I was looking for an assistant, and, true story, someone who worked for me mentioned that her dentist knew a great girl who was looking for a job. So, how do you not trust a dentist? He introduced me to his patient, Jessie Gloger.
This was during the pandemic. At first, I met Jessie over Zoom, then we spoke on the phone. But honestly, I wasn’t sure I needed an assistant at the time—I was in lockdown in Sag Harbor, and Jones Road was still just a concept. We stayed in touch, and one day Jessie called me and said, “I want to be your assistant. I’m in Sag Harbor and ready to work.” It turns out her boyfriend's family had a house in the neighborhood, and she was staying there.
So, Jessie came to my backyard wearing a mask, and I started giving her small tasks. As she handled each one, I gave her more to do, eventually bigger responsibilities. She just showed up, figured things out, and got things done. It was a time when there were no rules, not much going on, and I was in the early stages of launching this new brand. Jessie turned out to be incredibly resourceful and capable.
Her story is a reminder to anyone starting a new job: be the person who’s invaluable and isn’t afraid to take on anything.
Hi everyone! I’m Jessie, a previous assistant of Bobbi’s. I’m excited to share my career journey and the lessons I’ve learned along the way.
I always knew I wanted to be part of the fashion and beauty world. I loved everything about it, and it felt like a motivating place for me to build a career. It wasn’t always a straight line, but every step made sense in its way and helped me develop important skills along the way. Here’s how it all came together.
In college, I jumped at every career opportunity I could find—ambassador programs for apps being marketed on campus, summer internships, and working part-time for a local jewelry brand. Most career lessons aren’t found in textbooks—you have to create real-world opportunities for yourself. Leverage LinkedIn, university job boards, and professor connections, and never underestimate the power of a cold email. These early experiences will set you apart and build a diverse toolkit that you’ll carry throughout your career.
When I graduated, I knew I wanted to be in New York City, even though I didn’t have a job lined up or connections in the city. I found a PR training program with a healthcare company—not exactly my dream industry, but I chose to view it as a stepping stone. It taught me that sometimes, the industry might not be the perfect fit, but the skills you gain can always be transferable. You have to be open to learning in unexpected places.
As the PR program was wrapping up, I started putting my new publicity skills to work by networking with anyone and everyone. Through a networking connection, I learned about a “confidential project” Bobbi Brown was working on where she needed an Executive Assistant. It felt like fate. I didn’t have the exact assistant experience needed, but I trusted that my communication and organizational skills would pair perfectly with my enthusiasm and determination for the role. And for reasons I’m still so grateful for, Bobbi took a chance on me. That’s when I learned that sometimes all it takes is being bright-eyed and confident to open doors you never thought possible.
Bobbi gave me essential advice on my first day: Be a sponge. Absorb everything. And I did. I tackled every task, from walking her dogs to taking notes at meetings with industry legends, with that mindset. Through consistent work and trust, I became more than Bobbi’s assistant; I supported her personal PR efforts along with brand marketing for Jones Road. Bobbi became not just a boss but a mentor, and I leaned on her to help me identify my strengths—storytelling, creativity, and relationship-building.Since then, I’ve continued forging my career around what I love. I moved on to CUUP, where I was one of two brand marketers for the women’s intimates startup, further honing my skills. Now, I’m part of the Brand Creative team at Madewell, where I get to merge creativity with brand vision. At each step, I’ve kept my mentors close, stayed curious, and embraced the power of learning by doing. What’s been key for me is realizing that this journey has always been about more than just a career—it’s about growth, resilience, and finding purpose.
Life, like a career, is full of unexpected twists and turns. You don’t need to have everything figured out to move forward. Trust yourself, trust the process, and keep showing up. Every experience is valuable, and every challenge you overcome shapes you into someone more capable and confident.
So here I am, still on this journey, excited for what’s next and always ready to say yes to the opportunities that come my way. And that’s my biggest takeaway—keep going, stay open, and never stop being a sponge.
Always rooting for you,
x Jessie