The fact that they are smaller, and/or privately held does not necessarily mean they will be lax on training. They may even be more thorough, you never know. Best way to find out is to talk to some of their drivers.
On the other hand, being smaller, they may not have a benefits package / insurance plan as good as larger companies. As a rule, the larger the insured pool (which is to say number of employees) the better the benefits and lower the price. This isn't a hard fast rule,as some small companies really go the extra mile to provide their employees with the best and some large companies are too busy counting pennies to really care about their employees. Since it sounds like an important issue to you, I would look closely at what they have to offer benefit / insurance wise. See if they will let you browse an insurance information package, etc.
If all the bennies look good, the money is right, their safety record is solid and you hear good things from their drivers, then I would jump on it. Do your homework before you jump in, no matter where you decide to jump.
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"I'm back out on that road again, I'll turn this beast into the wind, there are those that break and bend, I'm the other kind." -S. Earle
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