How indie devs at Smile won 100,000 happy customers

How indie devs at Smile won 100,000 happy customers


Greg Scown, CEO of Smile
Smile CEO Greg Scown leads the team that created popular Mac apps TextExpander and PDFpen.
Photo courtesy Smile

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Smile, the indie development team behind super-popular productivity apps TextExpander and PDFpen, cut its teeth writing software for technology that barely exists anymore. But thanks to a user-focused attitude and a wholehearted embrace of the third-party tools that power modern offices, the company has been able to keep ahead of the curve as technology changes.

“Smile has its roots in fax and disc-labeling software, neither of which are particularly relevant today,” Greg Scown, CEO of Smile, told Cult of Mac. “Both were productivity software designed to help users save time on everyday tasks. That’s really the heart of what we do, and it has enabled us to evolve to create and promote new products over the course of our lifetime as a business.”

Smile and the art of the pivot

Just as Apple started out as an underdog computer company but went supernova with the iPhone, Smile’s savvy pivot from barebones fax software to a powerful PDF editor and beyond illustrates how paying attention to customers’ needs can pay off, big time. For Smile, that translates into 100,000 users of the company’s software for Mac, iOS and Windows.

Having been around since since the days of discs and fax machines means Smile has seen the nature of work evolve just as radically as the software it sells. From the advent of email to the rise of co-working spaces, companies more than five years old have been forced to decide how to adapt, which tools to keep and which to leave out.

The last 15 years brought rapid change to the workplace, and Smile has been a consistent early adopter of the productivity tools that empower modern teams.

“I like to say we’ve been a virtual company for at least a year longer than it was practical to do so, and this means we use lots of online tools,” Scown says. “Slack has proven to be a very helpful and effective team communication tool. We also use FaceTime and Skype a lot.”

Solving the challenges of app creation

Smile team
Separated by many miles, the Smile team collaborates using tools like FaceTime and Slack.
Photos courtesy Smile

Those tools come in handy for a team of more than a dozen workers scattered around the globe trying to achieve common goals. To handle other crucial tasks, Smile turns to code repository GitHub, web applications integration service Zapier and social media wrangler Hootsuite, he said.

The DIY approach isn’t without pitfalls. App licensing turned out to be a particularly tough nut to crack, especially since the company’s most popular software, TextExpander, is no longer sold through Apple’s Mac App Store. (Smile removed its powerful cross-platform app, which saves keystrokes and lets team share snippets of text and code, due to a change Apple made to Mac security.)

Some of Smile’s software can be purchased from the Mac App Store, but TextExpander and others get sold directly to consumers. Still, until recently, Smile lacked a solid platform for licensing its apps — and for making sure the licenses were being used appropriately.

“In the activation realm, we were basically on the honor system,” Scown says.

That turned out not to be a great thing. Through a usage survey, Smile discovered that organizations comprised of hundreds or even thousands of users were using licenses meant for five or fewer people. Smile knew it had to implement a structured licensing system to ensure fair use of its products, but that’s no small task. Building a licensing platform in-house means spending loads of time and money developing a feature that doesn’t actually improve the product, at least from a user’s perspective.

Third-party platforms can be an indie dev’s best friend

Rather than committing a team to developing an authentication system from scratch, Smile simply implemented a ready-made third-party platform. For the many developers in Smile’s situation — looking to improve a key area of their operation without dedicating time and resources to a massive new development project — going with a such a third-party platform is a no-brainer.

Smile picked DevMate, an app development and distribution platform from MacPaw. The transition was “pretty painless,” Scown says. “In a way, this is the activation system that we would’ve liked to build had we decided to build it ourselves. And we are very grateful for not having to build it ourselves.”

The switch also gave Smile fresh insights. The company is obsessed with data-driven decision-making and was surprised to learn, for example, that more than 90 percent of its user base updates to the latest operating system within three months of its release. Now that vital information gets presented automatically in easy-to-understand graphs and visualizations.

“All of a sudden, we went from having the ability to answer sort of one-off queries to having a graphical presentation of the same type of data we’d been collecting all along,” Scown says. “It brought the same data into a much more useable form…. We could just look at a dashboard and there it was.”

Fresh perspectives are a welcome bonus

Going with a third-party solution solved a known problem (the pain point of app licensing) as well as an unidentified problem (a lack of insight into user behavior).

The happy end result in this case is that Smile gains time, and valuable knowledge, to do what it does best — focus on crafting software that solves users’ problems.

“Everything is challenging in the app business,” says Scown. “That’s what makes it interesting to do. It’s tough to keep one’s products fresh and relevant. It’s not easy to reach new customers. It can be difficult to keep up with Apple’s pace of evolving macOS and iOS. It’s fun to juggle all of these challenges with the end goal always being to help our customers get their work done.”


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