Catchpole

Catchpoles either operate as part of a town guard, or might act as the only real peacekeeping in a small community. The catchpole can perform the normal duties of a town guardsman, but has the more specific function of chasing down petty criminals, or in some cases even, tax cheats depending on the jurisdiction. Catchpoles aren't really the scourge of professional criminals, more like the scourge of local kids skipping their chores.

          Adventurers, even the most docile ones, have a tendency to upset law enforcement occasionally - and more than one catchpole has been called to respond to some strange incident outside of a local tavern, only to discover the shenanigans of adventurers, and to sometimes be drawn into them. Catchpoles are likely to look for opportunities to track down tougher criminals, since in their profession they never really had the opportunity to.

          Master of the Chase: As a catchpole, you are an expert at chasing down thugs and troublemakers. As a result, if you are ever participating in a Skill Challenge to Chase someone or something, you add 1 automatic success at the start of the challenge. Furthermore, on a critical success, you add 3 successes, and on a critical failure, you only add 1 failure. When you are on your own and when rolling an Athletics or Acrobatics check to chase, you have advantage.

If you choose Catchpole, you gain the following:

~Either a +1 to your Wisdom score or a +1 to your Dexterity score~

~A Skill Proficiency in either Athletics or Acrobatics~

~Any one Language spoken in your jurisdiction~

~The following items: The seal of your liege, a club, manacles, a sweat-stained tunic, and a belt purse with 10sp~

~Master of the Chase feat~

Coin-Stamper

Alternatively: Coiner.

Coin-Stampers are a kind of specialist metallurgist who take thin slabs of gold, silver, copper or other precious metals, cut them into small shapes and 'mint them' with an official seal provided by the government. These seals tend to carry a mark of the liege lord, often his visage, or might have words or other symbols. Minting coinage is a way to spread legitimacy in the eyes of your own people, while also granting the government's backing behind the value of the coinage. Debasement, the practice of mixing in cheaper metals into a coin is never publicly acknowledged, but in reality coiners are often ordered to do so by desperate governments. Coiners are watched diligently by their overseers, and the act of stealing any scraps of precious metal from the government is almost always punished by death, as it is considered treason.

          Coin-Stampers tend to spend all their days locked up in windowless rooms minting coinage, so when they do rub shoulders with adventurers, it's usually a bad sign. Adventurers who are former-coiners are often very handy when it comes to inspecting any currency the party comes across, and seeing to what degree it has been debased - they might also draw conclusions on the history of a tomb based on the mintage of the coins therein.

          Custom Coinage: Coins are normally stamped with the image of a leader or ruler and are traditionally minted to bestow glory and honor upon the barer of the image. You possess the ability to restrike old coins with a new image, which requires 8 hours of hard work. You can use these coins for one of two purposes, either strike them with an image representing your party, or strike them with the image of someone the party is trying to gain sway with. If the coins are struck with the party's image, they will generate notoriety for the party, and increase the chance that the average person knows of the party's endeavors. If the coins are struck with the image of someone the party is trying to gain sway with, and are given as a gift to them, that person will view the party with favor. Keep in mind, rulers who discover the party has restruck their own coins will likely react poorly (it is technically treason). Depending on the type of person, the number of coins required to flatter them will change dramatically. 

         Peasant: 1cp

         Freeman: 5cp

         Merchant: 1sp or 10cp

         Faction Leader, Mayor, Reeve: 1gp, 2ep, 10sp, or 100cp

         Baron, Count, or Bishop: 1pp, 10gp, 20ep, or 1,00sp

         Duke: 10pp, 100gp, 200ep, or 1,000sp

         King: 100pp, 1,000gp, or 2,000ep

         Emperor: 500pp or 5,000gp

If you choose Coin-Stamper, you gain the following:

~Either a +1 to your Dexterity score or a +1 to your Intelligence score~

~A Skill Proficiency in either Investigation or History~

~A Tool Proficiency with Smith's tools~

~The following items: A set of coin stamps, smith's tools, a small chest of 50 unstamped silver coins, leather gloves, and a belt purse with 10sp~

~Custom Coinage feat~

Constable

Alternatively: Town Guard, Town Watch, or Bailiff.

Constables are the peacekeepers in settlements and towns, and occasionally even in keeps and other areas. They tend to work locally, often patrolling a specific route, and often no more than a few town blocks. They might also guard a single building, preventing important government buildings from being infiltrated. Constables and town guards work for local governments, and may range from a few disorganized guards, all the way to massive organizations with multiple ranks and thousands of members.

          Constables might often do their work exactly because they want to promote law and peace in a chaotic and unjust world, but often the work of constables can either be pretty mundane, or at its worst, corrupt. So, often constables find themselves drawn towards a life of adventure as a way to make a bigger effect on the world, and really live up to their goals. 

          Non-Lethal Force: As a constable, you were taught how to bring in a dangerous criminal without killing them, though some of your colleagues never quite picked up the ability, so you were used to having to tell them what to do with perps. When you or an ally would deal damage with a purely lethal attack that reduces an opponent to 0 hit points, as a reaction, you grant that person the knowledge they need to merely knock the person out instead (normally, only melee attacks can knock a foe out).

If you choose Constable, you gain the following:

~Either a +1 to your Strength score or a +1 to your Wisdom score~

~A Skill Proficiency in either Perception or Insight~

~A Tool Proficiency with any one Gaming Set~

~The following items: A lucky helmet, padded armor, a spear, a seal of the watch, and a belt purse with 12sp~

~Non-Lethal Force feat~

Courier

Alternatively: Messenger or Pigeon Trainer.

Couriers are runners who carry messages, letters, packages, or information from point a to point b. Often, this can be across a government complex or across a town, but often it can be between towns, from one side of a kingdom to another, or even across whole continents. In a time before any organized postal service, individual couriers are the only way to mundanely communicate over great distances. Some nations organize messenger posts, one messenger carrying the message to a post, which immediately passes it on to the next, allowing the message to be carried forward without any breaks. While sometimes unreliable, couriers might also employ animals, in particular carrier pigeons or carrier birds. They usually work for a government, but sometimes work as private couriers for individuals.

          Couriers might sometimes bite off more than they can chew with a job, particularly if it means crossing through dangerous territory - in these cases, they might travel alongside tough adventurers to keep them safe, and even pick up a few tricks along the way. Couriers who turn to a life of adventure might constantly try to work out shortcuts to get to their goal more quickly, or take safer routes to avoid undue trouble on the road.

          Carrier Birds: As a courier, you raised birds bred to be message carriers. You have 5 birds in your possession (you may choose between pigeons, crows, or starlings). Each of them has a roost in a town or holding of your choice, and at a moment's notice, you may send a message with them, and they shall travel to that location directly at a speed of 60 miles per hour for up to 10 hours a day. Additionally, if a bird spends 5 days in a new roost, it will consider that its new home. Birds once at their roost have to be retrieved in person, and won't know where to find their trainer. Furthermore, you can always train more birds. Taming a wild carrier bird requires a DC 15 Animal Handling check.

If you choose Courier, you gain the following:

~Either a +1 to your Constitution score or a +1 to your Wisdom score~

~A Skill Proficiency in either Animal Handling or Athletics~

~A Tool Proficiency with either Vehicles (Land) or Vehicles (Water)~

~The following items: 5 birds and their cage, a riding horse or pony or rowboat, the seal of your liege, a woolen cloak, and a belt pouch with 10sp~

~Carrier Birds feat~

Diplomat

Alternatively: Emissary or Ambassador.

A diplomat tends to be a fairly important position usually filled by highborn subjects with great skill in reading, writing, and oratory. Diplomats are sent by a sovereign or state to represent that sovereign or state in negotiations with another entity, usually another nation, but sometimes independent towns, or even simply private organizations. Diplomats tend to work closely with the ruling powers, and might have ambitions to rise further in the state bureaucracy. 

          Diplomats, while normally treating with other diplomats and governors, sometimes are tasked with contacting and hiring out adventuring parties on behalf of their liege. Sometimes, they might even travel with them for a time, to ensure they actually do what they've been tasked to do. Adventurers who used to be diplomats will use their knowledge of court politics and diplomatic proceedings to ensure the party always makes a good impression with anyone they entreat with, particularly representatives of the powers that be.

          Culturally Fluent: You are adept at preparing to culturally engage with those of a different culture than yours. At the beginning of the day, you must choose a culture that you prepare to engage with that day. Then, you get a reroll on any Persuasion or Deception check with a member of that culture, but only one reroll for the whole day, and you must keep the new roll.

If you choose Diplomat, you gain the following:

~Either a +1 to your Charisma score or a +1 to your Intelligence score~

~A Skill Proficiency in either Persuasion or History~

~Any one primary Language of a nation or faction in Adra~

~The following items: The seal of your liege, 10 pieces of parchment, a quill and ink, fine clothes, and a purse with 20sp~

~Culturally Fluent feat~

Executioner

When a lord or government believes a criminal is irredeemable, they will sentence them to death. The prevalence of executions varies greatly by region in Adra, but in almost all places, folks regardless of their beliefs surrounding capital punishment, tend to keep the men and women that carry out the act at arms length, and executioners usually live outside of the communities they work with, if not for social stigma, if also because they don't want to live near the families of the convicts they are tasked with killing.

          Executioners tend to have spotty relationships with other adventurers - at times, parties will feel that only death will bring certain villains to justice, while at other times, parties feel a fairly banal crime has sent someone unjustly to the chopping block. Whether through friendship or guilt, occasionally these executioners find themselves travelling with the parties they encounter. Adventurers who used to be executioners will probably give great care to how the party deals with killing - rather than wildly killing any enemies they encounter, on the contrary, a professional executioner believes that death should only be met out coolly, with virtuous intent and just methods.

          Death Throws: You are well accustomed to the sight of someone that is about to die. You can tell when a creature is at or below 25% of its hit points total, or when a creature has fallen unconscious or is dead. Telling either of these requires a bonus action or action to assess the damage.

If you choose Executioner, you gain the following:

~Either a +1 to your Constitution score or a +1 to your Strength score~

~A Skill Proficiency in either Medicine or Performance~

~A Tool Proficiency with a Poisoner's kit~

~The following items: An executioner's axe (too unwieldy to use in battle), 20ft of hempen rope, a poisoner's kit, a black hood, and a belt pouch with 15sp~

~Death Throws feat~

Reeve

Alternatively: Administrator.

Reeves are government officials which are assigned to administer to a hamlet, fiefdom, village, or some similar allocation of land and people. Unlike lords or elected officials, they technically don't rule the land or control it themself - instead, they act on behalf of their ruler in "administering" to the land. Still, the line between ruler and reeve is often blurred, and to the peasants that work in their lands, reeves often seem like lords to them.

          Reeves often oversee small or insignificant holdings, and as such, they might not have the resources to deal with major problems, like a wandering monster. As such, they commonly resort to dealing with adventurers and other sorts of mercenaries to deal with threats to their jurisdiction. When Reeves are done with their work and are recalled to be replaced with someone else, they might decide to take up the work of an adventurer as a change. Reeves who become adventurers are likely to look for ways that the adventurers can help in more subtle ways, by advising officials dealing with problems rather than just acting as their bagmen.

          Benevolent Bureaucrat: You are experienced at dealing with the everyday logistics of running a small government. You use this experience to maximize a group's budget when hiring others. You can hire two hirelings for the price of one instead, or hire them for twice as long, but not both.

If you choose Reeve, you gain the following:

~Either a +1 to your Intelligence score or a +1 to your Charisma score~

~A Skill Proficiency in either History or Persuasion~

~A Tool Proficiency with a Dragonchess set~

~The following items: The seal of your office, the logbook from your time in office, a dragonchess set, a fine hat, and a purse with 15sp~

~Benevolent Bureaucrat feat~

Secretary

Alternatively: Clerk.

For the civil bureaucracies of labyrinthine governments, or the complex hierarchies of private organizations, there is constant note taking, record keeping, and visitor histories that needs to be done and constantly updated. Given what literacy rates are in a medieval society, those that are able to read and write clearly and quickly already possess a valuable skill set. Secretaries make up the network that connects various governmental bodies together, and keeps these bureaucracies chugging along.

          Secretaries tend to be fairly intelligent folks, who do a pretty menial job. As such, they might sometimes be drawn to apply their unique talents to something a little more exciting. Adventurers who used to work as clerks or secretaries are often very thorough in keeping records of the party's adventures, as well as their possessions, contacts, and goals.

          Master Multitasker: You are used to having to read and write at the same time, all while conversing with someone at your desk. Your multitasking allows you to gain a Use Object action as a free action. You may do this once per short rest.

If you choose Secretary, you gain the following:

~Either a +1 to your Intelligence score or a +1 to your Charisma score~

~A Skill Proficiency in either Investigation or Persuasion~

~A Tool Proficiency with Calligrapher's supplies~

~The following items: A logbook, a quill and ink, the seal of your office, a chaperon (fancy hat), and a purse with 15sp~

~Master Multitasker feat~

Sheriff

Alternatively: Detective or Investigator.

Sheriffs are singular figures of authority within systems of law and order - they tend to serve over a large jurisdiction, often an entire barony or county, and they tend to work under the direct authority of a member of the ruling order, rather than working in a separate hierarchy of their own. They can often be viewed as protectors and guardians of vulnerable communities, but can sometimes garner a reputation as corrupt thugs that can't be held accountable for their actions.

          Sheriffs not only often work with adventurers in tracking down particularly pernicious villains, they sometimes decide to give up their work as civil servants and take up with adventuring permanently, viewing it as an avenue to possibly do more good overall in the end. Sheriffs who become adventurers are likely to have hard lines they won't cross, and procedures they follow when they come up against humanoid villains.

          That's Odd: When you enter a new location, such as a room or corridor, you immediately notice one thing out of the ordinary. The DM determines what it is, or whether there's nothing reasonable to pick up, skipping obvious clues that can be easily noticed without a check or specifically looking for them. You learn only that an area or object is suspicious, but not why it's suspicious. For example, if you entered a study with a large bloodstain on the ground, the bloodstain is so obviously suspicious that it's evident to you already, so the DM might note that there's something suspicious about the desk drawer instead. You would then need to investigate the drawer further to find out what specifically is out of the ordinary. That's Odd doesn't reveal whether creatures are suspicious. You don't typically get any benefit when you leave and come back to a place, though if a major change has happened there and time has passed, the GM might determine that you do.

If you choose Sheriff, you gain the following:

~Either a +1 to your Wisdom score or a +1 to your Strength score~

~A Skill Proficiency in either Investigation or Intimidation~

~A Tool Proficiency with Land Vehicles~

~The following items: The seal of your office, a simple weapon of your choice, studded leather armor, a cool black hat, and a belt purse with 15sp~

~That's Odd feat~

Spy

Spies are agents sent by a sovereign or other agency in order to gather information on another faction. Usually, their work is fairly mundane, setting up shop in the town or location of interest, and slowly putting out feelers for information. In rare cases, the most skilled of spies might go "deep-cover", infiltrating an organization directly, at great risk to their life and limb.

          Spies live a life of adventure if anyone did, travelling to far away lands, gathering government secrets, and occasionally fighting for their life if they get caught. Spies sometimes might inadvertently discover that they are working on the same job that a group of adventurers are, and they might even work together to accomplish their goals. Spies who turn to a life of adventure will tend to lean towards quests that are in cities, and hopefully that involve a good deal of intrigue - they might even use adventuring as a cover for their continued service to their liege.

          Wall Fly: In the gathering places of the world, taverns, marketplaces, temples, etc., there is always something being whispered, or perhaps shouted, that is useful to the right person. You can spend two hours, and 2d12 copper pieces in a public gathering space (representing buying drinks, or making purchases, etc.), and you will receive a useful piece of information that pertains to one of your own or one of your group's goals. The DM determines what the information is exactly, but generally speaking, there is an 80% chance of it being a minor piece of information, and a 20% chance of it being a major piece of information. You can use Wall Fly once per long rest.

If you choose Spy, you gain the following:

~Either a +1 to your Wisdom score or a +1 to your Dexterity score~

~A Skill Proficiency in either Perception or Stealth~

~A Tool Proficiency with a Disguise kit~

~The following items: A disguise kit, a dagger, a letter with the last orders you were given, unassuming clothing, a belt pouch with 15sp~

~Wall Fly feat~

Tax Collector

Alternatively: Tax Farmer.

Tax Collectors have never been popular in history - never more so than in the medieval period, largely removed from concepts of patriotism or social services, taxes in a medieval world might just feel like getting shaken down for your lunch money by some lord you'll never meet. Tax collectors have to be quick thinking and forceful, and at their worst, brutal. Still, some tax collectors in local communities may let locals who can't afford it off on paying. Tax collectors tend to work as civil servants, though can in some cases work for private firms contracted with the government, an infamous practice known as tax farming.

          Tax collectors often meet adventurers, and discover that more than anyone, they don't usually like paying taxes - they have a habit of getting out of paying them in fact. Still, in trying to track them down, sometimes friendships form, and a new adventurer is accidentally born. Adventurers who were once tax collectors tend to by nature look towards local governors and officials for work rather than private individuals, and they are rarely going to work with criminals - after all, criminals don't pay their taxes.

          Free Parking: You know the lingo, proofs, and signs of tax collecting. If you are ever approached by a tax agent, for any reason, you have a 66% chance (4 in 6) of avoiding paying the tax (and this can extend to your group's behalf). Furthermore, even if you fail to avoid it using this feature, you may still attempt to persuade the tax agents using normal means. A tax agent could mean a tax collector, a treasurer, a toll keeper, or any government official collecting any sort of normal, everyday fee (not including abnormal fees, or that the party seeks out as payment for a service by the government).

If you choose Tax Collector, you gain the following:

~Either a +1 to your Intelligence score or a +1 to your Charisma score~

~A Skill Proficiency in either Intimidation or Persuasion~

~Any one Language spoken in your jurisdiction~

~The following items: The seal of your liege, a club, manacles, a sweat-stained tunic, and a belt purse with 10sp~

~Free Parking feat~

Town Crier

Town Criers are the folks tasked with spreading information to the masses. They can sometimes act independently, keeping their ear to the ground and calling out the news they hear in exchange for a private wage, or they more often might be told specifically what information to spread by a governor or private organization. Often, town criers are the only official way to hear the news, and are really useful for those who pass quickly from one town to the next.

          Town Criers are often an important tool for adventurers trying to keep their ears to the ground, and they might sometimes ask town criers more questions about what's going on in particular, even when they might not know the answer. Town criers who become adventurers never quite kick the habit of looking for the local news, and might sometimes offer news from another land as a way to gain favor or make some quick money.

          Ear to the Ground: You are attuned to the stories and major events going on in the world. Once every week (on Highday, the news day) you receive the biggest piece of news in either the world, the nation, or the town, as determined by the DM. At some point in the week, you would have needed to be in a population center for this feat to work.

If you choose Town Crier, you gain the following:

~Either a +1 to your Charisma score or a +1 to your Wisdom score~

~A Skill Proficiency in either Performance or Perception~

~A Tool Proficiency with a Horn~

~The following items: A horn, a bell, a parchment with recent news, a cap with a feather, and a coin purse with 10sp~

~Ear to the Ground feat~