AT&T Cost??

Here at work we have an old family plan of 2100 minutes per month, 5 dumb phones. After taxes and all it's about $195 per month.
The boss wants to bump up to a smart phone as well as I and another, so that would be 3 smart phones and 2 flip phones on the plan. Either way I look at it's gonna raise the price up to around $250+.
How are these new plans saving money??
I have a Galaxy S4 I can use but we would still need 2 other smart phones.
I'm not paying the bill but I know the boss doesn't want to pay $60+ more per month either.

What's the best route we can go? contract, next??
Thanks,

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With a new contract you could potentially get 5 new phones for free. If you don't need 4 of them then you could sell them to make back some of the money. Make sure to get the most expensive phones you can for free if you're going to sell them. With any smart phone you're going to have to pay for some kind of data plan, so that is always going to cost more then just voice.

The alternative is doing everything pre-paid, but you'll have to buy another phone outright.