Starting as a web designer at Black Isle Studiosin 1999, he quickly worked his way up the ladder to an associate designer position and then lead designer on Icewind Dale II. While at Black Isle he was known for coming up with the "Ex-Presidents" project naming system. In November 2003 Sawyer announced his departure from Black Isle, where he had been serving as lead designer of Fallout 3, to pursue other projects. Interplay went on to close Black Isle two weeks after Sawyer's departure. On July 19, 2005, GameSpot reported that he had left Midway's ', and was accepting a position at Obsidian Entertainment, a studio founded and staffed by many veterans of Black Isle. His first role was as the lead designer for Neverwinter Nights 2. He later acted as the project director and lead designer of '. In December 2011 Sawyer publicly released a New Vegas mod designed for his own personal use adding a large variety of small tweaks to the game ranging from rebalancing the karma of certain characters to slowing down the level up speed. As of November 2012, this mod is up to version 5.1 which was released in September 2012. He also served as the project director and lead designer on the Aliens RPG. Sega, the game's planned publisher, subsequently canceled the project resulting in layoffs at Obsidian. According to Obsidian CEO Feargus Urquhart, the game - titled Aliens: Crucible - "looked and felt like it was ready to ship". In 2012, with Obsidian on the brink of financial disaster after the cancellation of another project by a publisher, Sawyer proposed the company return to its design roots by making an isometric RPG in the style of those created at Black Isle. Arguing there was a market for this type of game among fans, Sawyer suggested turning to the platform Kickstarter to secure funding for development without a publisher. He succeeded in persuading company leadership, and the game, Pillars of Eternity, met its Kickstarter funding goal of 1.1 million dollars in 27 hours. It ultimately raised nearly four million dollars, setting a Kickstarter record at the time. Sawyer later served as the director and narrative designer on its sequel, , which was also crowdfunded and released in 2018.