She began long affiliation with the Walt Disney Company in 1995. In 2001, she met Deke Sharon and founded the a cappella group Groove 66 at Disney's California Adventure theme park. She also began directing, arranging, and co-producing the group in 2004 under the name Vybration.
Since 2004, Dickinson has been the Principal Vocalist and Vocal Contractor for Pageant of the Masters in Laguna Beach, California. This job led to her meeting Danny Jacob, a Guitarist, Composer, and Producer. They collaborated on The Emperor's New School and on demos for the TV series Phineas and Ferb. Dickinson was a voice actor and vocalist for the series from 2007–2015.
In 2007, she joined the music group Spiritualized on their Acoustic Mainlines tour, which ended at the Coachella Valley Music and Arts Festival. She sang background vocals on their album, Sweet Heart Sweet Light (2012), and toured with them throughout North America in May 2012. Their Huh? tour included an appearance on Late Night with David Letterman and concluded with headlining the Sasquatch! Music Festival. She has been the opening act for Lyle Lovett and Tony Bennett. In 2016, Dickinson began working with Alan Chang as Michael Bublé's vocal contractor. She directed the choir on his album Nobody but Me and is the featured vocalist on the first song, "I Believe In You."