Leopard Print, Internet Culture and Fresh Air: Inside Jennifer D’Angelo’s Freelance Groove

The creative director shares how leaning into internet culture and independent agility through We Are Rosie keeps her creative sharp

In modern advertising, social is the ultimate litmus test: you know instantly whether your joke landed or bombed. And that’s exactly where Jennifer D’Angelo thrives.

A versatile creative director and copywriter with stops at shops like Laundry Service, Edelman, and Monks, Jennifer excels at blending earned buzz with internet-native social storytelling. For her, modern greatness isn’t about big, serious manifestos; it’s about hyper-relevant casting, a strong sense of humor, and creating copy that sounds human.

Today, the freedom of the We Are Rosie network allows her to say yes to unexpected challenges, try out emerging tech, and live near family in the Rockies — all while creating work that racks up comments in the wild.

We chatted with Jennifer about the domino effect of honesty in brainstorming, finding magic under stress and turning wild pitch ideas into viral wins.

The following has been lightly edited.

What’s a creative hill you’ll die on?

Show up unabashedly as yourself, and everything else will flow; the ideas, connections with teammates, and so on. When you lead with authenticity, suddenly others feel free to share what really inspires them, makes them laugh or grinds their gears. It’s a domino effect that I’ve found always leads to more honest, unique creative.

Finish this sentence: When I am in a creative rut, I _____.

Go for a walk around my lovely neighborhood and soak up whatever brings me joy. Gelato, the cat cafe down the block, my favorite local boutique. Ideas spring from the most unexpected sources, especially when you fill your own cup with fresh air (and dark chocolate ice cream).

What is a newsletter, creator, or account everyone should follow?

I’ve been geeking out on Reformation’s content for years now. They’re one of the few brands whose emails I actually open on a regular basis and digest fully (shout out to their genius copywriters). I find myself turning to their socials over and over again for inspiration on everything from vibes (they’ve nailed the cool girl aesthetic/voice) to branded partnerships. Making Monica Lewinsky the face of their workwear line? Iconic. Turning Pete Davidson into the brand’s official boyfriend? Slow clap.

What’s a project topic, industry, or creative challenge that always gets you excited to jump in?

I’m always stoked to work on social, which is probably why it’s 90% of my book. Seeing your ideas in the wild on such a regular basis is a trip! It feels a lot like stand-up — you’ll know instantly whether you’ve hit the mark or not. And there’s truly nothing more satisfying than watching the internet respond positively in the comments; it’s genuinely the highest compliment.

What’s an emerging tool or technology that has elevated your work, and how?

Gemini. As a freelancer, I spend a lot of time hopping between different accounts that I may or may not be all that familiar with. AI has helped me expedite my understanding of the products, verticals and audiences on any given project. It also helps me use lingo without sounding completely clueless and out of touch.

How has your definition of “great work” changed over time?

Early on, I wanted everything to be BIG. An award-winning concept, a never-been-done-before execution. But nowadays, I get a thrill over the small details: unexpected casting, art direction filled with deep cuts, copy that sounds human. I think it comes down to creating work that is genuine and really, truly gets its audience in a way that’s almost intangible.

What’s a strength you bring to a project that doesn’t show up on your resume?

My sense of humor and down-to-earth nature go a long way on stressful accounts. Timelines and clients can be demanding enough. Sometimes just keeping it real with your teammates, acknowledging the stress, and laughing through it can bring a certain magic out in the work. When everyone is anxious, it comes through in the creative and brings the finished product down.

Tell us about a recent We Are Rosie project you’re proud of?

Last year, I helped launch a new fried pickle product for a chain restaurant. On a whim, I threw an idea out that involved a somewhat polarizing reality star who was near and dear to my Jersey heart (and who I happened to know was obsessed with pickles). It was a shot in the dark, the kind of partnership I didn’t think I would get to work on. But next thing I knew, I was digging into the 2010 archives, writing scripts filled with IYKYK references, and leading a shoot that felt like a hilarious, leopard print-fueled fever dream. The content wound up blowing up on social and surpassing all KPIs. The entire experience was surreal; it lives rent-free in my head.

What are the unexpected advantages of freelance work?

There’s a certain freedom in being the freelance unicorn who gets to hop in and out of projects. Because of the temporary nature of the work, I’ve found myself saying yes to opportunities I might have never considered before. I’ve let go of so many of the concerns I had as a full-time employee: that an account might not be up my alley or I might not be experienced enough to take on a certain task. I find myself jumping in for the sake of learning something new and seeing where it takes me.

What’s a bucket-list win you’ve been able to check off with the support and flexibility of We Are Rosie?

Since Rosie allows me to work remotely on all projects, I decided to lean all the way in and move to a new city: Denver. I’m now just five minutes down the road from my sister (my first time in a decade living so close to family, which has been lovely). It’s been a literal breath of fresh air getting to experience everything Denver has to offer: a highly underrated music scene, fantastic boutiques and dive bars, gorgeous mountains, and some of the most friendly people I’ve ever met. Also, shockingly good sushi for a land-locked state.

You’ve got 2 minutes with the industry… What’s your hot take?

This is going to sound very 2022, but let’s just own the fact that teams don’t need to go into the office to do great work. Also, everyone in the industry should get an AMC Stubs pass. It’s genuinely the easiest (and most cost-efficient) way to stay plugged into culture. While we’re on the topic, if AMC ever needs a Creative Director…

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This 2 Mins With is part of an ongoing series in partnership with We Are Rosie, a platform connecting brands with top-tier independent marketing talent.

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