Militarist - Free Sword (Grim Hollow)

 Free Swords are commonly referred to as
mercenaries, taking jobs that the local forces
can’t handle. Mercenaries may be the only
hope of villages looking for defenders against
raiders, overextended sheriffs chasing powerful
fugitives, and small merchants traveling Etharis's
dangerous byroads. Larger mercenary companies
win wars on behalf of cities and kings. They fight
for coin above all else, exacting little honor from
the contracts they accept.

Rank 1 - Hireling

You have been trained in combat by a group of
mercenaries with a Free Sword licence. After
many tedious years of combat drills and shooting
at straw targets, you are close to receiving your
very own license.

Holdings:

Lodging at any Free Sword’s guild house and use
of Free Sword’s training grounds and facilities.
The contract for a dangerous bounty that your
mentor died trying to complete.

Progression:

Complete a contract with a guild member who has
a Free Sword licence.

Rank 2 - Sellsword

After proving your competence and
trustworthiness, you have become a guildlicensed
Sellsword. You start to receive specific
requests for jobs as your reputation grows.

Holdings:

A Free Sword licence, which allows you to accept
your own contracts as a mercenary and collect
the rewards.
Access to hirelings belonging to the Free Swords
guild, who you can contract for a small fee.Progression:
Lead a team successfully through several highstakes
encounters during mercenary contracts.

Rank 3 - Sword Commander

You have proven your combat prowess and
command of battlefield tactics. Special requests
for your services are becoming more frequent,
often from people or groups of higher social
status. The mercenary companions who
accompany you on your jobs have matured
into disciplined soldiers who trust you as their commander.

Holdings:

Your own private room in a guild house and a
retainer who can either take care of business
for you at the guild house or accompany you on
your travels.
Command authority over lower ranks and the
power to employ them for jobs.
Access to restricted jobs that depend on sensitive
information or extraordinary risk.

Progression:

Successfully complete a restricted job for a highprofile
client.

Rank 4 - Battlelord

You have been elected by the members of your
Free Swords guild to lead them forward to greater
power and acclaim. What type of commander are
you going to be? Will you lead by example and
rush into the fray during combat, or retire the
sword and pick up the pen?

Holdings:

Command of the Free Sword’s guild and its
members, including managing contracts, and
overseeing the training of hirelings.
A guild chapterhouse, which includes housing for
you and your lieutenants as well as an extensive
armoury for guild members.

Astute Intuition

Whenever you make a Wisdom (Insight) check
while trying to detect a lie from Aristocrats,
Criminals, or Common Folk, you can add your
Profession Die to the roll.

Applied Leverage 

When you make a Strength
(Athletics) check to force open a door or container,
you may add your profession die to the roll.

Beast Whisperer

Whenever you make a Wisdom (Animal Handling)
check to train or direct orders to a beast, you can
add your Profession Die to the roll.

Born in the Saddle

Whenever you make a Wisdom (Animal Handling)
check while riding an animal or interacting with
your mount, you can add your Profession Die
to the roll.

Bounty Hunter

Whenever you make a Wisdom (Survival) to track
Criminals, you can add your Profession Die

Calloused Hands

Whenever you make a Strength (Athletics) check
to lift, drag, or shove a heavy object, you can add
your Profession Die to the roll.

Copycat

Whenever you make an Intelligence or
Intelligence (Forgery Kit) check to forge or create
a document, you can add your Profession Die
to the roll.

Disciplinarian

Whenever you make a Charisma (Intimidation)
check while issuing a command to an individual
of lower rank within your background, you can
add your Profession Die to the roll.

Drunkard

Whenever you make a Constitution check to
determine if you will throw up, pass out, or how
severe a hangover is, you can add your Profession
Die to the roll.

Figure of Authority

Whenever you make a Charisma (Persuasion)
check while interacting with Common Folk, you
may add your Profession Die to the roll.

Forecaster

Whenever you make a Wisdom (Survival) check to
determine the weather for the next 48 hours, you
can add your Profession Die to the roll.

Gambler

Whenever you make a Dexterity (Sleight of Hand)
or Wisdom (Perception) check to cheat at a game
or catch someone else cheating, you can add your
Profession Die to the roll.

Hard-Working

Whenever you make a Constitution check for a
repetitive task such as marching or labouring for
hours without rest, you can add your Profession
Die to the roll.

Interrogator

Whenever you make a Charisma (Intimidation)
check to extract information from an enemy who
is restrained, you can add your Profession Die
to the roll.

Looter

When you make an Intelligence (Investigation)
roll to find hidden valuables, you may add your
profession die to the roll. 

Menacing Presence

Whenever you make a Charisma (Intimidation)
check, and are interacting with Academics,
Common Folk, or Seafarers, you can add your
Profession Die to the roll.

Navigator

Whenever you make a vehicle check, you can add
your Profession Die to the roll.

Passionate Orator

Whenever you make a Charisma (Performance)
check to influence an Academic, Military, or
Clergy member, you can add your Profession Die
to the roll

Recruiter

Whenever you make a Charisma (Persuasion)
check to recruit people into a role, you can add
your Profession Die to the roll.

Renowned

Whenever you make a Charisma (Persuasion)
check, and are interacting with Military,
Outlanders, or Criminals, you may add your
Profession Die.

Sentry

Whenever you make a Wisdom (Perception) check
while on watch duty or defending a fortification,
you can add your Profession Die to the roll.

Shrewd Deduction

Whenever you make an Intelligence
(Investigation) check to investigate a crime scene,
you can add your Profession Die to the roll.

Urban Sprinter

Whenever you make a Strength (Athletics) or
Dexterity (Acrobatics) check while running away
from a pursuer, or pursuing someone else, you
can add your Profession Die to the roll.

Wayfarer

Whenever you make a Wisdom (Survival) check to
find a path or avoid getting lost, you can add your
Profession Die to the roll.