She was a foundational member of The Forge, an early leader in the indie role-playing game movement and is considered the creator of the American Freeform genre of roleplaying games, which combine indie RPG principles and mechanics with Nordic freeform and American chamber live action role-playing techniques.

[3] She credits talking with other users at the Forge Forums during the early 2000s with helping her to get involved in design and self-publishing.

Baker-Care or Baker-Boss Principle), which states, "System (including but not limited to 'the rules') is defined as the means by which the group agrees to imagined events during play."

[6] She also coined the concept of "bleed" at Ropecon 2007 and defined it as the emotional transfer between player and character, in either direction, during a role-playing game.

[17] Bubblegumshoe, a Gumshoe System Teen Noir setting, written with Ken Hite and Lisa J. Steele, won the 2017 Gold ENnie Award for Best Family Game.

[23] Boss resides in Greenfield, Massachusetts[24] and is married to fellow game designer Epidiah Ravachol, creator of Dread.