DM Academy

That’s such a fun idea! What if they had to do some extractions that have different requirements to complete. I think it would be fund to something like a stealth/heist mission to get a special tool and an extraction mission to save the specialist that uses the tool. It would be cool to bring back some of the minor characters from previous sessions as obstacles too as a throwback.

I'd suggest putting together a few resumes. Use some online generators to add backgrounds and plot hooks.

There was some DriveThroughRPG supplement for Waterdeep: Dragon Heist that did something similar for tavern staff. I put together:

• Rumboldt the Racist Dwarf, ex mercenary who interviewed to become cook (orcs killed his son, he will attempt to poison any orcs/half orcs that enter the establishment)

• Xltr, a black cloaked something. It's face can't be seen. Mixes really good drinks. Doesn't speak. (actually three kobolds in a magic cloak)

• Dannis, an extremely handsome and charismatic human from another city. (He will be kidnapped by the spouse of someone he picks up in the bar)

• Illiria, a young elf, clearly slumming with humans to anger her high-born family. Shows absolutely no interest in getting the job, or capability to do it. (If hired, she will be slighted by an employee of a competing organization and devote herself to destroying it, probably by doing her job well and attempting to sabotage the other org)

So depending on how "gamey" you want to make it, I could see implementing an aid type of system. The idea would be for each task or quest or whatever thing it is each group of NPCs is doing, there would be a behind the scenes roll with a DC based on the difficulty. Your party, through interacting with NPCs, setting up appropriately during downtime sessions, choosing the right combinations of mercenaries for a given job, etc. could modify or otherwise have an effect on that DC.

Say for example one task the mercenary company has available is to escort a carriage to the next town over to deliver precious cargo. The PCs could handle that, but maybe they'd rather let some of their fellow mercenaries handle it instead. You might know a group of bandits is waiting along the road, so it would be say a DC 15 to see whether the cart makes it safely. The party might choose to send a veteran mercenary (-1), might make sure the carriage is well armed for the journey (-1), and might have a conversation with a younger mercenary also slated to join the trip to try to boost her confidence (-1). So the final DC based on the party's preparations would be 12. It could also make sense to use a success/failure threshold like how Pathfinder 2E handles things. If you fail the check by only 5 or less, maybe the cart still makes it but some of the goods were destroyed in a scrum. Fail the DC by more and the cart might get completely lost. Or maybe the young mercenary is kidnapped and has to be rescued!

This is just one example but it really depends on what sort of framework you have in mind for the types of tasks their fellow mercenaries will be performing. Best of luck to you!