newbie having hard time finding 1st cdl b job

To the OP: You picked a bad route to go. Plain and simple. And your "boss man" should know already what his insurance provider requires. Maybe it's for the best you don't work for him.
Unlike Class A jobs, you're not going to find a big "dump truck training megacarrier". They're not going to spend a month or better training you how to drive a truck. You'd tag along behind another dump truck driver for a day or so, they'd teach you how to operate the PTO, show you which material goes into which stock pile at the asphalt plant, etc.
The guy who wanted to hire you might know you well. Insurance providers don't know you from the next guy. They don't have the benefit of knowing, "well, the guy looking to hire him on knows him well, trained him personally, etc". All they see is a rookie driver with no experience.
Should've gone the Class A route, IMO.

 

I started pretty much the same way with a class B license back in the 80s. Took what i could get and stuck with it. It was LOW pay and crappy companies but thats how its done. Drove for over 23 years moving slowly up to better pay with each job at various companies. My last driving job was earning $52k, home every night, no weekends and 5 weeks vacation a year. Look for locally owned companies that have tractor trailers and bobtails. Put in apps and follow up relentlessly! With no driving experience it will take persistance and a gung ho attitude to get in. Stick with it and no matter how low the pay you give 120% everyday.

Good Luck!

 

Insurance companies run this world there no way around them...

Most likely without any experience you an't going to find a job and being in Florida,forget it.Best bet is get your A licence,get a year or 2 experience and then look for a B job if you don't want to drive 18 wheelers