Why Jessie Reyez Is At The Inflection Point Of Her Career

Danny Desatnik
Mar 25 · 9 min read


Jessie Reyez (Middle) with ItsTheReal. Jeff Rosenthal (Left) and Eric Rosenthal (Right)

What was your first introduction to the artists that make up your Spotify playlists? Well, my introduction to Jessie Reyez came from an interview with ItsTheReal. “Yo, it’s Jessie Reyez aka Pine-sized Colombian thug”. I was drawn to her confidence, thoughtfulness and ability to remain unapologetically authentic throughout all one hour and fifteen minutes of that interview. Her music gave me a similar feeling — The confidence and struggle of Toronto with a palpable Colombian flavour. I instantly became a fan that day.

Later that week an interview between Tom Powers (CBC Radio’s Q) and Jessie showed up on my Twitter feed. Remembering what I heard earlier, I wanted to listen to what she had to say. Less than five minutes into the interview Jessie delivers two simple, yet powerful gems.

“We have to make sure we build the foundation properly”

“I feel like the way people consume music right now is beautiful for discovery but difficult for respecting a whole project…”

Jessie gets it. She understands the landscape and how the business aspect is at heads with an individual’s artistic expression. After listening to the two interviews, it was evident that Jessie had a plan to build this foundation stronger than most. Curious to understand what this plan was, I decided to dive deeper by reading articles, watching interviews and listening to her music for hours on end. What I came to understand is that we are right at the inflection point of Jessie’s career, moving from constructing the foundation to household recognition.

The foundation is extremely valuable since we live in a world where virality is common, product cycles are short and longevity feels like a foreign concept. Analyzing the foundation is easier by breaking it down into two objectives:

  1. Build a fanbase that will listen to your album in its entirety
  2. Experience performing in all venue sizes

To give a better picture of what Jessie’s path has entailed so far, see the image below.

An overview of Jessie’s career so far

OBJECTIVE #1: Build a fanbase that will listen to and value a whole album

Before going any further, look at what Jessie had to say about her debut album during an interview with Nadeska on Beats 1.

“Attention spans are getting shorter by the year, right? There are only a few artists that can command that sort of respect to be like this is a project, and people will sit down and listen to the full-length project. To bring it back to what I was saying about earlier, time is the most expensive thing we have. For someone to do that, it’s because they trust you, they trust that you’re going to contribute something to their lives, something to the time they are sacrificing and there is going to be an exchange. So I feel like I poured everything into these last two EPs; I polished, I sacrificed, I cried, I lived and I’m really happy and fortunate that they have connected and I feel like I had to do that to make sure that I'm proving myself, that I know I deserve the respect, the exchange, that moment of attention, of a full length.”

After coming across that interview, it was evident that the first task is building an indestructible level of trust with fans through multiple exchanges of value. Why is that important? Well in Jessie’s case, she believes that having fans who listen to a full body of work is a key indicator of success. Building trust involves connecting with someone on an emotional level with a high level of frequency, which in the case of an artist can be achieved through music, live performance, and fan engagement tactics.

To start, check out Jessie’s Twitter bio:

As you can see, Jessie sings and writes songs about stuff that she doesn’t like to talk about. This immediately lets us know that she operates from a place of vulnerability. Topics range from sexual abuse to self worth to immigration. For example, songs such as Saint Nobody, Shutter Island and Far Away are made up of powerful messages that are wrapped into well produced songs. Many of these songs hit home for music listeners as they too have gone through similar situations. Beyond her own work, Jessie has strategically approached collaborating with artists who fit her overall vibe and sonic aesthetic. These collaborations can be seen as a way to experiment in a low risk environment while gaining exposure to new listeners at the same time. For example, teaming up with Eminem on Nice Guy exercised her brash rapping capability. In another way, teaming up with Juan Magan on Wherever You Go showcased her natural fit within the Latin genre.

Listening and analyzing an artist’s music is one thing but seeing them live in concert is integral to winning the trust of a fan. From my experience, some artists do a phenomenal job on stage bringing you into their world using lights, instrumentation and a high level of energy. Jessie belongs in that conversation. Her ability to engage with the crowd and let you experience the emotions expressed in each song, all the while beaming with personality, makes you leave her live show a true fan. From 2017–2020 she has gone on two headlining tours, supported multiple artists and played at some of the biggest festivals. To put it another way, that is 120+ opportunities she has created for music fans to connect with her.

If that wasn’t enough, Jessie and her team have made an effort to engage with fans through three mediums:

Gatekeep was released in May 2018

Emotionally driven content. The most powerful piece of content by far was her Gatekeepers documentary which cinematically recounts a life changing personal experience in the music industry. Content that is emotionally driven helps fans understand the artist’s experience, giving greater meaning to the related song.

SMS marketing. Visual content aside, she has made an effort to connect with fans through Community, a SMS marketing tool. Some fans value connecting with artists since it offers social currency such as displaying your conversation with the artist on social media. In Jessie’s case, using Community is more strategic. The messages delivered in each of her songs really resonate with fans who then, in turn, want to communicate to her how much she means to them. This digital exchange of acknowledgment delivers more value than most.

Jessie on Instagram live listening to fans play their own songs

Live Streams. Currently, the world is experiencing unprecedented times due to the CoronaVirus pandemic. Jessie is an example of someone who has looked past the paralyzing situation to connect with her fans and create more of a community around her artistry. Using Instagram live as a medium, Jessie has taught fans the chords to her songs while giving those same fans the opportunity to play their own songs for the virtual audience. If not for keeping herself sane, these sessions have grown into a time where fans can connect over the shared love of music. These sessions display how impactful her music is to her fans.

Jessie and her team have been very intentional with the music and content released to ensure that fans are emotionally connected. Fans look to Jessie for inspiration and wisdom as much as they value a picture with her. Building on the story told so far, I’m confident in saying that fans will be eager to listen to the album top to bottom.

As a side note: The analytical part of me is interested to know how many pre-saves she receives. Last year I read an article that articulated how a fan who pre-saves a song or album is four times as valuable than the average listener in that artist’s fanbase.

OBJECTIVE #2: Experience performing in all possible venue sizes

A label supports many artists with a limited amount of resources made up of financing and human capital. Artists who can rely on the output of their immediate team and continue to grow are very attractive investments to labels, who at that point have no choice but to throw fuel on the fire. One way of doing this is to craft an album deal where you are allowed to put out a project independently before the debut album. In the time before releasing your debut album, the opportunity to continue to grow and engage with your fan base can convince the label that your budget should be larger. Since we have talked about how Jessie grew her emotional connection with fans, let’s turn the focus to the live performance aspect.

Jessie performing at the 2017 BET awards

Think about the understudy of an actor or actress. Observing the processes, learning from the mistakes and getting a chance to practice are essential aspects to finally executing in the wanted role. Similarly, as an artist you want to be able to experience what your next step feels like before making it. Jessie hit the jackpot when signing with Zach Iser at CAA, who currently represents SZA, Future, Anderson .paak among many others. Under Iser’s leadership, Jessie has been positioned to open for artists that afford the ability to experience what the next step in the journey looks like. Over the past three years, three opening slots really stuck out to me:

PARTYNEXTDOOR’s ‘Infinity Tour’ (Europe leg) — February 2018

Jessie had just completed her first headlining club tour during the Summer of 2017. Opening for PND in Europe exposed her to theatre sized venues in a low risk environment. She got to experience theatre audiences before her headline theatre tour towards the end of 2018. In addition, the audience every night connected with alternative R&B music.

Halsey’s Hopeless ‘Fountain Kingdom Tour’ — July 2018

Jessie had finished opening for PND, giving her and her team the chance to enhance the live show. Five months later she opened up for Halsey, exposing her to even larger venues as it was an amphitheatre run. Additionally, both Halsey and Jessie exude empowerment and are known for their unapologetic nature in the pop/r&b realm. Touring with Halsey helped to incubate new fans in locations and venues Jessie had not toured before.

Billie Eilish’s ‘Where Do We Go Tour’ — March 2020

Opening up for Billie would give Jessie exposure to Arenas and stadiums. At this point, she would have played in every type of venue, giving her the ability to execute on the largest stages. Unfortunately, the global pandemic struck and postponed the tour with only two shows completed.

From the examples above, it’s evident that Jessie’s team has done a great job to give her the experience she needs.

Another part of touring I didn’t cover is festivals. Jessie has played at major festivals in 2018 (Bonnaroo, Lollapalooza) and 2019 (Osheaga, Fire Fly, Governors Ball) and was booked to play at Coachella in 2020 before it was postponed. If the experience wasn’t valuable enough, Jessie went out on her second headlining tour in 2018 which included 31 North American shows. Comparing the 13 shows in 2017 to the 31 shows in 2018, which were all at higher capacity venues, shows tremendous growth. Objective achieved. At this point, you have to assume that the label is getting ready to take this to the next level.


With an extremely strong team around her, an indestructible foundation and the support of a major label, it’s hard to believe that 2020 won’t be the year Jessie takes off. Before, the question was is she going to take it to the next level. Now, it’s about how. What will be the strategy and tactics used by her team? Collaborating with artists in the latin music world? Innovating her sound? Endorsement deals? If the past is any indicator of what is to come, we are in for one hell of a show.

Jessie’s debut album ‘Before Love Came to Kill Us’ comes out this Friday, March 27.

Danny Desatnik

Written by

Writing to 🏋🏼‍♂️my 🧠 Strategy. IP. Music Industry. Content Creation. Sports. all opinions are mine

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