Lenny “S” Santiago is a man that trusts his instincts. “It was like 1995 and I was working at Bad Boy doing street promotion when I first saw Jay-Z’s ‘In My Lifetime’ video,” recalls the Bronx native. “That’s when I knew I wanted to work with Roc-A-Fella. I knew Jay was going to be big.”

It would take a few years before Lenny would see his premonitions come to pass, but there was never any doubt that he would work one Brooklyn’s finest MCs. His industry career began in the early 90’s doing street promotions for Bad Boy Records and its roster of fresh new talent. After a couple years of putting up posters, handing out fliers and getting vinyl to DJs, Lenny learned all the aspects of promoting an artist from the ground up. During the course of his travels, Lenny kept crossing paths with Roc-A-Fella’s head honchos.

“Jay and Dame would always see me promoting at the club and I would tell them I wanted to help them promote Roc-A-Fella,” say Lenny. “But they would look at me like, ‘Yeah, right. You Bad Boy for life.’”

But life has a funny way of throwing curve balls. Despite working with Bad Boy during the height of their success, Lenny was intrigued by the opportunity to spark an even brighter future with Roc-A-Fella. So he took a chance and interviewed with Jay-Z, Dame Dash and Kareem “Biggs” Burke to land a spot at the Roc. “My man at Penalty Records at the time told me that they needed someone to do street promotions,” says Lenny. “So I said let me get onboard to show them I’m serious.”

This time they believed him. So Lenny was hired to help out with street promotions. But in no time he worked his way up to head of department. From there he became marketing director, and eventually head of A&R. Lenny’s ability to multi-task furthered his knowledge of the music business and made him a valuable member of the Roc family. “I did everything. I took pictures, worked in the studio, coordinated shows on tour, produced and even DJed,” he says. “One time Jay’s DJ didn’t show up for a performance and Jay was like, ‘You need to DJ ’cause you know what to play.’ So I improvised and did some of his shows on the Hard Knock Life tour.”

But after playing a major role in the careers of artists like Jay-Z, Beanie Sigel and Memphis Bleek, Lenny decided it was time to take the next step. That led to a position as senior director of Urban A&R at Virgin Records. While most people fear change, Lenny was more than up to the challenge of bringing his experience and wealth of knowledge to a different home. “It’s definitely was a different environment at Virgin,” says Lenny. “It’s was a more corporate structure and there were more guidelines as to how things are supposed to be done, as opposed to Roc-A-Fella where I made my way learning as I went.” Now back at Roc-A-Fella (the house that Hov built) as Vice President of A&R, Lenny is back home working with Jay-Z, Memphis Bleek, Kanye West and a list of new talent that help make up the Carter Administration at Roc-A-Fella.

With much of the success behind one of rap’s biggest record labels and some of rap’s biggest names credited to Lenny S, there’s no doubt he’ll make the adjustment with no problem. It’s all about trusting your instincts.

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LAST MONTH'S FEATURE: Chris Atlas