Our agency is also a small family-owned agency. We have 15 employees and we do mainly commercial insurance. I have transitioned over the last 3 years to almost 70% benefits.
I am a big believer in making lots of in-person cold calls and email marketing. I make a lot of phone calls why I drive around all day too. In my opinion, you must set up a pipeline manager/CRM and track everything! You can also create email templates which makes cold/warm emails much easier to duplicate.
As far as how am I selling groups...I lead with ACA and ERISA
compliance, ben admin assistance, and helping employees understand their benefits better...its been my experience if you lead with a price and a spreadsheet you will lose almost every time...especially since 50 and under pricing is the same for all agents.
I also show the clients how much their current agent makes on their group, and then ask them how much service are they really getting for all that commission. Other agents seem to really dislike that, but it has worked very well for me.
I really like Zoho CRM, but you have to spend a lot of time setting it up. Pipedrive is another really good and easy way to track calls. I have seen some interesting sounding CRM's on the Tech Forum too.