Rolling the dice: Jayme Boucher on Roll20’s mission to empower gamers everywhere

Jayme, it’s great to tie-in! For anyone new to Roll20, how would you describe what the company does?
Lovely to catch up, Billy! For those unfamiliar: Roll20 offers a tabletop, character sheets and an entire suite of tools supporting all aspects of Tabletop Roleplaying Games. We provide everything needed to enhance gaming sessions and boast the largest online catalogue of digital and print-on-demand RPGs and play-aids. There’s truly something for anyone seeking adventure!

Where did the idea for Roll20 stem from?
It started as a personal project by college roommates hoping to continue playing Dungeons & Dragons with each other after graduating and relocating. Following a successful Kickstarter campaign, the platform was publicly launched in September 2012 and has been growing and evolving ever since.

Can you talk us through some of those key evolutions from the last 12 years?
Perhaps easiest to see from the outside, we’ve partnered with giants in gaming and entertainment, such as Wizards of the Coast, Paizo, Critical Role, and Marvel to bring the games people love to millions across the globe.

During the pandemic, when most TTRPG players couldn’t meet in person, Roll20 experienced a massive surge in users. Subsequently, we welcomed a new CEO and merged with OneBookShelf – home of DriveThruRPG, Dungeon Masters Guild, etc. This partnership doubled our workforce and led to a more than 20x increase in the number of titles available across our combined marketplaces, encompassing comic books, cards, and fiction – in addition to traditional RPG content. Between our high-profile partnerships and those with the most exciting indies working, we gladly provide access to titles from tens of thousands of publishers, artists, and community content creators.

Huge growth. And has there been transformers in terms of tech in that time too?
Yes, we regularly introduce UI enhancements and rolled out tools like Characters and Dungeon Scrawl last year to make creating and managing games easier. We have multiple additional upgrade projects underway – including a complete redesign of DriveThruRPG, rebuilding our Pathfinder and D&D Character Sheets, and Project Jumpgate: the most extensive overhaul and modernisation initiative Roll20 has undergone since its inception.

Even in my three short years with the company, I’ve been consistently amazed by the improvements the team is bringing to the table – pun intended! – to improve the platform day in and day out; no small feat when continuing to cater to millions of users with uninterrupted service. Oh, and we also have a few *secret* projects simmering we’re not quite ready to announce…

I’ll keep an eye out for those! Digging deeper into the experience, what are some of the elements of an RPG that can be brought to life, streamlined, or enhanced on Roll20?
We offer built-in voice and video support, in-game chat, and digital dice rolling for all games. For GMs – Game Masters – with limited time or those seeking a turnkey gaming solution, we offer thousands of pre-built modules ready to run “out of the box” with minimal setup required.

For those looking for more control: every facet of prep and play can be executed and, perhaps more significantly, personalised using Roll20. We offer a tabletop environment that empowers GMs to construct campaigns from scratch, incorporating maps, player handouts, statted NPCs, monsters, and any other elements they wish to customise.

Our mapping system allows for organisation into folders and employs layers with view permissions and Dynamic Lighting to replicate line-of-sight, perspective, and more. Users can utilise drag-and-droppable tokens, customise doors and windows, hide traps, enemies, and treasure… Essentially, everything one might consider to set the scene for an in-person campaign has been implemented by a team dedicated to preserving and enhancing that experience.

Fantastic. And what do you feel is the value of digital gaming experiences like these?
Many hobbyists, regardless of the activity, acknowledge the challenge of coordinating group gatherings due to work commitments, family obligations and various other ways “life” gets in the way. Roll20 alleviates this burden by enabling individuals to join a game from wherever they may be; the elimination of travel time is a significant advantage when scheduling gaming sessions into busy schedules.

Participating from the comfort of home not only reduces the need for family care in many cases, but also provides solutions for people uncomfortable in group settings or meeting/roleplaying around others. Moreover, it offers an opportunity for individuals with limited mobility or health challenges to fully participate.

Personally speaking – as a socially anxious, immunocompromised individual – I’ve greatly benefited from the ability to connect and play with friends from other states, even other countries, from my living room. My second-ever experience playing a TTRPG was virtually, and I’ve not returned to in-person since.

A terrific endorsement. And do you also feel they can sometimes work alongside the ‘live’ experience?
Regarding integration with in-person gaming, we do understand and appreciate that some people prefer to play face-to-face. Our Characters platform was developed with this purpose in mind, allowing players to create and manage unlimited characters for over a dozen popular game systems. Having them accessible – on any device – at a physical table aids in managing levelling, rolls, and all the calculations involved without keeping track of paper character sheets, notes, or dice.

Diving into the team’s creative process for a moment, what are some key elements of developing a digital tabletop experience?
The most critical element is the people behind the product, who are deeply passionate about what we create and why. My colleagues are the unsung heroes behind millions of play experiences and deserve recognition for everything they contribute to the hobby and community we love.

Behind the scenes of the software and content visible to users are nearly 100 product managers, software and web developers, designers, customer support agents, marketers, analysts, quality assurance engineers, publisher relations specialists, content producers, and contractors… Each team has had to learn to embrace change and adapt to the evolving needs of our users and the business.

Extensive research, user testing and feedback gathering, coupled with iterative design processes, play a pivotal role in the development and maintenance of the platform. Our teams prioritise building relationships with our partners and community, gaining familiarity with various game systems, and understanding the most effective ways to present analogue products to new and experienced users digitally. These foundations are crucial for seamlessly converting content and enhancing the gaming experience for our players.

And how close is the collaboration between Roll20 and publishers when translating their titles onto the platform?
It varies depending on the project scope and type of product being developed. We work very closely with partners for whom we’re building titles from the ground up, particularly when they involve Character Sheets and Compendiums – essentially, digital rulebooks – which are more complex components of gameplay.

For less intensive projects, partners have the autonomy to build and launch titles entirely on their own. Our tools enable them to upload PDFs to DriveThruRPG and Art Packs or Adventures for sale on Roll20 with just a few clicks. Once a campaign or supplement is built on the Tabletop, partners can easily generate a copy to make available for sale to the public once they’re vetted to sell on the Marketplace.

We are continually enhancing the tools that facilitate easier sharing with the community.

Great. Thanks for that. And how ‘big’ does a title have to be to get the Roll20 treatment?
Anyone can sell their products on our various marketplaces, whether they’re an established company or an individual creator. Our sign-up process is straightforward on both DriveThruRPG and Roll20 and designed to be as painless as possible. Community Content programs like Dungeon Masters Guild and Pathfinder/Starfinder Infinite enable creators to utilise the official intellectual property of Dungeons & Dragons and Paizo systems in the content they create and sell and are a great way to create new adventures and supplements for your favorite game systems.

When it comes to official conversions for the Tabletop, our team can provide recommendations regarding the types of digital products that would best represent your game or play aid, and discuss options for completing that work yourself – with the help of third-party contractors, or as part of a project with Roll20 doing the work internally.

Jayme, this has been incredibly insightful. Thank you. Before we wrap up, I should ask, how much does Roll20 cost?
Using the Tabletop, Characters, and Dungeon Scrawl is completely free and works directly in your browser, eliminating the need for up-front purchase or installation. Anyone can easily sign up and start playing immediately, and our Content Team has worked to curate and continuously expand a library of no-cost starter titles tailored for newcomers or those curious about new systems. The aim is to break down as many of the barriers that prevent people from gaming as possible.

For folks seeking enhanced features and benefits, we offer two subscription levels (Plus and Pro) available for purchase on a monthly or annual basis, starting at under $5 per month. Subscribing unlocks features like additional storage, Dynamic Lighting, content-sharing, customization tools, and even free monthly content rewards.

One of the most exciting aspects of the aforementioned Project Jumpgate is performance updates powerful enough to facilitate gameplay on a broader range of devices. This means players can game with their friends whether on a tablet, a Chromebook, or a high-end gaming PC. Not everybody can afford premium hardware, so upgrading our software to meet them where they are is incredibly important to us.

And when it comes to the games?
The price of actual games varies by format and is determined by the individual partners selling on the Marketplace(s). While many offer free or “pay what you want” PDFs – most art or adventures converted for use on the Tabletop start at $4.99 and increase from there. We love that so many of our partners can make a living sharing their creations with our users. We offer daily deals, and frequent seasonal promotions that benefit them and our users – the best way to stay up to date is by following the Roll20 social account(s).

Great stuff. So, for anyone reading who hasn’t played a game on the platform yet, how can they get started?
Sign up for a free account on Roll20.net and check out the Help Center’s Crash Course if you’re looking to learn the basics of the Tabletop. Then, simply start a new game and follow the Tutorial!

There’s no “wrong way” to play – and discovering everything the platform can do for you is part of the adventure since so much of it is based on your preferences and imagination. There’s a wealth of helpful videos on YouTube, and our Customer Experience team is always available to lend a hand!

Thanks again Jayme!

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