As a bookish, shy, and geeky child of the 80s and 90s I think a lot of it was the right place and time. I was drawn to computers from an early age perhaps because they were both rare and magical things, but also common enough to have one in the home by my pre-teens. I remember being desperate to mess with any and all computers through my childhood - both the opportunity to play video games but also the chance to just tinker with them and try to understand the underlying systems and hardware.
Then, as a lonely teenager in a small town in Atlantic Canada, having the run of the house computer and access to the internet made my life bearable. Messing around on the internet, excitedly downloading each new version of Netscape Navigator, or hanging out on IRC and Geocities was how I spent many many hours.
So I knew I wanted to do something with computers, but there was far more luck than intention in my early path into this career. By the end of highschool I’d made friends with other people who were also very into the possibilities and idealism of the internet. The group had a great mix of complementary skills on design, technical, and entrepreneurial fronts, understood the web better than the average person at the time, and had excellent early support from parents. We brashly started our own business, perfectly timed to the first commercial internet boom, and it all built from there.
I’ve been a few things over my career - I started as a developer and then slowly grew into a technical project manager and eventually my current role as CEO of silverorange. I’m not sure I have an actual area of expertise - I was always a good and improving developer and at the same time surrounded by people far better than me. Which is a pattern I try to continue in all parts of my life.
Growing up, I never saw myself as a leader in anything - and once we began silverorange it took me more than a decade to start to ease into any position of authority on a project let alone a team. I was a decent project manager and ended up in the role because no one else really wanted to do it, and that was the pathway into realizing I both liked and had a way with the complex systems that are teams of people working together. When silverorange’s first CEO decided to move on, I realized I had built up the varied skill set that was needed to take over the role, and was ready for a new type of challenge.
Thankfully my partners and co-workers agreed, and it’s now been more than five years of honing the variety of skills I need in that role. Which is just a start. I don’t have to do any of it alone - I’m surrounded by a strong leadership team who split the responsibility and work with me. The way I interpret my role I end up helping in all things - business development, financial planning, team development and hiring, client relationship work, being a problem-solving sounding board, occasional project management support, and even very occasional programming all happen. I miss programming. Although really - I should be kept away from most code at this point.
In the last few years, we’ve successfully grown from a very long term and stable team of around a dozen, to a team of twenty-one. For the most part we’ve done this while keeping what we feel makes us a special and successful organization in place, while also gaining the huge benefits of new people and their skill sets and backgrounds. We are far less a monoculture, have reached gender parity or better in most levels and roles within the company, and our team culture is better for it. It has been matched with increased financial success as well.
The ongoing challenge of this is how we continue to push forward in who we want to be as an organization. For a very long time a team of 20 seemed a terrifyingly large number of people, and now we’re on the way to 25. And I’m starting to see how we could grow past that. This is not fast growth by startup standards but is for us - and we want to be sure we continue to adapt to the changing needs of a team at this scale without losing the core of what silverorange is. Inevitably this will require new skills and approaches to how the company works, but I believe we can navigate that while continuing to serve our core tenants of meaningful work, ethical existence in the world, and serving the needs of the people that make up our team.
Currently this means we’re busy figuring out how to manage a larger team while not being a bureaucracy, how to change our corporate structure to accelerate employee ownership, and thinking about how we can create opportunities for more underrepresented groups in our industry. It’s been a long time since I’ve believed that the work we do for our clients is all that matters and we can just be apolitical as an organization - it is ever more clear with each passing year that the choices we make affect the world around us.
I want to continue to focus on silverorange as a platform for improving the lives and opportunities of the people at silverorange, as well as an advocate for our industry doing the work of improving at large.
It’s a lot easier to list technologies I’m concerned about, which says a lot to me about the lack of a deep ethical framework for our profession.
That said on a personal level I’m excited by the new Apple Silicon MacBooks. I just upgraded to one, and my early personal review is that it’s one of those subtle but momentous shifts in everyday performance. Not dissimilar to when I got my first computer with an SSD and then tried to use a machine with a spinning disk again. Plus all day battery life and no fan! I’ve long been nerdily excited about improvements in processing power, and this is the first time in a long time that I’ve felt that old feeling of excitement at a new computer.
Professionally, I’ve been part of many transitions in tools and technology stack for web development, and each one has brought exciting new benefits and corresponding tradeoffs.
I like that we have built our business in Atlantic Canada. Over the years we have done a lot of work with venture capital backed businesses in multiple waves of speculation, and I think being based out of Charlottetown has helped us have perspective and stay true to our desire to build a business that was a platform for the lives of the people working for it, instead of getting too caught up in chasing the money, or trying to be a unicorn startup. That’s a path many want, and I know some very smart and excellent people who have taken it successfully without being corrupted. However it’s not a version of success I was or am interested in, and I have a lot of pride in the work, business, internal culture, and team that silverorange has built over the last 21 years.
Over the years, outside our busy agency lives, we have tried to build a couple of software products of our own and had them fizzle out. I think everyone in silverorange would clearly see our own responsibility in those failures, and at the same time I’m sure we’d have had more opportunities to be successful in those ventures if we had been in San Francisco or a similar tech hub. I get the impression that this lack of access is not as big a struggle as it was 10-15 years ago.
And being based out of the east coast of Canada never prevented us from working with a lot of interesting big and small clients from any part of North America - it has often been a point of novelty but never a detriment in any way.
At this point, almost half of our team is not in the Atlantic region, and most of our business has always been from outside the region - so semi-regular travel to get people together or to visit our clients can be a challenge. But people do love coming to PEI in the summer, so that helps.
I love learning but I’ve never been the most self-motivated person. I’m not someone who teaches themselves new programming languages or professional skills in their personal time. So the way I’ve always found motivation to learn new things is to throw myself into groups or projects that require developing those skills, and then learning by doing in a peer environment.
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