How Late Checkout adds a human touch to async work

Theo Richardson thought he was destined to design shoes. A self-professed sneaker-head, he spent years filling sketchbooks with his ideas—until industrial design school changed his mind. Shoes, he soon discovered, were just an entry point for what he really wanted to do: create concepts for new products, and then help people bring them to life.

At Late Checkout, that’s precisely what Richardson now does. The digital design agency specializes in creating community-based products; think apps and services built on relationships, both with and between users. They count Fortnite maker Epic Games, Warner Music Group, Reddit, and Shopify among their clients. As a product manager, Richardson leads a pod of two product designers who help companies come up with new ideas and then builds them a prototype in as little as 30 days.

“We work extremely efficiently,” Richardson says. “We have some really, really, high caliber folks on the team who can get this stuff done really quickly.”

That’s due, in part, to another of Late Checkout’s strengths: founded early in the pandemic, the company has always been fully remote. This not only lets the company work with top talent from across the world, but makes it possible to spread tasks across time zones, too. And when they can’t chat face-to-face, communication tools like Dropbox Capture help Richardson keep everyone engaged and on the same page. “Having an async strategy is crucial for a company like us,” Richardson says.

The types of companies that Late Checkout works with can vary, from startups to big incumbents. Typically, they’re interested in how they can build products that leverage the latest technological trends—but they also know that, in this day and age, technology alone won’t set them apart.

“We think community is the best moat,” Richardson says. “The product that’s going to win is the one that cultivates the strongest community.”

A more meaningful way to communicate

There are three phases to a Late Checkout project. In the first phase, Richardson will work on an initial concept and pitch it to the client. In the second phase, the team will start on wireframes and product design. By the third phase, they’ll have a working prototype for the client to review—and hopefully develop into a fully-fledged product.

At each stage of the process, clear communication between colleagues is key. Richardson is based in Toronto, while the designers on his team live in Nigeria and Indonesia. Coordinating schedules can be tricky. When meeting live for a video call isn’t possible, tools like Dropbox Capture have been a huge help, making it easy for the team to send short video messages and screen recordings of their work. A designer might use Capture to send an update at the end of their day, just as Richardson is starting his. Or Richardson might send the latest client feedback to his designers while they sleep, so it’s waiting for them when they wake up. 

They could just as easily send these updates as Slack messages or emails—but Richardson prefers the visual and emotional texture that only video can convey. He loves that he can use his hands to express himself, and the intimacy of being able to show someone what he’s talking about on screen while he’s also on screen. He can use more words and convey how he’s feeling with his tone of voice. “Those textural elements really come through and they really help,” he says.

For example, when his team gets great feedback on a project, Richardson wants them to actually feel it in the way he passes the news along.

“If you type out, ‘the client was stoked,’ versus [saying] ‘Whoa! Guys, the client was stoked’—and you're using your hands and using your tone of voice—the message gets conveyed in a very different way,” Richardson says. “I think it's a more meaningful way with a video on Capture.”

He also sees Capture as a valuable tool in his remote work culture-building toolbox. Richardson frequently uses async videos to motivate, inspire, and energize colleagues for whom opportunities for live syncs might be slim, and appreciates that he can see the energy around a project evolve over time. “If they can both get my point more clearly, and feel more inspired and excited, that's awesome,” Richardson says. “I would say the inverse is true, too, for me.”

Better than text

Late Checkout is well known among tech companies for its work on community-based products. But the agency owes part of that reputation to its willingness to experiment with the latest technologies, from Web3 to AI.

Spending time on the cutting-edge—and helping others explore how things such as decentralization or machine learning might benefit them—is one of the things Richardson loves most about his job. He gets to try lots of new things, and work closely with senior leaders on ambitious new projects (most of which he can’t talk about for now).

Presenting this work to clients is another area where Capture has helped. One of Late Checkout’s most popular offerings is a 30-day design sprint that takes companies from concept to product in a matter of weeks. Ideally, Richardson would deliver the work live. But with such a short timeline, it’s not always possible to wait until busy founders or executives are available to meet. An async video is the next best thing, and lets Richardson explain the process far better than he ever could via text. 

“That's very much something that you want to do with a video,” he says. “The more that you can emote—the more energy [and] tone that you can bring to express the narrative—the better when you're selling something like [a] brand, which is subjective and requires energy in order to really get on board.”

With written documents or communication, Richardson worries about losing the subtleties of the points he’s trying to convey. But with Capture, he says, “I know that my point will be made X percent better than it is via text.”

Since reporting this story, Theo Richardson has accepted an offer to work at Dropbox.