When Warner Records appointed Steve Carless as A&R president, label CEO Aaron Bay-Schuck announced, “Steve-O has one of the most brilliant A&R minds in our business—driven by an innate ability to identify and nurture emerging artists and champion superstars.” From his start as an office assistant at Pharrell’s Star Trak Entertainment in 2003, the New Jersey native assumed a plethora of record industry positions, including Def Jam’s senior VP of A&R; president of Jeezy’s CTE World Recordings; business partner and co-manager of the late Nipsey Hussle and co-founder of the Marathon Agency; and A&R executive of Beyoncé’s Black Is King visual album and The Lion King: The Gift soundtrack complement, among other roles. Carless is a six-time Grammy winner.

What was it like trying to get into the business?
When I was trying to get a deal, I didn’t have access to people; I couldn’t DM somebody. We would get in our cars and chase people down! I bought every magazine I could: The Source, XXL, you name it. Whenever I saw someone from the industry’s name, I wrote it down, made notes about what they did. It was like a Rolodex with no phone numbers. But when I finally met folks like Steve Stoute, I knew their history.

Do artists need to arrive with their own followings in order to be signed nowadays, or are you willing to build that with them when they arrive at the label?
I have this conversation all the time. Some of us are from the era when signing things with our gut was worth it. Don’t get it twisted: Those things still happen today, more often than people see or believe. But there have been generational shifts in technology and social media. Technology has afforded so many opportunities. One side of me feels you should get your shit together first and then come holla at me. But there’s still the other side of it—as a person who loves the music, whatever piques my interest is what I go after. I don’t have a fixed point of view on it. They should have some kind of activity. Groups should be able to cultivate some kind of audience, because a lot of this is pooled from who likes you. Everything else that I can do is help scale it, not create or manufacture it.

What drove your decision to go to Warner Records?
The DNA of the company and supporting entrepreneurs. I felt like there was an incredible opportunity of timing, because they were just transitioning to a new space and momentum that I felt like I could contribute my expertise to. What we understood together is that they were missing an undertone of “new generation” from local and regional scenes that would cover a part of the genre that a lot of the other record companies had overlooked, and they were gonna allow me to innovate a point of view.

What have you discovered about the Warner culture?
It’s a culture that’s predicated on humanity. It’s a different textural warmth. Warner has a quaint, intimate atmosphere, despite what it is in its magnitude of size. But I really feel the warmth of the people and the passion for where we are going. I love the way that everybody is focused and hungry. I’m also getting the experience of what it’s like to have two chairmen who come from different places in the record business leading this company with such a major legacy. I’m so happy to get that experience, because I’m learning from both of them.

How is it specifically working with Aaron Bay-Schuck and Tom Corson?
They both have such business acumen and creative foresight. I think Aaron’s an incredible visionary. It’s always great to talk to an A&R man, because I’m an A&R man. There are just certain nuances about the job that become challenging to articulate depending on who you are and where you’re at and what the company’s doing with an artist. Number one, he’s artist-first; he’s about the people. And then he’s about how we can contribute to the betterment of society.

Tom is great because he just has this immaculate leadership and a depth of experience that gives you a mentor-base kind of thing that I find a deep value in. Because he’s run the marketing department, he understands operations. He’s led so many companies to their successes, it’s like having that dichotomous understanding that helps him be a more well-rounded executive.

And Karen Kwak?
Karen Kwak is my partner, my road dog. I came up in Karen’s department working at Def Jam, so it’s a full-circle moment for me to be back in the coop with her. I always thought of her as one of the most brilliant operational executives I’ve ever been next to. Because she just took chances on certain kinds of executives that I’ve never seen any A&R executive take chances on. She’s stewarded in all kinds of folks: DJ Khaled, No I.D. Her body of work and just believing in those types of personalities. We made it all about making records and being pure with the artist’s dream. She and I get to be hand in hand and steward this new direction at Warner.

Read the complete interview here.