Skip to main content


Whether it came from army training, time with a mercenary band, a military education, or some less-conventional source, you’ve been taught the art of war. Battle is far more than just swinging a sword, after all, and you likely spend as much time with tactical manuals and maps as you do conventional weapons.

Where did you gain this level of tactical ability? Do you hire your skills out to the highest bidder or did you take jobs on moral grounds? Or do you just seek out excitement and adventure to test your skills?

Ability Score Increases: +1 to Strength or Dexterity, and +1 to Intelligence or Wisdom.

Skill Proficiencies: Engineering and Survival.

Tool Proficiencies: One type of artisan’s tools and one gaming set.

Suggested Equipment (Cost 15 gold): Traveler’s clothes, ink (1-ounce bottle), ink pen, mess tin, 10 sheets of parchment, a signal whistle.

Feature: Strategic Eye. Focusing on the tactical aspects of fighting can push combatants in different directions. Choose one of the following options.

Always Ready. Years of studying opponents have prepared you for any fight. As long as you can see or hear your foe you gain an expertise die on initiative rolls.

Studied Readiness. Your strategy in combat extends beyond one-on-one encounters. If you are familiar with an area (whether through studying maps or if you’ve been in the area before), then you roll initiative with advantage whenever in that area. Alternatively, you can choose to roll initiative with disadvantage to grant one ally the ability to roll with advantage in that same area. The level of familiarity or study required to use this feature in a given area is determined by the Narrator.

Adventures and Advancement. With such a talent for combat strategy, you may eventually catch the eye of a military or group of mercenaries interested in hiring you for your services. If you take these jobs, you and your party will earn more than others would doing the same work. Eventually, if you continue to complete tasks for them, wealthier patrons may seek you out for even larger engagements and provide you and your companions a wealthy lifestyle.

Connection and Memento. Roll 1d10, choose, or make up your own.

Strategist Connections

  1. The retired military officer who taught you the basics.
  2. The school rival who you competed with both physically and intellectually.
  3. The mercenary commander you impressed when you defeated two of their men in a street fight.
  4. The drunkard you defeated one night in a tavern, who turned out to be an officer’s son.
  5. The instructor who said you wouldn’t amount to anything.
  6. The officer who tried to recruit you for a military group that you joined or turned down.
  7. The blacksmith who always repaired your damaged weapons.
  8. Your childhood friend who supported your dreams of going to the academy.
  9. The leader of a group of bandits that you lured into a trap to save your village.
  10. The shady military recruiter who convinced you to sign up with promises of wealth and fame.

Strategist Mementos

  1. An antique military emblem a teacher gave you long ago.
  2. A book on combat strategy.
  3. A notebook full of ambush stratedgies.
  4. Your old academy uniform.
  5. A copy of your graduation papers from the academy.
  7. A map of the settlement you grew up in and the surrounding areas, heavily marked up with notes on strategic points.
  8. A broken weapon you used against a more experienced opponent.
  9. A letter from your childhood friend after you left home.
  10. A scar from a battle that went wrong.