Highwayman

A highwayman is much akin to an ordinary robber but with a specialty in quick, decisive strikes to mobile targets. Highwaymen have to be tough combatants because their stealth and subterfuge happen before a job ever starts. Ranged weaponry and mounts are important tools of the trade for a highwayman since their typical quarry is often more than capable of running away, should the need arise.

Level 3: Tools of the trade

You gain proficiency with Martial ranged weapons, including firearms, as well as proficiency with a Disguise Kit.

Level 3: Natural Born Rider

Due to needing to catch moving targets so often, you have become adept at riding any number of mounts giving you the following benefits. 

Cunning Rider. You have advantage on checks to avoid being knocked off of a mount and can use your Cunning Action Dash or Disengage while mounted, conferring the benefits to the mount as well.

Animal Whisperer. You gain proficiency with Animal Handling, allowing you to pilfer mounts more easily.

Level 9: Crack Shot

You gain the following Cunning Strike options.

Ricochet (Cost: 1d6). After dealing damage to a creature with a ranged weapon attack, you may use the same attack roll against another creature within 10 feet of the target. On a hit, the target takes the weapon attack damage only, without any Sneak Attack or the ability modifier.

Level 13: Roving Rake

Being on the run has allowed you to become adapted to all forms of environments. You gain the following benefits:

All-Terrain Escape Artist. You gain a Climb and Swim speed equal to your Speed. Additionally, you ignore nonmagical Difficult Terrain, including while mounted.

Lay Low. You and a number of creatures of your choice equal to your proficiency bonus gain a bonus equal to your proficiency bonus and advantage on Stealth skill checks while they are within 30 feet of you.

Level 17: Headshot

Once per day, when you hit a creature and add Sneak Attack to the attack, you can double the amount of sneak attack dice that you roll. When you use this feature, treat any rolls of 1 or 2 on the Sneak Attack damage as a 3.