So, You Work At Playboy?

Playboy
Naked
Published in
6 min readApr 9, 2020

A new job is usually an exciting piece of information to share, though in some instances broaching the topic may require more nuance than in others. Curious how our own employees experienced this, we asked Playboy staffers to tell us their stories of how they shared the news with friends and family.

Tori Adams, Associate Editor

On Telling Her Mother

My mom was super excited, but halfway through jumping for joy she paused — probably when it sunk in that it was Playboy. I had to explain I was writing and editing, much like the hustling I’d been doing for over a year at several magazines in internships and contract jobs, but this was finally a full-time, steady career. After understanding a little more about the brand, both my parents were really jazzed that I got the opportunity.

Jake Waxenberg, SVP, Corporate Development & Strategy

On Telling His Mother-In-Law

I told my mother-in-law that I’d left my job in venture and had joined Playboy. She was shocked and confused. As I always do when I explain this choice, I shared with her the ability Playboy has to be a driving force in culture, fun and expression and that the chance to do that with an iconic brand doesn’t happen very often. After I walked her though that, she lit up and was excited about what’s ahead.

Regina Rosato, Associate Art Director

On Telling Her Uncle Paulie

Having been a lifelong fan and subscriber of Playboy — for more than 30 years, in fact — my uncle Paul was ecstatic when I conveyed the news that I’d been hired as an art director at the magazine. As a bonus, I was delighted to hear he still has a stash of vintage Playboys in the basement of my grandparents’ house! He thought of throwing them away many times but now feels validated as he always knew there was a reason for keeping them. He was genuinely gratified to see them take on second lives as inspiration for me in my new position. Thanks, Uncle Paulie!

Diego Orozco, Accounts Payable Clerk

On Telling His Mother

One time I wore a Playboy sweater to a carne asada at my parents’ house, and my mom kept bringing out different hoodies from my dad’s closet for me to change into. Now I wear only Playboy merch when I visit her.

Joey Coombe, Senior Archivist

On Telling His Family

On my last visit home, my family shared stories about telling people what I did for a living. I was surprised how defensive they were about my job, how they took time to inform people that I did not hang out with Playmates all day or work at the Playboy Mansion, that they took the time to really listen to me when I talk about preservation and digitization. I love how proud my family is of the work I do, but more than that, I love the irony of how seriously they take a job that is so ripe for comedy.

Becca Pizzello, Lead, Product Manager

On Telling Her Parents

My dad worked for a printer for 38 years, so I decided to interview with them. I went through three rounds of interviews before I got a call offering me the gig. I told them I’d get right back to them and hung up. Not 10 minutes later I received another phone call. When I picked up I was surprised to hear a new voice on the other side of the line, a recruiter asking me if I would be interested in interviewing for a receptionist position at Playboy Enterprises. “Sorry, what!?” Is what I think I replied. I hung up, called my mom and dad, told them what had happened and asked for their advice, thinking my dad would be a bit torn about my not accepting the other offer right away. I was wrong! He immediately told me I would be an idiot for not going to Playboy. And of course my mom couldn’t let me forget all the times I’d binged Girls Next Door. Let’s just say the rest is history. It’s almost eight years later, and I’m still thanking the universe for not making me sell copy machines and instead giving me the opportunity to grow my career with this amazing Playboy family.

Adrienne Williams, Marketing Director

On Telling Her Father

“Soooooooo, I work at Playboy now” are the words I said over the phone to my father, a retired pastor from the Caribbean. The tension was palpable as I waited in silence for his response. After what seemed like hours, we both erupted into laughter, and I reassured him that my job would be like any other marketing job I’d ever had. Well…kind of.

Elias Escalante, Video Editor

On Telling His Mother, Silvia

When I told my mom, she was happy I’d found a job in what I’d studied and in something I liked. After I started I told only a few friends and family members about working at Playboy; I didn’t want to get any bad comments or negativity. Not a lot of people know what Playboy stands for today, and I’ve learned a lot working for the company. Now I share that knowledge with more people in my circle and have gotten good feedback on all my projects.

Cameron Thomas, SVP, Financial Planning and Analysis

On Telling His Friends

People always ask me if there are Playmates and Bunnies walking around the office. I don’t want to burst their bubble, so I say, “Yep, every day!”

Denise Walter, Senior Manager, Corporate IT

On Telling Friends and Family

People I never talk to, friends of friends who I know nothing about, will come up to me at any sort of get-together and start asking about Playboy. I find it funny, because it’s almost as if when you start working here it becomes the most interesting thing about you. Also, if I call a company for support, a lot of the representatives will say things like, “I’m curious, is this the real Playboy? What’s it like working there? How’s the Mansion?”

Anna Ondaatje, VP, Global Brand and Franchise Strategy

On Telling Her Grandfather

The day I accepted the job I called my grandfather to tell him I was going to work for Playboy. There was a pause on the line, and then he said, “You know, Playboy has always had really great…articles!

Alan Huynh, Director, Performance Marketing

On Telling His Parents

I told my parents while we were out at dinner. Knowing my mother would have some initial assumptions about what working at Playboy would mean, I broached the subject as “I’m leaving my job at an advertising agency to join a media publication.” After some back and forth, and some probing questions, I finally spilled the beans that the publication was Playboy. The facial expression on my mom was priceless. Later that night, though, my dad approached me and said that never in his wildest dreams when he was a teenager stealing glances and ogling photos of the magazine from afar did he think he’d be one connection away from Playboy — and most important, that his son, of all people, would be working for such an iconic brand. Unlike at dinner, which ended quickly after I’d relayed the news, my dad gave me a big long hug.

Emiliano Garcia, SVP, Corporate IT

On Telling His Friends and Family

The question I always get is if there are naked women walking around our offices. I always have to explain that it’s not what they think. It’s corporate, much like any modern corporation might be.

Holly Ruprecht, Associate Director, Subscriptions

On Telling Her Friends

A lot of my friends and family were excited to hear I would be working at Playboy. Coming from the adult industry, I actually had to let a lot of my friends know that if they came to the office for a meeting, they might want to dress more professionally and be quiet while walking around because it’s a place of work and not just a fun place to hang out.

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