumption, they actually had to make a rule in the company a month after I started that you could not have a sexual relationship with a superior. They apparently couldn't figure out why their turnover was so high.
My friends left soon after I did, and we all agreed that you couldn't pay us a six figure salary to work there.