Anna Ondaatje on How a Culture Shift Led Playboy to Shift Culture
Mixing Board Studio Session
Mixing Board Member Anna Ondaatje most recently was the Global Brand & Franchise VP of Strategy at Playboy where she helped lead a massive transformation of the brand over a three-year period that also saw the company go public. Before Playboy, she was at Pramana Collective where she worked with Mixing Board founder Sean Garrett. In 2016, she served as a Fellow at the Harvard Wyss Institute for Biologically Inspired Engineering and Programmable Nanomaterials, leading an interdisciplinary team of engineers, artists, industrial designers, and physicists on work bridging the divide between the art and science disciplines.
In this Studio Session, Anna and Sean talk about what it’s like to work at a place like Playboy; why standing for nothing is far more risky than taking a stance; why specific language and nuance is important within big transformations; and, what it’s like to design a plane (really).
SG: Tell us how you found yourself at Playboy. What made that an interesting place for you to go work at the moment that you did? What about your background and experience led to that moment?
AO: Backing way up, I have always been really interested in the representation of women through different means — my literature major focus was representation of women in modern and contemporary literature. I wrote my thesis on the voice of Lolita and the different female characters in Nabokov. If you’ve read it, you know it’s super interesting and sexually charged. It tries to create a gray area around women’s sexuality and representation of women — the tension of that has always been something that’s really interested me, both academically, conversationally, and personally. It’s something that I feel very motivated by in terms of creating change and the fact that we need models of women in our society that are complex and nuanced versus just a physical body or a mind.
There’s a way for men to be both, but there’s not really a way for women to be both at the same time. Because to be one, you have to downplay the other. Whether that means playing the ditz, as you see throughout all of 2000s pop culture. A lot of women were these blonde bombshells that were actually incredibly intelligent and were just playing this act. Or the other way around, where it’s basically becoming more masculine and de-sexed in order to be taken seriously intellectually and professionally. The resulting output is that there’s not really a way for women just to be themselves in a lot of contexts.
I thought Playboy was an extremely interesting brand, because one, they were interested in overhauling it from the inside out and really allowing for that complexity. And two, it was in many ways one of these last major establishment bastions of an old patriarchy. The people they were reaching were the people who were still onboard with what they stood for. So it was this really cool opportunity not only to dismantle or challenge something from the inside out that had been, and still was, very problematic. But also to reach a group of people that if you were starting something new you would never really be able to reach with the messaging that we wanted to infuse into the brand, just because of the way that all of our algorithms and filter bubbles work.
It really was a chance to cross that barrier and break the divide. To have not only a one-way broadcast, but a two-way conversation in the wake of #MeToo with an audience that, in many ways, had good intentions, but was terrified of having these conversations. They didn’t know what to ask, for fear of cancel culture, and being told that for even thinking something they are a creep. It didn’t seem like an opportunity that would come around again. And because my own personal interests overlapped so much, it was very motivating and, in a lot of ways, personally therapeutic for me to not just focus on the big picture, but the details of all of this.
SG: It’s an incredibly nuanced thing underneath a brand that wasn’t necessarily immediately known for nuance. Consider Playboy’s logo, which for people keeping score at home, is one of the most five recognized logos in the world. I would guess that many people would look at that logo, and think, “Yeah, boobs,” right? That’s an interesting challenge.
AO: That was the fun of it. It was this incredibly recognizable, very provocative logo. And then introducing the idea that there could be more to it. In its origins, there actually was a lot more to it, but it had really become flattened. The idea that this thing is self-contradictory was actually really interesting. It fed into my same interests of these gray areas and paradoxes.
On the other hand, just practically speaking, having a logo that’s recognizable meant that the work we did was way was immediately noticed and adopted really quickly. Whereas, like most brands I’ve worked on, it would take at least twice that time for that heavy transformation to be widely understood, recognized, and heard about. My rule of thumb is you need to hit people on the head at least three times, and now it’s probably more like five or six times before they remember it. With Playboy, the first or the second time, people notice it and remember it. So in terms of the transformation, we were able to operate at warp speed.
SG: You came onboard at Playboy after doing some work via Pramana. Your mission was really to reset this brand. What is it like to work at a company where, not only are you in the middle of this huge societal conversation, but you’re seen as the enemy, too. Or maybe seen as an avatar to some others. But at the same time inside the company, it’s not like everyone’s looking at this playbook and going, “Oh, next step is this, next step is that.” How do you calibrate such significant change in real time?
AO: It had its major ups and downs, for sure. There were times where everyone’s confusion, frustration, and challenges were directed at me. I was like, “Guys, I’m not the voice of feminism.” In a lot of ways, I’m just learning about what’s going on in culture and what our audience cares about. I got shot as the messenger a lot. One of the big things that really made it possible was realizing that sometimes people just need to let out the steam. It’s going to come at you, and all you have to do is listen. Once they get it out and they feel heard, then they’re actually very willing to try something new. They want to feel like they’re not being overlooked. Having a lot of one-on-ones with all people at all levels made a huge difference, in particular with the people who are executors. So that they know you understand that you’re creating a more difficult job for them, but you also appreciate that they’re putting more work into it.
Probably the first year and a half of the work that I was doing there, with Pramana and then full-time, was really about going into extensive detail about what this brand transformation needed to look like. Down to our practices on set, the company culture and values, even the way that we would shoot a model. We needed to articulate with examples — this trope of coy women, eyes looking away — that doesn’t show agency. We want eye contact because it shows strength and agency. We had to give directives with that level of detail to all of the creative teams. It really was about codifying a lot of that stuff so that there wasn’t as much interpretation at the beginning, and then having the deeper conversations with people so that then they became able to interpret it, and not have to ask a question every time, or be afraid.
SG: What’s the before picture and what’s the after picture? You walk in and this is what it looked like. After all the work, what do things look like now?
AO: The big reductive version of it would be that the before was really this message of entertainment for men. It’s one gender, it’s one way. It’s voyeuristic, it’s observing, and it’s inherently objectifying. The after was “pleasure for all” which is non-gendered. We were very proactive about representing different definitions of gender, and not being binary in our definition of that. But we were also proactively inclusive of women. Pleasure for all is a much more interactive, involved, and multisensory representation. We took the brand from being this media magazine, where you flip through and look at things, to this experiential brand with many different touchpoints. There were opportunities to learn and engage, have an actual dialogue, and also understand yourself and others better.
SG: Meanwhile, you post a revealing photo of a gay man on Instagram to an audience that is used to seeing coy women looking away. You’re obviously directly running into the conflict there for a reason — to evolve thinking. But what’s the day-to-day action on that? How do you manage that?
AO: Part of it was actively recognizing that there was a group of our audience that was repellent to our new target audience. When we started working on this, our audience was about 92% male and 45-plus years old. And the most conservative of that segment were probably 55, 65-plus, but they were also driving no revenue. The way that our audience was interacting with the brand was reinforcing the negative version of the brand. In order to both bring the age down and balance that gender audience out, we needed to show that we were willing to be controversial, take a stand, and challenge that audience. To really generate true buy-in and demonstrate that this was something we were taking seriously.
We would post things that we knew would be shocking and challenge our old audience to either think differently and come onboard or leave. At the same time, we wanted to celebrate causes and champion messages that were important to this younger, 18–35 year old audience that we were targeting. Part of that was leveraging some of these really iconic, gendered, and objectifying brand symbols, such as the bunny suit, which had always only been worn by very attractive women in largely male-dominated settings. And we challenged the gender of that. We did a really cool and fun photo shoot with Ezra Miller in a version of the bunny suit that really celebrated his gender-queer identity. We did something similar recently with Bretman Rock, we did a digital cover photoshoot modeled after the really iconic Kate Moss photoshoot, Bretman in the bunny suit under a Playboy masthead frame.
We worked with celebrities who had a very deep and value-based following. We championed those values, and brought on that audience as a very well-informed group of evangelists for us. We counted on them to talk about it, to spread the word, to share it, and also to create a deep following. We did this work at Pramana, and we called them our breadcrumbs. The more of these very deep and well-pointed breadcrumbs that we had, eventually they’d start to connect, and that becomes the brand. In so doing, we were also able to really prove that we weren’t this version of the brand that people expected and had written off.
SG: You obviously didn’t walk into Playboy and say, “Hey, we’re going to run this photo shoot of this well-known gay man. We’re going to put it everywhere, and this is going to be our thing now, and we’re gonna lose all these old audiences, and it’s all going to be good.” And everyone high fives each other, the finance people say, “Yay!” Obviously, you had to convince people. People may even intellectually get that you need to make the change, but actually then making the change where you’re actively losing an audience to gain a new one has revenue implications and other things. How do you get from that agreement, to actual action, and then actual change?
AO: There definitely were challenges with the level of risk taking that it felt like. There were probably two things that made it more possible. One was outlining and getting buy-in on the plan in advance, which we did as a team with Pramana. It helped a lot to have a team of outsiders behind it who weren’t necessarily involved in day-to-day politics and were paid to be objective. Getting buy-in across the entire senior executive team, everyone understanding that this is what’s going to happen, here’s where it’s going to feel risky, but here’s why it makes sense. We managed that in advance so that when it happened, and those team members who might be like, “What’s happening. This is scary,” we could be like, “We talked about this. It’s part of the plan, and it’s working.” It didn’t seem like there was a lack of control at any point. That was super crucial and I would apply that to anything else that I do in the future. That was a really good lesson.
The second thing we did was measure and share and those measurements as they were coming in, so that people felt comfortable with us being on track. For example, when we posted the Ezra Miller shoot, there would be a large backlash of negative comments and people unfollowing Playboy. But simultaneously there would be a major spike in our follower growth and in the positive comments of people defending the brand. We would take those things, show them, and say, look, here’s what’s happening. Yes, you’re looking at our Instagram and there are these negative comments. We are frustrating people. But every time we do this, there’s a medium-sized downward spike, but there’s a mirror image, double-sized positive spike. And so yes, we’re losing some people, but we’re consistently gaining more than we’re losing.
We had also outlined more qualitative goals that would show that we knew it was working. Such as when our audience starts defending us or when key celebrities that we know we can’t get, because we’ve tried, are coming to us and want to work with us. There were a variety of bigger picture benchmarks that showed us this is actually effective. So then we started thinking about how we can give our audience tools to defend us? How do we arm them with the information? Because it’s much more believable coming from an audience member than it is from us. How do we do things that show these celebrities that this is a brand they should want to be part of? It gave us other ways of accomplishing those goals, and we really did start to see those things happening.
That was the best part. It seemed like a really lofty goal at the start, but now we’re starting to get yeses where we were getting nos, and we’re getting in-bounds that we would’ve never got. The coolest thing was seeing audience members start to defend Playboy, and explain where there were elements of its history that it had really stood for civil rights, LGBTQ rights, cannabis legalization, free speech — these main causes that we were creating rallying cries around. Seeing that message both getting out there, but also so coming back and being used as a shield. That helped us grow a lot.
SG: It should also be noted that this wasn’t all just because Playboy felt the need to play this different societal role. There was certainly a big transition within the organization, which is tied specifically to the big, huge transitions in media at large. The company was a media company with a magazine, and then it became something else. And over this period, the company went public, so there’s financial things involved here that were not immaterial. So that’s also part of your consideration set as all these things are happening. How does that fit into all of this?
AO: We were fortunate to have the first year really be focused on brand building, which is inherently an expensive task. It helped that we knew this was going to be an investment, and we had very strong and complete buy-in from the Playboy CEO on this being a brand building year. And just the very clear fact that if Playboy continued on its trajectory to date, up until three years ago when we started this — just mapping against the way that culture was moving — it was clear that the brand was becoming both increasingly irrelevant and problematic. There was no real future for this brand as it stood at that time. There was an element of necessity and that was definitely understood.
As we built a new audience, it was important to understand what that audience cares about. How they engage with brands, what they want, what they buy, and realizing there were a lot of opportunities for Playboy to leverage the more positive parts of its history to give that audience what it wanted. To be a positive voice in that conversation and be relevant to them. What we saw generally is that the Gen Z audience really buys products and brands because they believe in what the brand stands for and they wear them as a badge. And Playboy is a perfect brand to be a badge brand because it’s always represented something. So we started evolving what that stood for.
SG: If I’m a CEO or CMO reading this interview, and I run this company or this brand that has gotten a little long in the tooth, it’s not so relevant anymore, maybe a little problematic. I’m going to find Anna Ondaatje, have her come on board, and she’s going to help transform this thing. First of all, do you want to do that stuff? And if you did, what are the non-negotiables for an organization to be able to do something like that?
AO: Most importantly, you have to be willing to do this fully and consistently. You can’t have any contradictions within your business, where you’re saying one thing and doing another or undermining it somewhere else. The way that the world works today, it will be found, and it will topple everything. So you really have to buy into it fully. That’s number one.
Number two is there has to be a willingness and the bravery to take a stand, and to say something that some people are going to disagree with. And to represent that and be okay with the fact that there’s definitely a feeling of risk in that. But it’s actually way less risky than just standing for nothing and doing nothing. That’s basically where Playboy was starting to go, it just becomes less and less relevant and fades into the background. So you have to do it fully without contradictions. Taking a stand and saying things that might feel frightening or controversial, and being brave enough to do that.
I personally would never work with an organization that doesn’t have a long-term view. The goals need to be horizon goals, that is a key part of this working. It’s not just about incrementally increasing our sales month over month. It’s that we’re going to take a big stand, and maybe have a month where we’re investing in that. In the long-term, this is going to pay off tenfold for us. If it’s so focused on monthly or quarterly goals, it actually starts to undermine the larger brand goals. Because team members are inherently going to be incentivized to meet their numerical goals, and it’s death by a thousand cuts. The brand objectives and what the brand represents start to erode very quickly.
SG: You started very focused on brand and brand strategy work. At Playboy, you also took on the comms role. What’s your perspective on comms and PR as someone who came from brand strategy land? How did your perspective of it evolve over time?
AO: It’s a very functional and productive pairing. In any good brand those two functions should be, if not under the same team, working extremely closely. There’s so much overlap that they’re going to start saying different things or having different nuances if they’re not working together. Really good comms doesn’t happen in a vacuum. It comes from meaningful things being done within the company. It comes from having real stories. It comes from a degree of transparency. If the brand, the business, and the comms teams are not working together, you can’t do that effectively and you can’t do that truthfully.
Particularly with Playboy, because so much of the stuff we were doing was extremely nuanced and complex when you dug below the surface, the language we were using was really important. And the language needed to be consistent both internally, externally in terms of our marketing, and what we were saying to the media. The media is like the megaphone for everything that’s happening within the company and you’re going to reach way more people through media and social media than you will with anything else, frankly.
SG: So you were at Playboy for three years. In your last year there, you were doing a lot of creative stuff — can you tell us more about that? Why did you decide to leave Playboy? And what lessons did you take with you when you left?
AO: There was one day at Art Basel in Miami where, for some reason, everything happened on the same day. I woke up at 6:00 AM, went to the airport hangar where the Playboy Jet that I had just designed was landing with Cardi B on it.
SG: You designed a plane?
AO: I designed a plane, and then the plane actually flew and worked! At some point very near the beginning of its life, it flew Cardi B in it. So I woke up and saw on Instagram Cardi B talking about this design that I had worked on, then met her as she got off of this plane. Then I had the really crazy and cool opportunity to give an interview tour to CNBC about the plane. When we headed back into South Beach, we threw this crazy creative, interesting event at Art Basel where we had all those celebrities, that would’ve previously never said yes to us, quite literally asking to be invited to our party. We were getting texts like, “Can Leonardo DiCaprio come? He really wants to be there.” I couldn’t believe that was even happening.
All of these things converged at once. That same week we launched this really interesting and fun higher-end collection around the jet set lifestyle called Big Bunny, which is the name of the plane. It was much more elevated, interesting, and design-forward apparel and lifestyle brand that was personally a lot more my style. All of those things really converged on this one Friday, and I was feeling like we had accomplished so much of what I had started there to do, and realized that maybe it was time for a new equally exciting and scary challenge.
SG: What are you excited to do next?
AO: I’m not sure! I really like sitting between the business and the creative teams and being that translator/ambassador. Developing strategy that both works for the business, but also has extremely creative expressions. I also like these scary, big brand transformations. One of the things that was really interesting, fun, and challenging in a good way about being Playboy, was our goal of going public. There were very quantitative brand goals tied to something that can sometimes be somewhat fluffy or abstract. So it was the definition of a long-term goal that we were working towards that was universally agreed upon. I would love to work with a company that’s looking to go public, to be acquired, or have some big event with very real business implications.
Beyond that, I’m currently just enjoying the break, taking a lot of art classes, doing some fun consulting projects, working with Mixing Board a lot. I’m enjoying the break because it really was an all-encompassing 24/7, three years.
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