Meet the Developers: Smile Software

Today’s interview is with Jean MacDonald, one of the talented members of the Smile Software team. Smile was founded by Greg Scown and Philip Goward, who both love to write fun and useful software for the Mac and iOS devices.

I’m a long-time user of Smile’s software – in particular the excellent TextExpander. In our interview with Jean, we’ll shed some light on the company, discuss the importance of desktop software in an increasingly web-dominated world, and consider the benefits and drawbacks of developing a single application.

I hope you enjoy the interview!

Tell us a little bit about the Smile team – where are you based, how many of you are there, and what motivates you as a company?

There are three partners — Philip Goward, Jean MacDonald, and Greg Scown — and a number of other people who perform various tasks for Smile. Philip is based in San Francsico. Jean is in Portland, OR. Greg is in Castro Valley, CA.

Other team members are based throughout the US and Canada. We number about a dozen depending on what’s going on at any given time. We’re motivated to ship software to our customers that helps them get their work done faster, better, or easier, and to provide them with fast and friendly support.

It seems like many of the “Smile team” are scattered around the continent. How do you all communicate and collaborate on various projects?

We use email and iChat extensively. Philip, Jean, and Greg meet once a week on an iChat video conference and have been doing so for years.

As a company that has been developing Mac software for almost a decade, what are the main shifts you have seen in the market over the past few years?

The most obvious is the mobile market that first opened up when Apple launched the iPhone App Store. And the iPhone spurred an increase in the market for Mac applications by bringing a lot of new customers to the Mac platform.

The new Mac App Store will also have a profound effect on Mac developers. It’s still to early to tell exactly how the market will change, but we are optimistic that it is a good thing for Mac developers in general.

The Smile Website

The Smile Website

Which aspect of the Mac software industry excites you the most, and equally, which do you find frustrating?

Shipping software to users and improving that software over time really excites us.

Sometimes it’s frustrating when unexpected events delay our plans. Ultimately, we’re really happy with the Mac App Store, but preparing our software took time away from some other things we had hoped to get done faster.

As a developer that exhibits regularly at Macworld, what are the main benefits you see from this conference (and would you recommend it to other developers?)

It’s great chance for us to meet our customers and potential customers. We get excellent in-person feedback on our products. We also get to connect with our friends from other companies, podcasts, and media outlets.

Smile at Macworld, 2011

Smile at Macworld, 2011

Do you feel the need to always be running the latest hardware, or do you prefer to run a simpler setup with fairly basic kit?

Greg used to be the one who bought the newest thing the day it was available, but now he’s running a MacBook Pro from November 2008. Philip and Jean both have brand new MacBook Airs.

Greg has his fingers crossed that he’ll love the new MacBook Pro updates and hopes they’re coming soon. Given that we’re so distributed, having a powerful mobile Mac is critical to us all.

Many Mac development teams focus on a single piece of software. What do you think the benefits/drawbacks are of having a range of different apps?

On the plus side, we can offer complementary products such as PDFpen and TextExpander, and we can offer iOS versions of our Mac software.

On the minus side, we have to be quite careful to give sufficient attention to each product without being distracted by the others.

For someone interested in developing their very first Mac app, where would you recommend they start?

Build your app and ship it. Maybe that sounds trite, but PageSender 1.0 didn’t send or receive faxes via modem. That only came after customers demanded that in addition to emailing from the print dialog PageSender be able to fax via modem.

If you don’t ship to customers, you’ll never get that kind of feedback, and as a practical matter it’s probably better to be selling software while you improve it than to have no income at all.

Do you have any interesting updates in the pipeline that you can give us a sneak peak at?

We avoid discussing future plans in any detail, as they tend to change quickly. We listen to our customers, so there are many features that we add to our products as a result of customer feedback.

Thanks, Jean!

Thanks for taking the time to share your thoughts and experience with us. I really appreciate you taking the time to contribute, and we wish you all the best with the future success of all your apps!


  • sajid ali

    great job! i wana make software through company please give chance me!!

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