How Sierra Lever’s 'Plan B' Led To Her Becoming Head Of Hip Hop And R&B At Amazon Music

“I started to create opportunities in the city of Portland. I would book out nightclubs and throw parties.” She explained, “I would book 21-and-up clubs and ask for a Thursday night out of the week because it was too expensive to book a Friday or Saturday. They made an exception on Thursday nights to do 17-and-up events. I would throw parties but in between have three to four acts from my hometown perform during the 11:00 p.m. to 1 a.m. time period in between the DJ set.”

With the support of her mother, she solidified her confidence in bringing Portland’s music scene to her peers at such a young age. She would "wait in the car until the meeting [with the club manager] was over.”

After high school, Sierra attended college to cement her knowledge, leaning into her experience as a student-athlete. “I didn’t know this would be my career. I was going to school at Oregon State University studying media and communications really trying to figure it out. I studied TV production and I was working in sports." She added, "Music was my plan B. It was something that I wasn't sure how to get [into] being from a small town and a small city, but I knew sports. My plan A was to work in sports—whether that was working for a team or live venues like Crypto.com or Madison Square Garden—do marketing, and eventually become a general manager."

"Music was my plan B. It was something that I wasn't sure how to get [into] being from a small town and a small city, but I knew sports. My plan A was to work in sports—whether that was working for a team or live venues like Crypto.com or Madison Square Garden—do marketing, and eventually become a general manager."

"I thought I would go into sports because I knew it, I was an athlete growing up. I was more connected in that space," she continued. "I was into music, but I couldn’t work with [artists] in an extended way because I was so far away. Most artists were in Atlanta, New York, and Los Angeles. This was before the ability to really connect on social media. I was still in the community, but I didn't know where my place was. I was balancing both.”

While pursuing television production and working in sports, Sierra spent a great deal of her time on campus still pursuing her musical endeavors. “I was doing a lot at the time on campus doing shows, being the festival organizer at Oregon State, and linking up with friends that did concerts outside of the school. Some of the artists I worked with then were Big K.R.I.T., Too Short, Rapsody, 9th Wonder, and then I brought the first hip-hop artist to Oregon State's campus,” Sierra added.

Managing a heavy load, she was still able to break barriers at her alma mater by booking Macklemore and Ryan Lewis as the first headlining hip-hop act in the university's history during their meteoric rise of “Thrift Shop."

“They never had hip-hop on their campus prior. It was important for me in that position to say that I see the value. I see how important hip-hop is. I know students, I’m one of these students, and it would be a miss for us to not have hip-hop representation in our annual Oregon State Festival. I was able to convince the school to go ahead with an artist from the Pacific Northwest, he’s local, he's relatable, he’s hip-hop, and I was able to diversify the [line up] around that headlining act.”

As Sierra continued on to her master’s degree at Syracuse University, she was still leaning onto what she knew best, but this time, she finally took a chance on what she desired most. “I was doing this, not knowing exactly what a role in music could look like. I was finding out that I enjoy the marketing, but I also like radio promotion to call stations to see how much ads cost. I started to see all these different aspects in music, and I was meeting managers and artists and seeing how fans were connecting.”

“I was doing this, not knowing exactly what a role in music could look like. I was finding out that I enjoy the marketing, but I also like radio promotion to call stations to see how much ads cost. I started to see all these different aspects in music, and I was meeting managers and artists and seeing how fans were connecting.”

While Sierra was studying sports and event management, she continued to learn multiple aspects of the music industry. “I was still working on campus doing music events, building stages for the festivals, literally building with the team from the ground up. I was doing both simultaneously, and at a point, I decided this is my opportunity to take a chance. I was at Syracuse studying sports, but I was telling people I wanted to work for the Recording Academy and that I wanted to work in music,” she recalled.

After not getting an internship while at Oregon State, Sierra got creative and decided to reach out to a member of The Recording Academy directly. “There was a second chance, [I] saw another opportunity, and instead of applying for all of the chapters, I applied to LA because that's where I wanted to move, and I'd be at the headquarters. I was doing my plan A, which was sports, but behind the scenes [I was] trying to figure out where I could fit in and get into music, which was my plan B.” She continued, “I applied to the LA chapter and reached out to the director. I found her on Tumblr.”

Taking her shot, Sierra figured, either she still works at The Recording Academy or she’d get a bounce back if she’s no longer there anymore. “Or maybe she works in a different department and can lead me the right way, but I’m going to try regardless.”

Sierra sent in her application and narrative essay not realizing it was GRAMMY week. To her surprise, the director responded, and after an interview via Skype, Sierra was on a flight heading to Los Angeles to officially begin her career in the music industry. “That was my first entry into music, and it finally felt like I figured it out. I landed my internship, moved to LA and that's when music started to flourish and take off from there.”

After a decade of experience, Sierra has held positions at Sony Music, Universal Music Group, The Los Angeles Philharmonic (LA PHIL) Symphony Orchestra, along with various roles at The Recording Academy.

Sierra’s perseverance has led her to the career she’s always wanted, leading a team and inspiring others who are just as passionate about their love of music. “It’s important to understand as much as you can when working with others because you have to know what you do impacts how other people are able to work and be successful in their jobs.”

"The more you know, the better you're going to be as a leader and as a teammate. I've been able to take every step, from an assistant role to a coordinator role to a manager [role] to a director, to now being able to lead a team. It's very important to be aware of what others are doing and how your work impacts their work."

“The more you know, the better you're going to be as a leader and as a teammate. I’ve been able to take every step from an assistant role to a coordinator role to a manager to a director to now being able to lead a team. It's very important to be aware of what others are doing and how your work impacts their work.”

Now, as the head of the hip hop and R&B division at Amazon Music, Sierra continues to set the bar high and break barriers when connecting artists and fans.

Recently, Amazon music had hip-hop fans on the edge of their seats as Kendrick Lamar and other heavy-hitting LA artists presented a concert on Juneteenth live-streamed from Inglewood, California. She shared, “When we are bringing these live streams to the world, we want people to feel like they are there. The quality of our production was A1 and to be able to share those moments is just super powerful. The Ken and Friends livestream broke Amazon Music streaming records and earned the most minutes watched of any Amazon Music production. Those are the cultural moments we want to allow others around the world to experience. The livestream was able to bring it from LA to the world.”

"The Ken and Friends livestream broke Amazon Music streaming records and earned the most minutes watched of any Amazon Music production. Those are the cultural moments we want to allow others around the world to experience. The livestream was able to bring it from LA to the world."

Spearheading Amazon’s June campaign of Black Music Month, the Juneteenth livestream was a part of an initiative honoring the contributions of Black artists, composers, and songwriters who have defined culture. “Our campaign messaging was forever the influence. When Kendrick’s team and Free Lunch agency came to us about the event and wanting to work with Amazon Music to livestream it, we were excited. We’re really proud of what we were able to do together, providing the livestream and supporting the presentation of artists that were on that stage.”

From booking shows at Portland nightclubs as a teen to leading at Amazon Music, Sierra’s mission remains the same. “Wherever hip hop and R&B fans want to be, that’s where we want to be, too—support artists and amplify music to connect with people,” she concludes.

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