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The Marketing Agency Leadership Podcast

Jun 3, 2021

Will Cady heads the Creative Strategy Team at Reddit, which he describes as a platform of more than 100,000 different, intent-driven, purpose-driven communities representing 100,000 distinct cultures . . . and an “incredible petri dish of niche subcultures that are emerging and influencing or becoming mainstream culture.” He says that “people go to Google to search for information . . . and to Reddit to search for what other people have found.” 

Reddit’s Creative Strategy team sits between these “very curious” subculture communities and the brands that want to find their place in these communities. Will says the Creative Strategy Team’s mission of “turning curiosity into understanding” runs both ways . . . 1) brands need to understand the different cultures on a deeper level to know what is coming in the future and 2) Reddit need a deeper understanding of the brands and how they meet cultural needs of the different communities.

He explains. “Brands are made up of humans” and, when these humans tell a story, they gain the ability to build powerful connections and customer trust. He says Reddit is a place where brands can be proud, vulnerable, ask forgiveness, explain changes in how they do business, find out what customers want . . . and to bring something to a community that was never before available. He says marketing today is not “going in the direction of building trust” . . . Building trust is already a critical component of today’s marketing.

Reddit is best known for the AMA, where people present their “positions” and invite people to “Ask Me Anything.” For brands, an ad looks like any Reddit post, but is delivered to an audience of people who go to pre-selected communities. This “promoted post” can host text, an image, a GIF, or a video.” The upvote and downvote mechanism is optional. Comments can be on or off. Will uses origami as a metaphor for this, where the promoted post is the piece of paper . . . which can be folded into any shape. A brand can engage Will’s team to create promoted posts. However, the platform has been built to be incredibly rich in capabilities, but at the same time, simple, for those who want to go the “do-it-yourself” route. 

The opportunity to use promoted posts to research market trends or test user perceptions is huge. Will provides this example: Chipotle had observed the variety of trending diets (paleo, keto), announced that it was developing “Lifestyle Bowls,” asked the groups following these diets what ingredients they wanted, and then launched the bowls, thanking those who had commented for helping to make the product “right” . . . with resounding success. 

Will’s personal history touches on music, mysticism, and marketing, all of which, he says, center on knowing, studying, and playing with what moves people. In addition to leading the Creative Strategy Team, he teaches meditation, reads tarot cards, and jams with musical groups . . . a bow to his 15-plus years as a professional musician. He used Reddit as his “secret weapon for learning” and a way to promote his music long before he took his first position with the company. He says the Reddit of the years from 2013 to 2016 “felt a little bit more like a Wikipedia or a Craigslist . . . (a) ubiquitous part of the internet, but it wasn’t a business.” When he started working in sales at Reddit, the company did not have a viable ad product . . . the new and very small sales team had to build it. 

Today, Will sees Reddit as a hybrid of tech and media, a bellwether of social trends, and a place for brands to build relationships with their customers. In order to move forward into the future, media, tech, marketing, and businesses in general will need good answers to three questions: 

Why are we here? 

What are we doing for humanity? 

What are we doing for the world?”

Interesting questions for all of us.

Transcript Follows:

ROB: Welcome to the Marketing Agency Leadership Podcast. I’m your host, Rob Kischuk, and I am joined today by our guest, Will Cady. Will is the Head of Creative Strategy at Reddit, and Will’s based in Los Angeles. Welcome to the podcast, Will.

WILL: Thank you. Thank you for having me, Rob.

ROB: I think everybody probably listening understands and knows Reddit on some level, so I think it would be interesting to understand your role within that Reddit world.

WILL: The creative strategy team at Reddit, our mission is we turn curiosity into understanding. And Reddit, if nothing else, is full of curiosities. As a platform with over 100,000 different communities representing 100,000 distinct cultures, it’s proven to be this incredible petri dish of niche subcultures that are emerging and influencing or becoming mainstream culture.

What the creative strategy team does is we sit in between the community and the brands that want to activate and find belonging, find community on this platform, and we really provide understanding going both ways – understanding for those brands to look at all of these different cultures and understand them at a deeper level so that they can find their place, they can understand the future that’s coming, and then also Reddit user behavior, they’re very, very curious. They seek. They don’t scroll. They’re there for a reason. We want to pair that curiosity with a deeper understanding of the brands when they come in to talk about how their products, how their services are really meeting the needs of the cultures of the different communities that people are a part of.

ROB: That’s a fascinating place in the ecosystem. I love how you said that people seek. It really resonates with my own experience with Reddit. There’s a lot of sites that you can go to and if you’re not logged in, you don’t feel like you’re missing much. But if you’re not logged in on Reddit, I feel like you’re missing the world. It’s not even like some sites where they feed content to you and you feel like you’re being fed to an algorithm. It really is feeding curiosity.

I think it would be interesting for us, Will, also to understand – I think you have a very interesting journey at Reddit yourself. Talk about how you came into this wild world of Reddit and what your own career path has been within the organization.

WILL: It’s a long and winding and strange journey. My career, by my expertise, I sit at this strange nexus point between music and mysticism and marketing. Today I’m leading the creative strategy team, also teaching meditation, doing strategy reports, doing tarot readings, all of the above, jam sessions and whatnot. For me, they all actually really come together in a very coherent way, which is not expected, but it’s interesting.

You look at music and marketing and mysticism. You look at all of these things, and really what they are at their center is knowing what moves people and studying what moves people and playing with what moves people.

I spent about 15 to 20 years as a professional musician, building a meditation practice and all that, and when I moved from Boston to Los Angeles, I started to realize when I stepped into digital media at a music publisher magazine that there was a lot I had to learn about what resonates in culture. What actually catches and reverberates and becomes movements, becomes these really big mainstream cultural ideas. I got really, really fixated on that. I started to really longform my experiments with this.

And I would always go to Reddit. Reddit was kind of my secret weapon for learning. It’s how I discovered teachers like Alan Watts. It’s how I promoted my music into different communities that utilized some of these audio lectures from Alan Watts. I saw my music videos go to the front page of Reddit All, all the time, and really drive hundreds of thousands of listens in a moment.

As a marketer, I would always think, how can I understand what we’re really trying to achieve here through the lens of the communities that this brand is trying to reach on Reddit? And then if I’m really lucky, how can I find a way to get this content that we’re creating for this brand in front of the Reddit audience?

At that time – this is about 2013 to 2016 – it’s surprising how different media was, even really not that long ago. But looking narrowly at Reddit, Reddit felt a little bit more like a Wikipedia or a Craigslist. It was this ubiquitous part of the internet, but it wasn’t a business. It wasn’t something like a Facebook or a Twitter.

I saw that Reddit was starting to hire some folks, and I knew. I knew that there was this incredible power on the front page of the internet that a lot of people around me in the media industry didn’t really understand. So it was really a no-brainer for me to take that job, and it was an exploratory role. It was like, let’s see what the Los Angeles market can be and do for Reddit.

I started as a salesperson, and I was one of a very, very short list of people representing Reddit in a massive market. We basically said yes to every email and phone call that we got. We took all the meetings. We found that Reddit has a lot to offer everybody. If you want to do an AMA, you want to do some research in terms of market trends or user perceptions – all of these things that are around advertising, Reddit has value to add.

We didn’t have, really, a viable ad product in 2016. We had to build it. We’ve built a great platform now, but in that time in between, we really had to tell the story: “Listen, this is the most influential audience on the internet, and your brand’s got to at least be listening to it, if not speaking to it. So let’s keep talking. Let’s figure out a way to build a partnership.” That became the basis of the playbook that is a massive part of the brand partnerships operation and is serviced by the creative strategy team.

ROB: It’s interesting; you started down this path. You mentioned the AMAs. When a marketer wants to think about the entry points to marketing on Reddit, obviously there are organic avenues – which you may enter at your own peril. When it comes to you, your team, what sort of entry points are possible on a self-service approach and what kind of entry points are a little bit more structured?

WILL: The AMA is a really good metaphor for how to do Reddit in general because it’s a conversation. It’s a dialogue. You’re coming to the platform, and when an AMA is happening, it’s a live experience. It’s an exchange between you and the community, and it’s really based on this idea of being human. There’s this thrill.

It’s so funny that it was so massive on Reddit so early because even though it’s text-based, it’s very fresh and relevant to some of the experiences we have right now where if it’s a celebrity – John Boyega or Chris Pratt, Hosier, some of the AMAs I had the privilege to work on – the users in that thread were just so excited that they were on the same URL as somebody that they really admire and respect. You’re working with that kind of excitement to create a moment of remarkable connection that feels really authentic, vulnerable, and human, and is not the kind of thing that you would typically see in a press junket. It was unexpected and it was different and it defied the way that things felt for fans before.

Today, we do that with brands. The big truth here is that brands are made up of humans, and when the humans behind the brands show up and they tell a story, it’s a moment to foster a very powerful connection that builds trust. Brands have a place where they can be proud, they can be vulnerable. We’ve had brands come to us and say, “We have a Super Bowl commercial. Let’s talk about it.” That was the first time anybody on Reddit could say “I have a Super Bowl commercial.” That’s a moment where brands are bringing something to the community that the community of people couldn’t bring to themselves beforehand, and it created this excitement.

We’ve had brands come to the community for mea culpa. “We’re making a big transformation” or “We’re trying to explain what has transpired over the last couple of months.” It’s an opportunity to meet human to human, to recognize that there are human beings on other side of that keyboard and build trust from there.

This is really where marketing is – not even headed, it’s where it’s at right now: thinking about building trust. The AMA has been around for a long time, and it’s elegantly simple. Ask Me Anything. It represents the blueprint of everything that you can do with platforms like Reddit.

ROB: And it’s so helpful to have a coach like your team as someone’s heading into that. So the AMA is one of those ad products that’s available; what’s the range of ad products that are available to a brand who’s thinking about marketing on Reddit?

WILL: This is interesting. Talking about the team, the creative strategy team is incredibly sophisticated at these things. They’re so sophisticated that they make it easy. That’s the important lesson that I’ve definitely learned on my path. Reddit has such a depth to it that there’s so many exciting things you can do, but it’s really remarkably easy, and you’ve got to start with what makes it easy. That’s the focus of the creative strategy team. We can drive this thing at 150 miles per hour if you want, but let’s start at 20. Crawl, walk, run. Let’s do some interesting engagements here.

From an ad standpoint, the atomic unit is called the promoted post. It looks like a Reddit post. It can host text, it can host an image, a GIF, a video. You can have comments off, you can have comments on. It’s got the upvote mechanism, the downvote mechanism if you want to use that and get a great signal. And it looks and operates in the same exact way as any post on Reddit, the only difference being that through the targeting, you can control who does and does not see that media.

The way that I look at things from the creative strategy team is through the metaphor of origami. [laughs] The promoted post is a piece of paper, and we make cranes, we make boats, we make all manner of different things out of that simple piece of paper. That’s the AMA. That’s the megathread, which is a vast, longform bit of text that explains all of the product details. Really great for our car buyers and our computer buyers and our tech audience. We do conversation posts where we do something like a writing prompt, where we co-create with our users. We put web comics in there. We put videos in there and GIFs and memes. But it’s all one ad unit. So it’s elegantly simple with the potential to be staggeringly sophisticated.

ROB: When someone’s thinking about getting into this atomic unit of a promoted post, is it something they can dabble in self-service? Do they need to engage with your team? There’s certainly advantages for that sometimes, but can someone dip their toe in the water and fire up an ads account and a credit card? Or is it more complicated than that?

WILL: They absolutely can. We have a self-serve platform, an ads manager. You can jump right into the promoted post and you can select your targeting. It has great parity with the kinds of ads managers you’re going to see on other platforms. We’ve spent the last 3 to 4 years really investing in building that, and it’s a great way in.

ROB: It certainly sounds like it. When someone starts to think about how to do well on this, one thing I think we’ll think about is targeting. How should we think about targeting? What’s the menu of possibilities? Are you looking mostly at targeting people who follow a certain subreddit, people who have commented? What’s a good targeting campaign look like?

WILL: That’s a great place to dive into now because the ads manager is going to look like what you experience elsewhere. You’re going to be able to target based on interests, but what those interests are constructed by is slightly different than what you have elsewhere. It’s not a social graph. It’s not based off of people’s identity, their information. It’s based off of the communities that they go to. It’s a community graph rather than a social graph.

So if you have the interest category of auto enthusiasts, for example, that’s going to serve your ad to people that are engaging with a constellation of subreddits like “What car should I buy?” or the Toyota subreddit or the WRX subreddit. Everything from the broad interest in cars to the make and the model.

And Reddit has something that is also really remarkable here when it comes to this kind of targeting, and its intent. When you look at a community like “What car should I buy?”, when somebody’s engaging in a community like that, they’re not just interested in cars. They have the intent to buy a car. They are in the market. They are looking for that information. We have intent-driven, purpose-driven communities for everything imaginable – for vacuum cleaners and climate change and everything in between.

ROB: I’m so glad you mentioned intent because that was certainly in the back of my mind. When you’re talking about users following subreddits, it reminds me so much of the power that has made Google search so powerful for so long. It’s always been that someone was intentional in what they were searching for, and you weren’t just slicing demographics 10 different ways. It’s really piquing my curiosity in a big way.

I think something that leads us to that marketers should probably think about: what should marketers not do when they’re entering into the world of marketing on Reddit?

WILL: I love that you brought up the similarities with Google there. If Google is where you search for information, Reddit is where you search for what other people have already found. We’ve found that when it comes to the trust that people have in the information on products and news, Reddit was closer to Google than it was to the rest of social media in terms of scoring tremendously high on the trust that people put into that. Because it is a resource that people use for information.

It’s hard to find information that you can trust online right now. Reddit is a place that verifies through other people, like “Here’s my actual experience.” So whatever that life moment that you go through – and I myself have gone through so many in the last couple years; I’ve gotten married, I’ve gotten a home, I’ve gotten a juice machine. [laughs] In each of those scenarios, I was using Reddit for my product journey to really figure out, what can I trust when it comes to learning how to go through this passage?

For brands, I think they’ve got to really be cognizant of the role they should play in meeting people on that journey. There’s value in simply being there, just knowing that Reddit is on the path to purchase and that there’s an incredible amount of consideration that people are putting into that path when they’re on Reddit. And just show up. Just show up and wave your hand and say, “Hey, happy to be here. This is our product, this is our info.” It’s super simple. You can take your marketing that you’re using in other channels and put it in the right place at the right time, knowing how important this platform and this audience is. And don’t overthink that.

Then beyond that, it’s an opportunity to really engage. Once you’ve gotten some signal, place a few different bets, a few different targeting cohorts that you set up with your creative. See what’s resonating. Maybe you might be surprised, actually, at who’s engaging with your ads. Maybe it doesn’t actually match your expectations. That might be a way to step into an intersectional audience that is really an opportunity that you hadn’t considered.

Begin to have a dialogue with them. Turn the comments on when you’re ready (you can start with the comments off). Have a prompt and bring the humans behind your brand on board. Say, “This is our R&D team. We’ve noticed that you’re changing the way we think about vacuum cleaners, the way we think about home gardening.” That’s a huge space for transformation right now. Have a conversation. Show up authentically and really be there for them.

To provide a story and a case study here, that’s exactly what Chipotle did a couple of years ago. They released the Lifestyle Bowls, which were based off of the cultural observation that all of these diets were emerging, like the paleo diet, Whole30, keto, etc. We have communities for each of those, and they’re robust and very, very active. So Chipotle with their ads, they turned the comments on and said, “We are making lunch items for your diet. What should we put in it?” They stayed in that conversation and they had a back-and-forth. When they came back around, they were able to say, “Lifestyle Bowls are out and you helped us know how to make them right. Here they are.”

And the trust they earned was incredible. The call to action was very, very powerful because all of the Redditors who had participated in that said to their coworkers, their friends, their family, “We’re going to lunch at Chipotle because I’ve got to try this bowl that I had a hand in creating.” It created a cultural moment in these niche subcultures that, as the tide rose on all of these different diets, Chipotle’s Lifestyle Bowls rose with them.

ROB: It’s interesting that you mention that because Chipotle with those bowls – they actually come across as quite authentic all the way down to the store. I was at Chipotle a month ago and they had cauliflower rice, which I imagine is part of this, right?

WILL: That’s where that mission statement of the creative strategy team comes into play. We turn curiosity into understanding. At first it’s like, cauliflower rice? That’s a curiosity. It’s strange. But then when you understand the reasons for that and where it comes from and how it fits into culture, it shows itself to be a tremendous opportunity.

So what we want to do is highlight things like that early and often so that our partners have more time to develop their products and their marketing and be agile in the moment when things like that really come to bear.

ROB: All the way down to the store, that entire initiative feels very authentic, very – not to say this inappropriately in a food context, but it feels organic. It just feels right. So it’s awesome to see that stemming from the Reddit ecosystem.

When you think about the different communities – obviously this has been a big year for Reddit news-wise. You may be tired of talking about it or you may not be, and it’s not as much in the moment right now, but the entire Wall Street Bets, GameStop, crypto rotation – there’s a few news cycles on that alone. What’s interesting about that is it’s not that that movement started this year; it’s that that movement became visible this year.

Are there some other communities that you think are maybe waiting for that moment? Are there types of conversation that you think might be driving a news cycle next month?

WILL: I’m not tired of it. I’m grateful for it because it revealed a 10-year-old secret to everybody, which is that Reddit communities are staggeringly sophisticated and influential. I’ve been telling that story for a long time, and now I have a story that everybody recognizes and everybody has the full context on. Before, I was telling the story of McDonald’s and Szechuan sauce and the Rick & Morty community, or the March for Science, or some of the fundraiser for Doctors Without Borders, or when Reddit flooded a hospital ward with pizzas for a young cancer patient.

All of these really remarkable stories of Reddit doing exactly this for over 10 years, and now there’s one that really has become the shorthand, where everybody saw and understands, I think in a very intuitive way, the power of Reddit. That’s what GameStop and Wall Street Bets really represents. It’s the power of Reddit on the world stage. And we know that it’s going to happen again because this is Reddit doing what Reddit does. It’s very well-spirited. It’s the human spirit, and it’s so important for the voice of communities to be able to influence culture in this way for the decades that are ahead of us.

I think that there are quite a few communities right now that we can expect to see some similar kinds of moments from. It’s rarified that you’re going to have something that reaches the kind of stratospheric level of the GameStop moment because it was just this revelatory moment. But I think that what was learned by communities and the broader web and culture is that there are really powerful ways to vote with your dollars that we kind of understood as people beforehand, but now we have tools that we didn’t have beforehand to really have a collective impact together.

So I think we’re going to see different versions of people voting with their dollars together in other sectors that are going to be really, really interesting. In a lot of what we saw with that, people were just throwing one dollar or five dollars into the pot or something like that, and there was this sense of collectivism and what we can do together. We’re going to see that I think in a lot of other areas.

I also think there are some more subtle shifts that are coming. I’ve been keeping an eye on the sustainability communities on Reddit for some time, and there’s a whole underbelly of people that are raising their own chickens and making sourdough and growing vegetables in their backyard, and it’s emerging into this – I always look for the language. I really like this community called Zero Waste. It represents an idea that I want to live a life that is not producing any waste. It’s an aspirational lifestyle in a totally different direction than what we considered beforehand.

This community was having a discussion earlier this week about whether or not brands belong in a community like this, and how they felt about seeing brands move towards product packaging and messaging that at its best is contributing to the cause and at its worst is what you would call greenwashing. There’s an example of some soap company that had paper packaging for the soap, and when you peeled back the paper there was a plastic container on the inside. [laughs]

The sentiment that came through in that community was that they really want brands to be a part of this. They’re really, really encouraged to see that brands are stepping into changing the way they manufacture their products, that they’re making pledges to support things like community gardens and all of the different circular systems that are going to save our planet and going to save all of us. They know that brands have influence. They know that brands have resources and power, and that can really shift things the way they like to see them.

So I think we’re going to see that influence not be one of those dramatic spike moments that Wall Street Bets was, but I think over the course of the next 10 years, it’s going to be this protracted rising tide that is going to shift the way that we all think. I think that term, “zero waste,” is going to be very obvious to all of us in the future. But it’s very clear to just a niche subculture on Reddit right now.

ROB: It’s going to be probably interesting. What strikes me about Wall Street Bets is you have this intersection of democratization. You have this democratized community on Reddit, but then you have the democratization of finance, and you have these apps where you can fire up an app and make an investment.

At the intersection you’re talking about with zero waste, there will be some communities who will – you’ll probably be able to buy carbon credits and point them in places you can’t think about right now. Some communities on Reddit will love that and use that, and some will hate it. You’ll have all pieces of that out there. It seems like looking for areas where something tangible is being democratized is maybe a good place to keep an eye on Reddit. 

WILL: Yeah. I don’t know if we’ve got the time to really dive into the depth of this one here, but the very nature of the way we exchange value is changing. The digitization of currencies is supporting that, and there are currencies that belong to communities; there are currencies that belong to causes. All of that can facilitate a moment where the two things I described come together. You have a purpose – zero waste, sustainability – and you have the realization of the things that we can do when we vote with our dollars together. Those can come together and create real change in the world, and we’re going to see that over and over and over again.

ROB: And Reddit’s been in the middle of that for longer than most with Reddit Gold and all that. It’s interesting how long it’s been hiding in plain sight on Reddit, is what I would say.

WILL: Isn’t it? It’s crazy. [laughs]

ROB: I think there’s one other interesting thing to pull on. Reddit has this legacy of being – it just feels techy. It may have been unapproachable for some, but now so many digital natives – you’ve been at this forefront of – this is true in a couple of cases – Silicon Valley mindsets meeting the LA media landscape. That cultural alignment, what does that look like over time? How has it evolved in your time there?

WILL: Wow. The LA/San Francisco connection is a really, really interesting one. There’s a dynamic between tech and media. When I first started, it was like this denial that media could act like tech and that tech could act like media. Vastly, vastly different things. I would say both industries were kind of looking down their nose at each other.

Over the following years, they’ve really seen a tremendous amount of interplay on the level of how the funding works and how the talent is hired and how the products are developed, and of course, the user bases. Is Netflix a media company or a tech company? It’s really at a place right now where we’re understanding that tech and media are very, very much a hybridized thing. 

I think over the course of the next few years, that element that is very, very present in marketing around purpose and intent is going to come in. There are so many options when it comes to our media and there are some many options when it comes to our platforms that all of these businesses really need to think about their why and about the intent of their brand and the intent of their users, and build against that.

I think there are other centers than San Francisco, New York, and LA that are really ahead when it comes to thinking about why. They’re unexpected because they’re different voices. The voices of sustainability, for example, are not coming from metropolitan cities. They’re coming from places like Hawaii. They’re coming from different mindsets altogether. That’s I think a really, really exciting place as the soul goes back into business. Media and tech, for them to find their place in the future, and for marketing to find its place in the future, they have to have a good answer in terms of “Why are we here? What are we doing for humanity? What are we doing for the world?”

ROB: Wow. It’s such a great point to bring it down to. This has been a tremendous privilege. Thank you so much for this grand tour of how to think about Reddit for marketers, what the options are, and how to do so thoughtfully. I think the authenticity of the brand comes through in how you and your team are thinking about these things as well.

WILL: Thank you. Thank you for giving me a platform for my voice. I appreciate the time. 

ROB: Fantastic. Have a great one.

WILL: You too.

ROB: Bye.

Thank you for listening. The Marketing Agency Leadership Podcast is presented by Converge. Converge helps digital marketing agencies and brands automate their reporting so they can be more profitable, accurate, and responsive. To learn more about how Converge can automate your marketing reporting, email, or visit us on the web at