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He moved to Seattle after graduating from college and worked his way into Wizards of the Coast's sales department. Jacobs has been the developer, lead designer, and sometimes cartographer on projects for Bastion Press, Green Ronin Publishing, Wizards of the Coast, and Paizo. Jacobs has authored and co-authored several other products for the Dungeons & Dragons fantasy roleplaying game, including Dungeon Master's Guide II, Lords of Madness, Frostburn, and Red Hand of Doom. He also wrote Fiendish Codex I: Hordes of the Abyss with fellow Paizo editor Erik Mona. Jacobs and Erik Mona co-wrote Expedition to the Ruins of Greyhawk (2007), a 3rd edition D&D remake of Greyhawk Ruins (1990).

Jacobs has worked as the associate editor, and later the managing editor of Dungeon magazine. In the 2000s, Jacobs served as the editor-in-chief of Dungeon magazine, published by Paizo Publishing. Jacobs described himself as "one of the chief architects" of the Dungeon Adventure Paths, in addition to working on all the other adventures published in the magazine. Jacobs became the Editor in Chief for Dungeon magazine in June 2006. Jacobs is the Creative Director for the Pathfinder Adventure Paths-focused monthly publication from Paizo. He also wrote "Burnt Offerings", the adventure featured in Pathfinder: Rise of the Runelords #1.

Jacobs has been involved in the role-playing industry since the age of sixteen, when his adventure "Scepter of the Underworld" was published in Dungeon #12 in 1988. Jacobs grew up in Point Arena, California, and went to college at the University of California, Davis.