Once you get some contracts under your belt, and get your reputation up, you will be able to afford better gear, especially once you are able to secure Noble contracts. You will also be able to acquire some gear from your fallen enemies. Choose your "perks" wisely. I think once a man hits level 11, you get to choose 2 perks and then that's all you get. Your front line "tanks" definitely need Steel Brow, Brawny, and Battle Forged. I also chose Shield Expert for my tanks, but now that I've switched them all to 2 handed weapons, that's a wasted Perk for me.
My favorite contract now is a Noble one, patrol and collect heads. My guys are strong enough that I will often just head straight to a stronghold and attack it. Fast way to get heads without relying on random encounters.