Peasants moved up be to employees: those who work

The commoners or peasantry were the largest group in medieval society. They were the farmers, servants, craftsmen, laborers, and merchants who made up ~90% of the population. They did the work to produce food and goods, and paid taxes and rents to the nobility in exchange for their protection. The majority of the populace was rural, living on a farm or in a village near the lord’s manor. Of course, someone had to supervise the labor, collect the taxes and rents, and manage the day-to-day operations, which created a hierarchy below that of the noble ranks. And that lower hierarchy finds parallels in the corporate world today. 

Steward / seneschal / majordomo  

The steward was the Chief of Staff for the Lord. This person was the top commoner in charge of all the servants on the manor, both for the lord's estate and for his household. A very rich lord might have multiple estates, and the steward was in charge of them all.

This is middle management, maybe lower middle management: not too high, and not too low. They have some autonomy and some authority, but all that is owed to the fact that they are enacting the will of their boss. Depending on the organization, their title might be Manager or Director. In government, this might be the highest career staffer that is not appointed by elected officials. In a corporation, they might have a high salary, but their stock options, if they have them, will not make them independently wealthy. While seen as high up the chain by folks at the bottom, they earn their salary through 24x7x365 work and do not have a golden parachute.

Landed Gentry

Gentry were landowners who could live on rental income they earned from their country estate. They have land, but don’t work it directly. They might work in the town as a lawyer, but they don’t have to work to earn money to live because of the money they earn from their property. This status continued after medieval times and describes almost all of the signatories of the Declaration of Independence.

These people occupy all sorts of roles in your organization, but only roles in the middle, where life is pretty easy, hiding in plain sight. Nice, cushy, corporate jobs. If you don’t have to put on the headset and work in the call center to make rent, you’re not gonna do it. These folks are not likely trust fund babies who were born rich, but made their money by working, saving, maybe making a killing with stocks, and almost always through buying a house (or several houses) before Gen Z was born. Now that house is worth a ton and out of reach for people who have the same jobs today they had when they bought the house way back when. If things get tough, they can resign or get laid off and just “take time to live, you know?” If you are a part of Gen Z, you are entitled to hate this person, no matter how nice and cheery they are.

Bailiff

The bailiffs of manors collected fines and rents, and served as accountants. They were in charge of the land and buildings on the estate. They had to keep the operation running smoothly, as the lord could look out his window and see the results of their labor.

This is a role that involves constant interaction with people actually doing work, without doing much actual “work.” The work they do is all about checking up on workers and nitpicking them, their work, and enforcing paperwork compliance. Someone with the Project Manager title but limited real power is a good parallel for a bailiff. On software development teams, this is the Scrum Master, the person who assigns tasks or user stories for completion.

Reeve

The manorial reeve was one of the most familiar officials for most peasants, who might only occasionally see the Lord and Lady. He organized the details of daily work of the manor. If you’ve ever seen a movie with a reeve character in it, he is mean, vindictive, and cruel. Everybody hates him.

This is the lowest rung of people management, with limited real power. They probably have “supervisor” in their title. Previously, this person has most likely done the job of the people they now supervise. Their team might be hourly or shift workers. Think of a call center team lead or an assistant manager at a chain restaurant. The guy holding the clipboard while the other guys do the hard manual labor. This role has low status in the overall corporate structure, but has the power to make life bearable or miserable for those at the bottom of the chain.

Peasant

The medieval world had three classes of peasants: freeman, serf, and slave.

Freeman / churl / housecarl

A freeman or free tenant had achieved freedom from the lord of the manor and so could live and work wherever he chose. They were subject to fewer laws and restrictions than serfs. They are not noble, and while they might have a few silver coins in their pocket, they don’t earn wealth from an estate. They have to work to make a living.

As all are free people today, this can be confusing in a corporate context. The best analogy is someone who is not tied to their current job because their skills are so in-demand. A software engineer who receives unsolicited offers from random recruiters every week is a good parallel. Someone who has worked for the same company for more than ten years and might struggle to find their next job is not. Freedom now means freedom of choice in the work that you do.

Serf / villein

Most peasants were serfs. Most people were serfs. If any of your ancestors were from Europe, they were almost certainly serfs. A serf was a legally unfree person, forbidden to leave the lord’s land and required to perform labor for their lord. But they weren’t exactly slaves. Serfs had a legal right to have a family, and their labor requirements were limited to a predetermined amount of time. Serfs owed their lord all kinds of fees, even in death. When a serf died, the family would owe the lord a tax, usually an animal, to pay the lord back for no longer having the labor of the dead serf. Seriously! That’s a true fact, even if it’s depressing.

Almost everyone was a serf then, and most are serfs now. Folks get the Sunday scaries before the workweek starts, knowing it’s another week of the grind. You trudge in on Monday morning and try to do your best to make it through. Some enjoy their work. Others hate it. You watch the clock on Friday and forget all your action items and outstanding deliverables as soon as you’re out the doors for the weekend. You make merry with our fellow serfs after work and keep coming back to support your family. Except the Monday after the Super Bowl. Everyone calls in sick then, even though the boss knows they’re just hungover. Sometimes it’s not so bad being a corporate serf.

Slave

With the decline of the Roman empire in the west, slavery died out and evolved into serfdom. Why this happened is a debate among historians. Either as the population Christianized, and holding coreligionists in bondage became unseemly, or it was purely economic, with it being cheaper for landowners to demand labor from unfree serfs rather than provide necessities for living to slaves. Although slavery was relatively rare in Western Europe, the practice of slavery didn’t go away. Criminals and wartime captives were sometimes enslaved. Owning slaves was more common in the east. The Vikings made half their fortune from the slave trade. The Byzantine and Islamic empires were the primary buyers of the Viking’s enslaved captives. Eunuchs were castrated slaves who sometimes held high positions in court, and they were found throughout the east, from Constantinople to Baghdad to China.

Although illegal today, slavery still exists in debt bondage and human trafficking, among other horrors. Thankfully, no matter how bad corporate jobs are today, no corporate drone is literally a slave. If your employer is breaking labor laws, please call the cops.

Townspeople

The village attached to a manor was the idealized form of the three estates model of medieval life. In these small villages, everyone fit neatly into the categories of noble, clergy, or peasant. Town life was a bit different. People who lived in a medieval town were still peasants, but with more flexibility than their rural counterparts, able to generate wealth and achieve much more social mobility. If a serf ran away to a town and lived there for a year, of course working in the absolutely worst jobs, then they would earn their freedom from their lord. Tradesmen were strictly regulated by the charters of their guilds.

Today there are legions of people who work at an organization but technically are not in the organization. These are the contractors. They drink the same coffee in the same breakroom, but their ID badges (and sometimes even their company emails) clearly identify them as insider-outsiders. They get no protection from the lord, as they are the first to be laid off. They owe no loyalty to the lord. Their real loyalty is to the consulting firm that actually employs them, kinda like a guild. These guys exist in the corporate hierarchy, but they’re not exactly a part of the permanent structure.