John Fleckenstein—Fleck to his friends and colleagues—ascended to the role of Chief Operating Officer at RCA Records after a sterling run as co-president of the label. As the brother of industry legend Chuck Fleckenstein, currently a professor of Music Business at NYU, Fleckenstein, a native of Detroit, had an insider’s point of view into the industry that set him on his path. He built his career with internships at Columbia Records and Ruffhouse Records, which led to an assistant’s gig in the international department at Arista.

“I got great advice from my brother,” Fleckenstein acknowledges. “But I worked my way up from the bottom. And working my way up taught me the business inside and out. It is hard not to notice that my 20-plus-year path began and continues to this day in the Sony system. That should say a lot about this place as well. Look no further than Rob Stringer—this is the same system he came up in and now he passionately drives that forward today.”

Fleckenstein has also put in time at Jive, as well as relocating to Sydney to oversee marketing and promotion for BMG’s Asia-Pacific Region. These positions ultimately led to a job running Sony Music’s international team, where he cultivated a vast knowledge of global music strategy as he created worldwide campaigns for some of the world’s biggest stars, such as Beyoncé, Daft Punk, Justin Timberlake and Miley Cyrus.

Since joining Peter Edge’s RCA team in 2015, he’s played a pivotal role in the careers of breakthroughs acts including Khalid, Doja Cat, SZA and, most recently, Steve Lacy; and he’s rightfully proud of the key role he plays in the functioning of Nipper’s sophisticated, efficient operation.

“This might sound corny, but it’s all about the team,” Fleckenstein offers. “Artists sign with people, not labels—that’s the reality. We’re only as good as our people and how we move together. I spend as much of my time quarterbacking our team as I do trying to deliver world-class campaigns for our current family of artists and chasing the next great breakthrough.”

What would you consider to be the pivotal break in your career?
It was working on Santana’s Supernatural album. My first official job was at Arista as an assistant on the international team. I didn’t even know what that was; I just knew that everybody around me told me that you need to get your foot in the door, and you need to prove your worth and show people that you’re competent.

I was quickly faced with the reality of the music business—that things change a lot. I found myself in a situation where my boss had recently exited the company and we were without a department head for a few months. Clive Davis had signed Carlos Santana, and they agreed to work on a project together. Our team was short-staffed, and they basically came to me and said, “You’re doing a good job. Why don’t you look after this?” I was so excited to have my own project and to be able to stay on it even when my new boss came in.

The record was a hit in America, and it had all these Grammy nominations. We knew we needed Carlos to promote his album in Europe, as he had not been there yet. We planned a press conference for the day after the Grammys in Madrid. I was very excited, because I was able to organize this whole thing, and it was my first big trip.

It was initially meant to be a 24-hour trip for me. But following the Grammy Awards, the excitement over Santana exploded and the tour that he was about to embark on became mayhem with the media attention. Carlos and his team said, “We need you to stay with us and manage this whole thing,” and 24 hours turned into almost a month. That was the moment that I look back on now and realize how much it taught me. It was an incredible experience that gave me a perspective that I don’t think I could’ve gotten in any other way.

To watch that record explode the way that it did was extraordinary.

It was totally overwhelming. I saw first-hand how it affected Carlos too. It was such an amazing moment in his life, but I could also see the pressures he experienced as an artist. His experience has always stuck with me.

Carlos has said that his spirituality informs how he works. Has working with that kind of artist informed how you proceeded with other artists and projects?
Yes. Carlos is the real deal. He is not doing this because he’s looking for a check; he’s doing this because he has a vision and a purpose, and he has something that he must relate. I think about that even today in terms of how we find focus at RCA around true artistry. We want our artists to feel safe to create and experiment. We firmly believe that if you allow it and you surround yourself with the right people, you can be commercially successful and true to your message as an artist.

Read the complete interview here.