10 Questions With Lilly

There are few things we love more than welcoming a new teammate—and this week, we’re thrilled to introduce Lilly O’Leary to the Cutline Crew! Lilly’s creativity and passion for storytelling run deep (just wait until you read about her parents’ backyard!) and her recent work has us feeling starstruck. Curious about which iconic performer she partnered up with? Scroll on for all the details and to learn a few fun facts about Lilly.

The obvious question: Why PR?

I love being able to give people a platform to tell their stories in a strategic and impactful way. We all have a story to tell and more often than not, we’re served a monoculture of the same people, stories, and platforms. 

I take pride in finding diverse stories to tell—be it about people or brands that serve the greater good. Now more than ever, we need to connect and uplift each other, especially communities that are underrepresented or often go unheard. It's my job to ensure inclusive storytelling is at the forefront of my approach to media strategy every time. 

What's been your greatest moment on the job so far?

Running a two-day media event with Dolly Parton! At my previous agency, we were given the opportunity of a lifetime: to launch a line of baking products with The Queen of Country herself.

Over the course of two days, we managed more than 30 interviews, which were live, editorial, and pre-taped. While this was a beast of a launch, Dolly Parton made it easier. She is without a doubt the hardest working woman in the world. She is also graceful, generous, kind, and an absolute delight to work with. 98 percent of the interviewers cried during their segment, but seeing the impact that this woman has had on so many was incredibly memorable. 

I was also able to book my first live Today Show appearance during this time! But let’s be honest…. when Dolly is the talent, your life is a lot easier. 

Who has influenced you most when it comes to how you approach your work?

I’m continuously in awe at the women of PBS Newshour. I grew up watching the Newshour with Jim Lehrer, and since his passing, Judy Woodruff, Amna Nawaz, Lisa Desjardins, and Yamiche Alcindor have taken center stage. These women are truly examples of what it means to be a woman in media. 

From being mansplained on live TV to having to stay calm and balanced in the face of adversity, I’m always inspired by their approach to storytelling. They’re intentional about their stories and guests, and work extra hard to highlight those who are often overlooked for commentary—and they always showcase a human element in their segments. I look at this approach to journalism to inform my own strategic storytelling. 

Do you have a hidden talent or secret hobby? What is it?

I've had a passion for interiors for as long as I can remember! Be it design or decor, I would spend the better part of an afternoon as a kid reimagining my bedroom. One year, when I was newly print mag obsessed, I transformed my bedroom into the inside of a Vogue Magazine. Each wall had its own editorial section.

While some people dread moving, I like to see a new space as a blank canvas and recently, I’ve become pretty good at thrifting apartment decor in New York. About 80 percent of my furniture and decor have either been thrifted or stooped! 

Where is the most inspiring place you've visited? What made it special?

Here’s a curveball… my parents’ backyard! 

Both of my parents are teachers, and more specifically, teach within the world of theater. When the pandemic hit, they were both struggling to fulfill their creative desire to connect with their theater community. As a way to adapt (as we did), they created the Shake Shack (The Shakespeare Shack) where they hosted outdoor community reads so that they and their theater friends could come, act, sing, read a poem, or do something else to express themselves. 

Since then, my dad (who just retired this summer) created a full-blown theater in our backyard made entirely of driftwood and fallen trees. It’s a beautiful tribute to creating community in the face of adversity, which is something that is incredibly important to me. 

What’s something you saw recently that made you smile?

My own backyard. After four years of living in teeny tiny claustrophobic apartments in Brooklyn, I finally have a backyard. And I can confirm, a tree does grow in Brooklyn! Martha Stewart, move over. 

What advice would you give to your teenage self?

This is NOT your peak. 

If you could write a book about your life, what would the title be and why?

Help! I’m Over Functioning Again! 

I tend to be a very go, go, go person who, to confess, craves control. This plays out in many ways, but as my incredibly wise therapist once said, it’s important to recognize when you are over-functioning. For some reason (maybe denial?), this was the first time I heard this term. While now half joking and half very serious, it has become a bit of a mantra for me. 

For example, I love planning parties. Is claiming responsibility for signature cocktails, apps, vibes, and decor over-functioning? Yes! Do my friends understand that this is the way it has to be? Also yes. 

How do you like to start your day?

I love waking up with an iced coffee and the Las Culturistas podcast. Bowen Yang and Matt Rogers are the only people allowed to speak to me before 8 am. 

What's your favorite quote? What impact has it had on you?

“What will survive of us is love.”

As cliche as it sounds, we’re living in an incredibly tumultuous time. Hearing this quote reminds me of how imperative it is to seek out love and give it back in return. Does this quote get lost on me when I am behind a slow walker? Absolutely.