Naiff was invited to participate on The Waterboys' album A Rock in the Weary Land after the group's leader Mike Scott heard his piano work in a studio next to one where the recording sessions for A Rock in the Weary Land were taking place. Naiff joined the band officially in June 2000.[2] Along with Mike Scott and Steve Wickham, Naiff made up the core of the post-2000 Waterboys band.[3]
Former Waterboy Ian McNabb described Naiff as Scott's "find of the century".[4] Not coincidentally, while keeping his membership in the Waterboys, Naiff also joined McNabb's touring band in 2004, and became a member of a revived version of McNabb's old band The Icicle Works in 2006.