Sean Stephens: CEO & Founder of PerfectlySoft, Inc.

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An entrepreneurial, innovative, and visionary technology leader with a history rooted in computer programming, Sean Stephens is behind Perfect, the first publicly available server-side toolkit for Apple’s open source Swift program¬ming language. He founded PerfectlySoft Inc. in 2015. In addition to PerfectlySoft, Sean is the CEO of two other successful technology startups, LassoSoft Inc., and Treefrog Inc. He also serves in advisory roles for several nonprofit organizations in Canada including The Executive Committee of Canada, Seneca College, Georgian College, and the Employer Leadership Council of York Region.

A dynamic public speaker and pragmatic and analytical problem-solver, his diverse background, technical knowledge, and creativity have seen him earn multiple entrepreneurial and business-related awards. Sean holds a B.A. Honours degree in Political Science, and a B.A. in English from Carleton University in Ottawa.

How did you get into the technology industry?

When I was studying English and political science at university in the early-to-mid 1990s, more than anything else I wanted to be a professional musician. But there was a catch: at the time, all my money was invested in my education, so to fund my musical ambitions I took a part-time job at a computer shop. I started to learn a lot about technology and it whet my appetite to learn more. It was in the early half of that decade that a lot of people were talking about what was then called the information superhighway. I was intrigued by this, and before long, I founded a dot-com using a financial grant from the government I applied for and received.

A few months later, the former owner of the digital marketing agency I now own and run ( called me and proposed we merge our businesses. We did. I soon found myself sitting at a table with my two, new business partners – the owner and a graphic designer. The owner said, “I’m a business guy, I’ll manage the business and sales.” The graphic designer said, “I’m a designer, I’ll take care of our graphic design.” They turned and looked at me. There was an awkward pause, and then I said, “Well, I guess I’ll be the programmer then.”

Any emerging industry trends?

There’s a clear and obvious trend toward mobile technology. Within this trend, there’s a real desire among developers for less fractionalization in programming – fewer tools and languages and skillsets to learn, fewer technologies to support, and easier and more modern tools to use. In other words, programming is changing, and for the better. I heard someone at an iOS developers’ conference in Toronto say, “programming is the new literacy.” I couldn’t agree more. Whereas programming was once considered a “dark art,” it is now becoming accessible to more people because programming languages are getting easier to use, and they’re becoming more human. Therefore, more people are getting involved in programming and are subsequently building quality software and apps. That, in turn, is transforming computer programming from something engineered to something that’s more artistic.

Any industry opportunities or challenges?

The opportunity right now for PerfectlySoft is to take advantage of Apple’s decision to make its Swift programming language open source. Thus, developers can use the Perfect framework with that same beautiful language and do the artistic work that they do on both the frontend and the backend.

The challenge before us is that Swift is a nascent language; it’s still new, and there’s a lot of experienced, older developers who are using Java and Pearl and other languages against which we’re competing. Ergo we’re still trying to get a foothold with developers worldwide. It’s certainly an exciting time and Swift holds much promise for a new way forward, but it’s not definitive yet.

Inspiration for PerfectlySoft, Inc. and your vision for it?

PerfectlySoft owes its genesis to another company called LassoSoft and the Lasso programming language. Many moons ago, the heads of that business were commiserating that the company was well on its way to becoming irrelevant. Out of that conversation, it dawned on me there was an opportunity to leverage Lasso, and create a new company and technology because Apple had stated it would eventually make Swift open source. It was then quite obvious to us that we were a lot farther ahead than we thought. So we put all of the necessary pieces into place and quickly started building Perfect.

What's next for PerfectlySoft, Inc. in the near future?

We’re going to be working closely with major cloud providers to create easy mechanisms for people to deploy their applications, and with the global Swift development community to continue to evolve Perfect and make it as intuitive and compelling as possible. That means attending as many iOS and Mac developers’ conferences as we can to meet Swift developers and introduce them to Perfect and how they can use it to build their applications from front to back faster, using less code, and with fewer bugs.

Your key initiatives for the success of PerfectlySoft, Inc.?

Priority No. 1 is to make the best product we possibly can, and for that product to be truly enterprise-grade, which is to say it is scalable, secure, and powerful. We also need to continue to multiply the number of Perfect tutorials and other on-ramps developers can leverage to use it effectively. Strategic partnerships, too, are a critical ingredient; we’re currently working on solidifying a few partnerships with major industry players.

Your most difficult moment at PerfectlySoft, Inc. (and what did you learn?)

There seems to be a new difficult moment each week. A couple of those moments have caused me ponder whether or not this business is viable. For instance, when a major competitor entered this market I initially thought that was it for PerfectlySoft, but as it turned out, their foray into the server-side Swift arena helped to validate what we are doing, and it helped us to continue to move forward. That particular experience taught me to do what I’ve always done: remain confident in myself and my team, and not make any knee-jerk reactions to any unexpected turn of events.

Ideal experience for a customer/client?

Perfect is free to download and use. Ideally, developers will download it and find it to be a highly useful and easy-to-use server-side framework for their projects which helps them get their products to market faster. In essence, the goal is for developers to realize Perfect can help them do more and better work, and enable their artistic qualities, not their engineering principles.

How do you motivate others?

I beat them until morale improves. No. In fact, I don’t find I need to motivate the people who work here because they’re already highly motivated and they want to contribute, excel, and accomplish new things. We work in an incredibly exciting industry, and PerfectlySoft is at the bleeding edge of server-side Swift development. All I do is provide the right atmosphere and environment for these talented souls to do what they do best. Or maybe it’s my green hair that inspires them.

Career advice to those in your industry?

My advice to any aspiring entrepreneur or developer is to be bold and fail quickly. In my experience, I’ve made the mistake of carrying products my team and I have built well past their best before dates without recognizing that we weren’t heading in the right direction. It’s incredibly tough to let something you’ve put so much effort and energy into go by the wayside. I suppose it’s akin to being a parent in that even when your children grow to become adults, you still can’t help but love them and want to try to help them be successful when you should let them go their way and figure it out on their own. Sometimes, no matter what the result proves to be, you have to step aside and let nature take its course.