Some of his best known roles include Spider-Man in Marvel's Spider-Man and various Marvel media, Mike, Orbulon and Young Cricket in WarioWare Gold, Megumi Fushiguro in Jujutsu Kaisen, Jesse Cosay in the second season of Infinity Train, Goro Akechi in Persona 5, Hubert von Vestra in Fire Emblem: Three Houses and Fire Emblem Warriors: Three Hopes, Lloyd Bannings in Trails series, Prompto Argentum in Final Fantasy XV, River Ward in Cyberpunk 2077, and on-camera as Dorian Storm in the Dungeons & Dragons actual play web series Critical Role and its spinoff Exandria Unlimited.

[3] In 2007, Daymond moved to Los Angeles, where he worked as a college instructor at the New York Film Academy and Quixote Studio.

[5] In anime and video games, Daymond's roles have included: Tuxedo Mask in the Viz Media re-dub of Sailor Moon, Megumi Fushiguro in Jujustu Kaisen, Mumen Rider in One-Punch Man, Hubert von Vestra in Fire Emblem: Three Houses, Mike, Orbulon and Young Cricket in WarioWare Gold, Sorey in Tales of Zestiria, Goro Akechi in Persona 5, Lloyd Bannings in The Legend of Heroes: Trails of Cold Steel II and IV, Joe Kido in Digimon Adventure tri.

In 2023, he voices the main character, Chai, in the recently released rhythm action game Hi-Fi Rush created by Tango Gameworks.

[13][14] Polygon opined that Dorian had a "beautiful storyline" with Daymond's "stand out" performance which "was so integral to the start of Campaign 3" – "he participated in the cast's goofy asides and reactions, but also left room for moments of gravitas and emotional exploration.

[15] In 2023, he starred in the actual play Candela Obscura: The Circle of the Vassal & the Veil as Professor Howard Margrove; this horror anthology series was produced by Critical Role Productions.