Shawn Holmes: A B̶r̶i̶e̶f̶ History

I'm the CTO of Wrapmate, lover of all things tech, gamer, 80's fan, pop culture enthusiast, curator of an extensive digital music collection, and pun aficionado. The only thing I love more than building cool technology is building great teams to do so.

The Geek

I am a naturalized US citizen, born in Melfort, Saskatchewan, then raised on Vancouver Island, British Columbia, in a town named Parksville. If you suspect you knew me growing up, but the name doesn't match, it's because I took my Mother's maiden name in 1990; prior to that, my last name was Zurba.

My life changed on Christmas morning, 1982: a Coleco Vision arrived under the tree. For the next thirteen years, I spent every waking moment doing whatever I could to get my hands on video games. I played Donkey Kong and Zaxxon until I could wrap the game, blindfolded. I needed more.

The next major event came in 1985 when the Elementary school I attended received its first personal computer: a single Apple II Plus. Every student in Grade 5 was put on a rotation to get a turn with it during lunch hour. This led me to make deals with kids who didn't care about computers, usurping their time and diving deeply into programming. I was 11.

By 1995, I owned an NES, Super NES, Sega Master System, Sega Genesis + Sega CD-ROM, Turbo-Grafx 16, 3DO, and even the fabled Neo Geo which played my most prized game: Samurai Shodown II. By this time I was already disassembling some of my favorite PC games to see what made them tick, experimenting with hex editors, changing values, seeing what was possible. I also began dabbling in the C programming language.

My love of Samurai Shodown II drove me to write a FAQ, drawing the attention of Dave "Zoid" Kirsch, who requested it be hosted on his Brawl FTP server. This introduction led to a friendship and Zoid encouraged me to pursue computers and the internet in a professional capacity.

I taught myself HTML while doing technical support for a local Internet provider. I learned as most did, circa 1995: "view source", editing in Notepad, uploading via FTP, testing in Netscape. A chance meeting with a person in the rec.arts.disney Usenet group selling a movie on VHS led me to make a risky bet: in December of '95, I crossed the border and married my true love, Julie. Unsurprisingly, we have two young video gamers as a result: Ariel (24) and Hunter (23). Julie & I recently celebrated our 25th wedding anniversary.

The Developer

The World Wide Web underpins my career trajectory. It began in 1997 doing HTML development for Colorado SuperNET. No Visual Studio Code, no debuggers. I bounced back and forth between Eclipse and FrontPage '97, which led to a side-gig: teaching HTML at a local community college.

From there, I went to work for Research Systems in Boulder CO, as "Webmaster." Don't let the title mislead you -- it was glorified web development, with one key difference: it was my first opportunity to build dynamic web applications (complete with database!). My language of choice: ColdFusion.

By 1999, the dot-com era was bursting at the seams. I took a gig in Omaha, NE for 5 months, which ended up being a wash – as with many companies at the time, they were flush with cash but lacked a business plan. I returned to Denver the same year and took on a position as Senior ColdFusion Developer with Breckenridge Communications, a family-run agency. This was a five year stint. I learned a ton, expanded my network of colleagues & resources, worked with many companies across multiple verticals, and was my first real taste of agency life.

From there, I moved to Creation Chamber, where the real agency life kicked into full gear. For the next six years, I led development projects across even more verticals, touching some major brands like the Denver Broncos, Einstein Bros. Bagels, Denver Public Schools, Brother's BBQ, and more. Nearly all of my energy was focused solely in Content Management System development & implementation, and this is where I grew both my development skills and my customer relationship acumen.

Time and again, I was called to ensure the customer was satisfied and required me to interact with them constantly (rather than through a sales associate proxy). It was these six years in agency life that forced me to be extraordinarily efficient in process. At the start, rolling out a single CMS implementation took several weeks; by my exit in 2008, multiple implementations would roll out in parallel, daily.

The Lead

After a decade of agency work, it was time to move into a more corporate setting. In 2008 I took a Senior Development position with Kaniza Media, a division of PER (Physicians Education Resource). This team, located in the DTC, was focused on building CME (Continuing Medical Education) learning systems for Oncologists.

By now, I'd developed strong opinions on The Right Way™ to build software. I'd spent the better part of a decade cleaning up after other developers' decisions -- it was time for me to make a mess and build my own system from scratch. The next three years were fantastic: I was a member of a small, tight-knit group of rockstars all working closely together, building a robust LMS. We rolled our first version out a few weeks after the launch of Stack Overflow.

Kaniza would be the first time in my career a mentor would step forward and plant the seeds of something greater in my back of my mind. You shouldn't be developing...you should be leading development teams.

Kaniza came to end (sadly) in 2011, so I took several years of healthcare-domain knowledge with me to DaVita, the renal care company featured in John Oliver's takedown of the Kidney Dialysis industry.

Fun fact: I was able to land the position at DaVita through a former colleague that remembered my work from Breckenridge Communications - he even showed me that my code (written back in 2002) was still operating a key system to this day! This was both exciting and disturbing, due to what I perceived was the apparent lack of investment in healthcare IT.

DaVita was a unique experience. Although hired as a Senior Developer, I was very quickly promoted to a position of pseudo-manager, picking my own consultants to hire, direct, develop & maintain projects. I likely wrote only a few lines of code in the first month or two, but spent the next 4 years documenting specifications, working with business owners, coordinating projects and ensuring their delivery. At times, it almost felt like I was more focused on bridge building than on actual software delivery, smoothing out the friction between the many teams demanding IT's assistance and our ability to provide solutions and ease their collective pain.

I was architecting entire end-to-end solutions, encapsulating the complete SDLC, and given the authority to select & run the teams necessary to execute their development. The only thing missing from the picture was the actual Manager-IC relationship; nobody reported to me, I wrote no reviews, and I wasn't responsible for anyone's budget, bonuses, hiring or firing.

That changed in May of 2014.

The Manager

Thanks to the support and encouragement of several mentors, I successfully made the leap from individual contributor to development manager in the spring of 2014. Reporting up through the Director of Marketing Services for Truven Health Analytics, I inherited a team that were responsible for the development & maintenance of both the corporate website as well as several legacy internal apps.

For the next five years, I was not only responsible for the success of these sites & apps, I was responsible for the careers of the development team that reported to me. I instituted 1-on-1s, built career paths for each team member, ensured they received adequate training, and celebrated our deliveries with team outings, further cementing my determination to foster a positive software development culture.

And now, with my foot in the leadership door, I gained my first exposure to the upper echelon of corporate: the directors, the VPs, and sometimes even those in the C-Suite. With finesse & diplomacy, I could have their ear, gain sign-off / approval of major initiatives, and affect the success of the departments that relied on mine. It forced me to tear down & rebuild my entire suite of communication skills. Increasingly, it became important to be able to speak to my audience, build alliances across department, and then cash that social capital in when I needed it to move mountains. The big picture became much bigger, more political, and required more strategic thinking.

It was no longer about me or the software. It was about the people.

The Director

Truven Health Analytics was purchased by IBM Watson Health. I was lucky enough to get a short time behind the Big Blue curtain and experience once of the most established (and most bureaucratic) technical behemoths in the history of American capitalism...yet I yearned for more. Instead of moving mountains, I wanted to be the mountain others might seek to move. The next logical step was to manage the managers, get a seat at the big boys (and girls) table, and help make strategic decisions that would lead to a company's greater success.

With the help of a long time mentor, I was able to make this next leap by taking on the role of Director of Software Development at ████████, a division of ████████ ███. This was a challenge unlike one I had ever faced before.

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Three months after he hired me, the VP of engineering left the company. ████ ███████ █████████ █████ █████ ██ ███  ██████ ███████████ █████ Trello, ███ ████████ ████ █████  ██████████ █ ███ ███ ███ █████ ██ ████████████ ███████ █████ Slack, opting instead to  use Microsoft Teams, ██ █████  █████ ███████████ ████ ██████ █████ ██████ ███████ ████ ██ risk management ██████ ██ █ ███ █████ ██ ███ ███ ████ ██████ ██ ████ ████████ ██████ ████████ ████ ██████ █████████ ███ ██████ ██████ ██████ ████ █████ ████████████ Christmas █ ███ ██████.

By January, I ████ ██████ ████████ ███████████ █████ ███. █████ ███████ █████████ ███████ █████████ ████████████ ████ ███████████ ███ ███. █ ██████ Cincinnati ██████ █████████ ███████ ███████ ███████████ ████ ███████ ███ ████. When COVID-19 struck, ███ █████████ ███ █████████ ██████ ████████ ██████ █████████ ████ ██████ █ ██████ ██ █████ ██ New York ████████ ██ █████ ████████ █████ ████ █████████ █████ █████ ███ █████ ██████ ███████ "Set-up-to-Fail Syndrome" by Jean-Francois Manzoni & Jean-Louis Barsoux. It was a fascinating read ████ █████ ██ ██ █████████ ████████████ ██████████ ███████████ █████ ████ ███████ ███████████████ ██████ █████████████ ██ █████████ ██████ ███.

The CTO

And now we come full circle. Thanks to a connection from a colleague dating back to the early Breckenridge Communications days, I had the great pleasure of meeting Chris and hearing his exciting vision for a tech company that will revolutionize an industry ripe for improvement: vehicle customization. Chris and the rest of the leadership team have some big things planned, so stay tuned to this space for more! I can't wait to share it with you.

Find me on Mastodon (if Twitter dies).