Rejy Drayton joined We Are Rosie in early 2022. Not long after, he accepted his first role as a Rosie, becoming a Campaign Manager with The Trevor Project, the world’s largest suicide prevention and crisis intervention organization for LGBTQ youth.
Here, Rejy talks about going independent, becoming a Rosie, and the advice he has for all the flex-curious marketers out there.
Why did you become a Rosie?
I’ve been working in social media management for a while. I was getting a little frustrated and wanted to get out of the office and more into a free-form kind of career path. I stumbled upon We Are Rosie, which checked all of my boxes. It was really quick and really easy to make a profile, and then I wanna say three months later—just out of the blue—I got an email from Hope that told me about Trevor and it sounded perfect.
Why was your role with The Trevor Project a perfect match?
I had been following The Trevor Project since I was, like, 14, so it was a match made in heaven. I immediately jumped at the chance. I’m a queer person, so I knew of The Trevor Project from watching “Glee” and YouTube videos. I was just so ecstatic to have the chance to be working with an organization that was so integral to my formative years. It was very, very big then for me finding myself, and in me coming out. You know, any mention of Trevor, I’m there. It was really serendipitous.
How has being a Rosie impacted your career?
I graduated college two years ago and never in my wildest dreams would I think that I’d be working with an organization [The Trevor Project] that I’m so personally invested in and has such a history with me and my personal life. But also, just professionally—I mean, I’m working with some of the top brands in the world right now, and for me as a marketing professional, there’s a sense of pride. There’s a sense of satisfaction. It really helped me beat a lot of my insecurities and imposter syndrome, you know, just to be put in that position.
A lot of folks my age, they either had to have an internship to work with these companies or know somebody that was in there, that knew you in college or in high school, or you’ve racked up years of experience. I’m 25 and I know that a lot of my friends are just now getting into the career space that they wanna be in. So that’s why I think an organization like Rosie is immensely helpful to someone’s professional development.
What do you love most about being a Rosie?
The flexibility to travel. Oh my goodness—the fact that I don’t have to be in an office. I literally worked my second week with Trevor in LA—I’m based in New York—and I got all my work done and I was still able to do that.
The second thing that I would say is the culture at Trevor. I feel so supported. They’ve got these really awesome communities that you can be a part of. For someone that is so intersectional in my identity, that means so much that I can join the Bi+ group and talk with people that share my experience. I can join the Black group and talk with people that share my experience. So the culture at Trevor, and the fact that they prioritize mental health.
What advice do you have for other flex-curious marketers?
Going out on a limb like that is really, really scary. And I also understand your frustrations with the nine-to-five. I think the best in between would be We Are Rosie, where if you want that nine-to-five, they can find it for you. But if you want the freedom and flexibility of freelance while keeping the safety and security that comes with having a nine-to-five job, We Are Rosie is probably your best bet.
And I’ve been telling all my friends about y’all. I’ve been telling my roommates. Cause I thought all I wanted in the world was to work in an office, and then I did it and I was like, “This ain’t it. But if I leave, I won’t have anything.” I know what that feels like. I’m so lucky that I found Rosie and I would recommend it to anybody that’s dealing with that.
Interview has been edited and condensed for length and clarity.