Discovered by DJ Clark Kent,ki was originally known as "MC Will-Ski". In the 1990s, he was a member of the group Original Flavor, the first group managed by future recording industry executive Damon Dash.In the mid-90s, Ski was working on duo Camp Lo's debut album Uptown Saturday Night when Dash called him in to work on the debut album of his own artist, Jay-Z. Jay's album, Reasonable Doubt, was released in 1996, marking Ski's first major production placement. Ski produced four tracks off the album, including the singles "Dead Presidents" and "Feelin' It".

After the critical success of Reasonable Doubt, Ski formed Roc-A-Blok Productions in affiliation with Jay and Dame's label, Roc-A-Fella Records, working with Camp Lo and Sporty Thievz. The producer crafted most of Camp Lo's debut, which dropped in 1997, and produced the Fat Joe single "John Blaze"; Ski continued to work with Jay-Z, on his second album In My Lifetime, Vol. 1 as well as non-solo albums and compilation projects, until 1998, when Jay released his third project Vol. 2... Hard Knock Life without beats from any of his former producers except for DJ Premier.

Though Roc-A-Blok Productions had since folded, Ski stayed somewhat active in music. Relocating to his home state of North Carolina for a break from New York City's fast-paced lifestyle, he continued producing for artists such as Nature, members of the New Jersey crew The Outsidaz, Lil' Kim, Foxy Brown, Ras Kass and Proof. The producer has continued to produce for Camp Lo, providing most of the production for their second album Let's Do it Again, as well as their third album, Black Hollywood.

Recently, Ski linked back up with Dame Dash, joining the entrepreneur's DD172 collective, subsequently nicknamed the 24-Hour Karate School. Since the foundation of the studio enclave, Ski has worked with Mos Def, Jay Electronica, Jean Grae and others; on April 30, 2010, he announced that he will be producing upcoming albums for Jean Grae, Joell Ortiz, Ras Kass and others, and will be producing all but three songs on the rapper Curren$y's 3rd album Pilot Talk ; these artists are also all featured on the producer's upcoming solo debut, entitled 24 Hour Karate School in honor of the collective.