The New Job: Chief Technology Officer at Comprehensive Technology Solutions

See the photo above? That’s me, and it was taken at noon yesterday. I’d just come from a presentation with a client, and I think it went pretty well. I don’t think I’ll wear a tie to work every day (I’ll wear a blazer or sport jacket reasonably often), but it’s a nice way to mark the start of my run as Comprehensive Technology Solutions’ CTO.

You read that right: my new job title is “Chief Technology Officer”. If the thought of me being a CTO scares you, you’re not alone. I’m a little worried myself.

It’s a far cry from my last job, and how I got here was an interesting story.

The Evangelist’s Lament

For the longest time — most of the past dozen years — I’ve held the title of “Developer Evangelist”, “Technology Evangelist” or “Platform Evangelist”. The term “evangelist” was coined by Mike Murray, who worked in Apple’s Macintosh division during the Mac’s early days, and it was made popular by Guy Kawasaki. The best way to describe my line of work is probably “platform evangelist”, where the goal is to promote a platform — an operating system, software, service or tool — to technologists who would create new software and services using the platform. For example, in my developer evangelist job at Microsoft, it was my job to ensure that software developers were aware of Windows Phone 7 and had access to information on how to build apps for it. I ran tutorial sessions, wrote articles and documentation, provided example code, introduced developers to each other, provided them with app ideas, and so on — anything it took to get more people to wrote more Windows Phone apps (and yes, given Windows Phone 7 getting into the game a full three years after the first iPhone, it was often an uphill battle).

Being a tech evangelist lets you get up close and personal with the technology you’re evangelizing. At Tucows, I got up close and personal with a big software project that never saw the light of day, but from which I learned a lot of lessons, both in programming as well as project management. At Microsoft, I got to play with their most expensive toys (Visual Studio 2010 Ultimate, which retails for more than $10,000 a licence) and with other tools, frameworks and operating systems (including Windows Phone 7) well before they were available to the general public. At Shopify, I got access to their source code in order to better write documentation, which gave me a window into how top-notch developers write commercial-grade Ruby on Rails software.

Tech evangelists’ number one job isn’t writing software. It’s encouraging, assisting, and promoting development of software on the platform, software or tools they’re promoting. I was generally measured by the software I got other people to make as well as the general activity in the platform ecosystem.

Most of the places where I interviewed didn’t see things that way. By and large, they were startups looking for their first evangelist, and it seemed that their ideal evangelist was a programmer who just happened to be an extrovert. That’s a perfectly sensible thing to do when you’re hiring a programmer, and especially at a startup, where everyone has to be an A-player at what they do. It’s the wrong criteria when looking for an evangelist, a job at which I happen to be an A-player.

The story ended up being the same: I’d be invited for an interview based on my reputation, after which I’d pass the “people skills” litmus tests with flying colours. Then they’d look at my software output, which aside from all the tutorial and example code I’ve written over the past few years, was pretty much nil. I’d been meaning to do some after-work side projects, especially at Microsoft, but I was putting some extra effort into trying to fix a faltering marriage (for what little good it did me), so those had to go by the wayside as well.

“I’ve been an evangelist all that time,” I’d say, “Don’t measure me by my software output; measure me by the software output of the people I evangelized to.

Unfortunately, software output is a very easy yardstick to use. Evangelism effectiveness isn’t. While many organizations have come up with criteria for separating the good developers from the bad, few have any idea of how you tell a good evangelist from a bad one. As a result, this refrain became more and more familiar: “We’re looking for someone a little more technical.”

Well, I thought, at least I’m not as badly off as the guy who got this rejection letter:

This is purported to be a rejection letter from the 1970s. According to Laughing Squid’s blog, a Redditor’s uncle submitted nude photos to various women’s magazines, and this was Playgirl’s response.

As Mobile As It Gets

When I graduated with my computer science degree from Crazy Go Nuts University in 1994, most of the developer jobs seemed to be for banks and insurance companies, and they didn’t interest me. Instead, I opted to join a little upstart interactive multimedia company run by art school grads: Mackerel Interactive Multimedia. It was a different time, an era when CD-ROM drives and sound cards were optional computer accessories, connecting to the internet (if you could get a SL/IP or PPP connection) meant using phone lines and a modem, and Apple was in danger of going under. What we called “multimedia”  — computer programs featuring lively interactions with the user as well as graphics, sound and video — was cutting-edge back then, and I wanted to make it too. Coming from a C and command-line background at school, the transition to the art-heavy, GUI-driven world of multimedia was a venture deep into terra incognita. I remember sometimes getting stuck on some thorny programming problems, but I also remember that I was invariably able to come up with some kind of solution or workaround .

We’re in a similar era again, but instead of multimedia applications on CD-ROM or even floppy disks, we’ve got smartphones and tablets. The iPhone hit the scene only five years ago, and the iPad is a little over two years old. They pack a lot of computing power into a small space, and unlike desktop or laptop computers, they’re bristling with all sorts of sensors (touchscreen, microphone, camera, accelerometer), they can network via either wifi or using mobile data and they’re the computing devices that people keep in their pocket or within arm’s reach most of the time.

The set of Windows Phone 7 prototypes that were under my care back in 2010, charging up.

Mobile tech really interests me, and that’s why I pushed hard to become a Windows Phone Champ when I was at Microsoft. It’s also why I shifted Global Nerdy’s main focus to be mobile. If you Google mobile developer news roundup (without quotes), this blog owns the first page of results; if you shorten the search terms to just mobile developer news, it’s still on the first page of results. I’ve been teaching myself iOS development and plan to do the same for Android; on the off chance that Windows Phone 8 takes off, I’ll have my WP7 skills to fall back on as well.

Once again, I have the same problem: I don’t have a single mobile app in my portfolio. How was I going to get into mobile development?

The Opportunity and the Risk

Creative Commons photo courtesy of

So when my old high school buddy Jesse Singh approached me about being the tech lead for Comprehensive Technology Solutions (CTS), his new mobile development company, I was intrigued. CTS’ first product is SafeMDM, a set of tools that allows enterprises to better manage mobile phones and tablets. MDM — that’s short for mobile device management — is something that interests a lot of businesses, who are feeling the pressure from employees to allow them to use smartphones and tablets, whether their own or company-issued, to get their work done. Businesses are worried that these new devices, which don’t have all the management tools that desktop and laptop computers have, will expose them to all sorts of risk: security breaches, loss of confidential data, breaking regulatory requirements and so on. It’s an interesting problem that organizations are only beginning to think of discussing, and only a small number of development shops are working on solutions.

It’s a big gamble. If I had a family to feed, I probably would’ve said “No thanks.” But at this point in my life, as a (relatively) newly-single guy with no debt and whose biggest expense is a monthly contribution to a retirement savings plan (it’s bigger than my rent), I can take a chance on this sort of opportunity. The job also lets me work from Tampa a third of the time, which lets me maintain my long-distance relationship while I’m there and put in the necessary extra time while I’m here. Freedom-wise, I’m on the same footing as any twentysomething at a startup, so I might as well make the most of it.

Since I’ve always wanted the title, I asked if I could be CTO. Jesse said “yes” immediately. He knows that I’ve been programming since 7th grade, and he knows what I can do.

The title should go a long way toward fixing my apparent “not technical enough” problem.

As CTO, I’ll be leading CTS’ development team, writing specs, reviewing code, doing a little coding myself, researching technologies, schmoozing on behalf of the company, writing docs, writing the blog and doing whatever else it takes to help the company become successful. We’ve got some great connections who’ve already been hard at work lining up meetings with clients, including one where I wore the suit in the photo at the top of this article.

One of my first tasks is to get a small development team up and running. I need developers in the Toronto area who not only have solid skills, but who are also willing to venture into unknown territory and deal with the moving target that is mobile development. If you can develop iOS or Android apps, or if you build back end stuff, I’d like to talk to you — drop me a line at and we’ll talk!

13 replies on “The New Job: Chief Technology Officer at Comprehensive Technology Solutions”

Well congrads on the new “position” I have been following you around for many years its always interesting to read your posts I am sure they will get real interesting with you in management type gig now..

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