I think the individual working for the dungeon lord would be better in my opinion. Have the PCs start off as lackeys, henchmen, higher ranked minion, or whatever (assuming they start of at LVL.1). Have them work along side one another, in the beginning but have some incentive for PCs to "take initiative" above their fellow "comrades" later on. I agree in Daniel B.'s post, you don't want them all gunning for each other right off the bat. Find some reason for them not to, it's up to you. More than likely at least one of them will try to become top dog, creating a behind the curtains politic game of wavering alliances between players and back stabbing. While trying to remain in the graces and prove themselves to their respective superiors who will vouch for them, reward them, or take credit for their actions themselves and throw them under the bus if things go wrong. With the game being based on the bad guy's spectrum, you can do some really crazy and interesting things. Assassinations, illegal deals and trades, extortion, burglary and thieving, political corruption, backstabbing, black markets, kidnapping, starting wars, collecting and selling organs, torture, acts of terrorism, running supplies, arson, blackmail, bounty hunting, fight some of the forces of good, and so much more. I also like the working underneath a dungeon lord/master, because it also prevents the players from just doing whatever they want and saying "I am part of an evil organization and can do whatever I want." If they are part of an evil group, I really doubt their dungeon lord/master would want them doing evil things all over the place that are not in anyway shape or form is in the interests or benefits of their evil organization or dungeon lord/master. For example, randomly killing innocents and NPCs for no reason = this alerts local authorities of the PCs which in turn may threaten the rest of the evil organization or the dungeon lord/ master, which would be a big "no no". In fact, I would go so far as to have their first quest to be to kill a member of their own organization who is just going around killing people randomly and attracting too much attention, and must in turn be put down. And emphasize that if they become a liability to the organization, they can be easily expended or replaced. Which should hopefully squash any ideas of "I am bad guy = I can do whatever I want, with no concern of consequences." Another thing, is this all falls apart if the dungeon lord/master isn't someone who is feared, respected, honored, or whatever by his own men. If they are the dungeon lord/master there must be something that allows them to do so, and not be easily removed or replaced from their position. If there isn't, then what is stopping the PCs from just replacing him right off the bat? It's OK, to have the PCs eventually do so, but this has to be a really long term goal. But over all the key to all of this, is have a "good bad guy" as their boss/dungeon lord/master. A few others and I have actually posted a guide/tips/information in a previous thread about making a "good long lasting bad guy". Here: <a href="https://app.roll20.net/forum/post/399273/rookie-gm-needs-help-badly#post-409680" rel="nofollow">https://app.roll20.net/forum/post/399273/rookie-gm-needs-help-badly#post-409680</a> You can use this to help create a villain/boss/dungeon lord/master for your PCs to follow. Or help your PCs create their own evil characters.