Tabletop games are going through a renaissance now, and many of them are going digital. That’s why veteran gaming executive Corey Rosemond has joined Roll20 as its chief operating officer.

The Las Vegas-based Roll20 was started in 2012 to take tabletop games digital. But it doesn’t turn them into video games. Rather, it gives game masters for role-playing games like Dungeons & Dragons the tools to help immerse players in the world of the games. Rosemond has more than 20 years of experience in interactive entertainment

Roll20 specializes in role-playing games and it has added 25 employees in just the past couple of years. During the pandemic, the opportunity has grown dramatically as friends could no longer play tabletop games in person and had to move to online play.

Rosemond brings a wealth of experience in gaming hardware and software to the tabletop industry. As the company continues to expand, Rosemond will help Roll20 improve its offerings and increase user acquisition. CEO Nolan Jones and his college roommates created the company to let people play their tabletop campaigns while away at school, and now it has more than eight million users. Rosemond will help the team figure out better ways to serve that audience with innovation.


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His priorities include the development of a mobile app, continuing to expand and enhance Roll20’s marketplace, and investment in quality-of-life improvements — all projects that will continue to Roll20’s growth. I spoke with Rosemond about his new role.

Here’s an edited transcript of our interview.

Above: Corey Rosemond is COO of Roll20.

Image Credit: Roll20

GamesBeat: What was appealing about the job? Could you talk more about what you’ll do for Roll20?

Corey Rosemond: Roll20 is a leading virtual tabletop company that’s enabling and looking at taking especially tabletop role-playing games online. It’s a platform that adds in features and capabilities for people to be able to enjoy their tabletop role-playing game experience, both online but also, very important to note, to be able to have companion applications that allow people to bring an enhanced tabletop experience to physical, in-person games as well.

As you know, tabletop gaming is something that — I want to say it’s the less flashy aspect of interactive entertainment. One of the things that makes tabletop gaming special and unique is the requirement of human interaction. The game master, if you will. That human interaction, that human dynamic creativity, is something that has allowed and enabled tabletop games to continue to evolve and show an appeal even as video games have completely advanced and increased over the last 20 to 30 years. There’s still this appeal for tabletop role-playing and tabletop gaming in general.

Roll20 started in 2012 as a way for three University of Kansas students to continue their tabletop gameplay even as they moved off in different directions. They did it for themselves. People said, “Wait, that’s pretty cool! I’d like to be able to do that too.” There was this new crowdfunding platform called Kickstarter, and they decided to do a campaign for about $5,000. They raised approximately $40,000 and said, “Okay, I guess we’ll do this.”

The rest has been history. It’s a bootstrapped, profitable company over the last nine years. Roll20 has built that audience, built the community, provided a platform for various creators in the role-playing game space to have that virtual platform that allows people to play their games through an online, browser-based forum.

GamesBeat: How does it compare to other digital tabletop companies like what Asmodee is doing, or some newer ones like Gameboard? You have the augmented reality folks, a variety of productions out there.

Rosemond: What makes Roll20 different is we put a priority on where we feel like the creators meet the players. I think about it in our marketplace, the conversion in the support services we provide to more game creators, to actually create this dynamic experience on the Roll20 platform. That experience is unique compared to a lot of our competitors. We always strive to go above and beyond just taking PDFs and putting them online. We want to create differentiated and unique experiences representing the game online.

When you think about it, we were one of the first platforms to target the fact that the GM/DM is the source of the overall player experience. In many respects what Roll20 has been focused on is building out various tools and various features that enable the GM to enhance their experience, if you will, in terms of setting up the game adventure, having that continuity of interest going on for weeks and months, and in some instances years. We have some games that have gone on non-stop for several years. Knowing that it all starts with those game masters. That attention to prioritizing them, and in conjunction prioritizing creators. They’re creating these experiences and these expansions to the game systems that go on and allow those audiences to have this continuity that you don’t find in any other format of interactive entertainment.

Above: Roll20’s interface for running a role-playing game.

Image Credit: Roll20

GamesBeat: Is this the first time you’ve had a COO role?

Rosemond: This is my first time in a COO role, yes. Previous to this I was VP of operations for the American subsidiary of Nacon. Nacon is a French hardware and software company, primarily in console and PC gaming.

GamesBeat: What felt like you were ready to take on this kind of role?

Rosemond: A couple of things. One, I felt as if taking on a global role at the COO level was something that presented a lot of exciting opportunities for me to apply the learnings from my 25 years in the interactive entertainment industry. Primarily on the video game side, but also both software and hardware. Two, what lay ahead in terms of disrupting and growing the tabletop side of the business.

When I look at the future, when I do my own analysis of what the next generation, call it Gen Z or digital natives — I almost feel like they’ve come full circle, where they want personalized, human touch experiences. Maybe as almost a passive rebellion against the AI everything. They want to go beyond the bots, if you will. They want interactions with other people, by other people. When I think about the entire tabletop space in the tradition of GMs, in the tradition of having that dynamic engagement with someone that will adjust and balance out the gameplay from a human perspective — I believe there’s so much growth to take place there going forward. That’s what led me to look at the tabletop space, the virtual tabletop space specifically, and that’s what led me to role-playing.

GamesBeat: Are there some skills that you think you need particularly in this kind of role?

Rosemond: For the role of chief operating officer, I bring a couple of things in particular. I’m just completing my first 90 days, so I think I can speak to this now with solid first impressions. I feel as if, first and foremost, I go back to my core function, which is product management. I look at how owning the product and looking at defining the product going forward and working from that context, based on my history. Being able to work across the people and the technologies, looking at where we want to take the industry, the segment, via the company and our strategy. Bringing all of that together, supporting the CEO, and also working hand in hand with the leadership team to get the best out of us as a functional unit is the core to the job.

That’s my own personal definition. No two COO roles are ever exactly the same. That’s the one piece of feedback from a number of COOs I talked to across industries, but more than a few video game companies. Almost to a person, they said that it’s a job that wears many hats, so be prepared to wear as many hats as required. For me, like I said, I look at my strategy, biz dev, and product backgrounds, combining those along with the rest of the leadership team. We have an amazing team here, with people from the video game space, the tabletop space, and a number of other industries. But primarily board games, tabletop. Intuitively, they’ve been working at Roll20 so long that they’re truly virtual tabletop veterans. Plus myself and at least one other leader from the video game space.

Above: Roll20 has both mobile and desktop interfaces.

Image Credit: Roll20

GamesBeat: How many people work at Roll20?

Rosemond: Right now we’re right at 60. We’ve been growing significantly. We’ll grow as appropriate in terms of bringing on additional people. We’ve grown quite a bit in the last year, year and a half.

GamesBeat: Has the company raised money multiple times beyond the Kickstarter, or was that the only instance?

Rosemond: The company is proud to say that beyond the initial Kickstarter campaign in 2012, it’s been completely self-funded, bootstrapped.

GamesBeat: Do you talk about revenues or any other indicators of size?

Rosemond: We’ve not talked about revenue, being privately held. We’ve shared that we have a membership north of 8 million. We’re looking forward to being able to announce, at least on our Roll20 blog, when we hit the 10 million mark. We’re approaching that milestone. But I can publicly state 8 million as of today.

GamesBeat: As far as guidance for people in a similar career track, what sort of advice would you have?

Rosemond: My advice would be — as we look here in 2021, there’s a lot in terms of social consciousness and justice. There was a lot of attention that I, at least, heard about in the Kotaku article where Phil Spencer talked about the dearth of black leadership within Xbox historically. That one hit home, frankly, because I used to work at Xbox. I had to think about that.

What I can say is, acknowledgement that there have been people from a variety of underrepresented minority groups — not just Black, African-American, but Hispanic, Native American, others — there have been challenges for women and for the LGBTQ community within the interactive entertainment space. I can tell you, from my 25 years, it hasn’t always been the straightest path. There have been a lot of challenges, some overt and some covert.

The good news is that for me, I remained committed to this industry, because I love it. I absolutely believe that the interactive entertainment industry is one of the best in terms of what we provide end users, which is true entertainment, on their terms, in an interactive capacity that’s not just passive, like watching TV or going to the movies. You get to engage yourself. That’s what’s kept me in the industry despite great opportunities to go elsewhere. Given that experience, given a collective of experiences, that’s why I’ve stayed in it.

But at the same time it’s why, for me, at this point, coming into a virtual tabletop company was a great evolution for me. I have a lot of video game experience, having worked at Microsoft and Xbox, having worked at Plantronics in creating the Rig brand, having worked at Dell with the XPS gaming platform, and HP with gaming there. I’m able to see what I feel to be another hyper-growth segment of interactive entertainment. Right now that’s tabletop. I look at where mobile was 10 or 15 years ago, where PC gaming or casual gaming was 20 years ago. I’ve been part of all of those hyper-growth situations.

I’ll face up to it. The pandemic got a lot of people to re-evaluate how they engage with gaming overall. That combined with Gen Z and digital natives wanting more personalization. It’s quite significant. We’ve all talked about this. I’ve attended the last couple of GamesBeats. As we think about the metaverse, I think about it as lending itself to where we’re at with GMs and human-led adventures, human-led interactions within interactive entertainment. What I mean by that is, as we look out now at role-playing games, that’s going to lend itself quite well to the metaverse in my opinion.

It’ll be one thing to have players versus the environment, versus the environment’s AI, which is traditional in most video games. But to actually have that GM-led experience, that episodic content, something more like taking a true adventure with someone, following someone’s adventure, being part of that with the human on-the-fly dynamic. That’s the exciting part to me.

When I think about where we’re headed next, right now we’re starting with virtual tabletop. We’re looking at companions with the physical space, because we still do believe — there are people who just want to go have that physical gameplay interaction. We want to be able to support that as well. But looking to the future, and by that I mean five years and more, I see a place where this genre of gaming is going to lend itself to what today is being described as the metaverse. We’ll see if that name sticks in five years.

The prerequisite, always, when I look at the space Roll20 is in, is the human interaction. It’s all about how we provide the best possible platform for those creators and GMs that want to establish these adventures, establish these experience, for those one to five or however many players are going to participate within that adventure.

GamesBeat: When it comes to diversity, what is your hope for the industry? How can it get better?

Rosemond: I’ll be frank with you. My hope with the industry is that a lot more interactive entertainment companies can look and act like Roll20. When I look at it from an underrepresented minority perspective, we’re approximately 25 percent diverse in the organization. It’s very high. It’s diverse both from underrepresented minority perspectives, from a woman’s perspective, much more than I’ve seen in the game industry.

Most important, it’s across disciplines. As I look across the organization, we have truly diverse representation across the board. Dev, finance, operations, customer experience, HR, program management, QA. We have a truly inclusive and diverse organization across functions. Not just in one or two traditional functions where there’s been more diversity than in other parts of organizations.

That’s something that attracted me as I went through the interview process. This is a company that gets it. This is a company where, frankly, people are self-aware. They’re constantly, continually working on how we can be both more inclusive, but also successful and productive and competitive as a company. It’s not something here that’s just being done to hit a metric, to be able to raise a flag and say how woke we are as a company. It’s something that’s truly working, something the company believes in. It gives us a competitive advantage.

Above: Roll20’s desktop interface.

Image Credit: Roll20

GamesBeat: Where would you like to go with Roll20? Where do you think there’s room to grow or room for improvement?

Rosemond: In terms of room to grow, I want to enable and unlock the potential for us to delight and to train the imaginations of all the untapped people, in my opinion, that haven’t understood the full experiential value of what tabletop and role-playing games represent. A lot of people only think about role-playing games through the lens of Dungeons & Dragons, to use one example. It’s the leader, so I use it. That’s so far removed from what is offered and what’s available within tabletop role-playing games.

I’ll give you an analogy. That’s like saying the entire video game world is based on World of Warcraft. For a time it was revolutionary, and it was predominant in many respects, but — I use that because when I think about the mainstream, given the South Park episode, or a couple of other sitcoms that brought up video games — in that time, in the 2000s, they only talked about World of Warcraft. That’s what video games are about, that one game? There are literally millions of games out there, but everyone thought, that represents a video game. Or Halo. Or Madden. Or Grand Theft Auto. GTA is probably an even better example. People thought, “That’s video games.” When politicians talked about video games they’d bring up five examples, max.

Now mainstream people have figured out, primarily due to mobile games, but also due to casual PC games, that gaming is much more diverse than that. I’ll never forget people telling me that they’re not gamers, while they’re literally on their phone playing Candy Crush. That’s a game. You’re a game. “Yeah, I guess so?” In much the same regard, you have role-playing games and tabletop games, and people don’t even realize that many of them have nothing to do with a fantasy world that resembles Game of Thrones or Lord of the Rings.

Mind you, those are very popular. But I just played a game called Alice is Missing on our platform. The best way for me to describe that game is almost like Riverdale meets 90210. Or Dawson’s Creek. Playing this game, it’s meant to be a four-hour game, and at the start I’m thinking, “What are we going to do for four hours?” Next thing I know three hours and 30 minutes have passed, and we’re in the middle of this. We’re caught up in the adventure. You find yourself having a great time. I just flies by. I had a lot of fun with this game, and there are no weapons, nothing like that going on. But it’s a truly engaging adventure. It reminded me of watching an extended version of something like Dawson’s Creek or Riverdale. I found myself having an experience I’d never had before through other types of interactive entertainment. I’d venture to say that with more than 900 gaming systems on Roll20 today, right now, that there’s a tabletop game for everyone.

Going forward I see us expanding that. We’ve been working with a lot of role-playing game creators to enable them to get their games and their creative endeavors out to a broader set of people than ever before. If you think about it traditionally, to make a board game you need a lot of up-front cash. You need a publisher to get that game printed and positioned in a Target or a Wal-Mart. Then, fingers crossed, your marketing is spot-on and you find an audience and you’re able to grow from there.

What Roll20 represents is the best possible way for those developers and content creators and designers to get their games out to the audience online, right now, without depending on the physical side of the business. We will keep growing the better we can connect the untapped millions of tabletop gamers out there — or unknowing soon-to-be tabletop games out there — with these great creative endeavors that designers and creators are coming up with on an almost daily basis.

One more figure I can give you. More than $230 million of Kickstarter money that’s funded projects has been for tabletop games. There’s a lot of creativity out there, a lot of games being created, that are traditionally more tabletop games. We enable those games to be played online. If you look at some of the leading Kickstarter campaigns out there, we participate. If a game is funded, you may be able to play that game sooner than the physical version arrives on Roll20. That’s something we’ve done with a number of publishers and developers of tabletop games.

GamesBeat: Sounds like fun.

Rosemond: It’s been good trouble in terms of the work and getting myself onboarded. I’m looking forward to the future.

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