What It’s Like to Be a First-Time CIO

Editor’s Note: Jason Scott joined Innovation Ads, a full-service online advertising agency, as its first-ever CIO on September 7, 2007. Scott, 31, had never held the CIO role before. Most recently, he ran IT for Corporate Express Imaging, a $450 million division of office products supplier Corporate Express. Scott started out as an administrative assistant in the IT department at Corporate Express Imaging when he was 20 and still in college. Over 10 years, he climbed the corporate ladder at Corporate Express only to realize that he’d have to leave the company if wanted to become a CIO.

Day One: Locked Doors, Missed Connections

I showed up for my first day of work at my new office in downtown Manhattan at 7:30 in the morning carrying a box filled with family photos, framed college degrees, certificates, awards and code samples. I reported for duty wearing jeans and a Pink Floyd T-shirt. Not exactly how I envisioned my first day as a CIO, but I had arrived in New York late the night before with my wife, two kids, dog, cat and luggage, and I simply didn’t have time to unpack my power suit.

The Innovation Ads office was previously used as the set for the fictional Mode magazine office featured on the sitcom Ugly Betty. I stepped off the elevator on the 21st floor, but the door to the hip, brightly colored office was locked. I was the first one there, and since I didn’t have a key, I couldn’t get in. A few minutes later, a stylishly dressed employee showed up. I introduced myself to him as the new CIO and asked him if we could get into the office. He pulled a credit card from his wallet, slid it between the door jam and the bolt, and opened the door. Note to self, I thought, Improve security on office doors.

I located my sleek corner office, put my stuff down and went to find my boss, Iain Grae, the president and cofounder of Innovation Ads . He wasn’t in his office so I tried calling him. No answer. I later learned that he was in Europe.

Iain and I first met and became good friends when we were students at Florida Atlantic University in the late 1990s. In 2005, he offered me the CIO job at Innovation Ads, but my career at Corporate Express was going very well, and a move to New York simply wasn’t feasible for me at the time. (I was living and working in Florida.) Iain and I stayed in touch, and two years later he asked me again to join Innovation Ads. The timing was much better for me and my family. I had just finished a big project at Corporate Express and was ready for a change. And Innovation Ads was in a much stronger position when Iain approached me in 2007.

I wandered back to my office and just sat there, not quite sure of what to do. I knew I was expected to be a contributing member of the team on day one. Yet I had no specific direction. Was there something I should be doing on that first day? Were we in the middle of a project? It was definitely a little disconcerting and very different from my previous experience at Corporate Express. Each time I moved into a new position there, I spent the first week moving into my new office, getting my stuff together and meeting new staff. I could ease into it. But here there was no ramp-up time. The first day I walked in, it was as the CIO.

By 9 o’clock the five members of the IT staff started showing up. They stared at me through the windows surrounding my office as if I were a fish in an aquarium, and I peered back at them with uncertainty. After 15 minutes I said to myself, This is ridiculous, and I went out and introduced myself to them. I told them about my background and about my extensive programming experience. They looked at me like I was full of it. In essence, they told me: “Everyone who comes in here tells us they know systems and development.” I asked them about their jobs and about the company. I was just trying to get the lay of the land.

It was an interesting first day, for sure. I felt like a boxer who had survived round one against a world heavyweight champion: I didn’t win. I didn’t knock down the champ, but I didn’t lose or get knocked out either. I was relieved I got through day one without any major issues.

Next: Facing Down Loneliness, Fear, Frustration and Self-Doubt

Facing Down Loneliness, Fear, Frustration and Self-Doubt

My first week on the job was frustrating. I didn’t know any of the staff. I didn’t know any of the vendors. I didn’t know the interactive marketing industry or its terminology.

At Corporate Express, when someone talked about delivery problems or FIFO and LIFO costing, I could speak that language. At Innovation Ads, everyone was talking about campaigns, enrollment management and lead generation. I didn’t know what they were talking about. People were giving me projects, saying, “We need this client to be able to do a co-reg, but they’re also driving an affiliate network.” I was scribbling down notes but I had no idea what they were asking me to do. That was scary.

There were times when I wondered, Oh my god, what if I make things worse? What if I can’t do this job? I imagined the core system crashing for five days and the company losing $10 million. What would I do? I didn’t know who my go-to people were. I didn’t know if my staff was going to accomplish what I needed them to accomplish.

In my previous role, I had a lot of people I could ask for advice. I had known them for a decade, and they were always happy to talk things out with me. Here, I had no one to ask. I had to rely on myself and do what I thought was right.

Getting the Lay of the Land, Finding a (Temporary) Go-To Person

Innovation Ads was so different from Corporate Express.

For starters, Innovation Ads, which launched in 2002, is privately owned. It’s driven by speed, progress and growth, while Corporate Express, as a public company, is burdened with compliance, regulations, reporting and controls. I always thought that when I became CIO—wherever that was—that it would be very formal and hierarchical, much like it was at Corporate Express, where you have to have “gray hair” to be promoted to executive management and where every executive has a front-row space in the parking lot. At Innovation Ads, everyone on staff is my age or younger. There’s a music studio in the office for employees. It’s a substantially different environment and not what I expected, though I must say it’s certainly no less effective or lucrative than Corporate Express.

I tried to adapt to my new environment, and I resolved to do my best. I came in early. I worked late. I read up on open-source technologies such as Apache, PHP and MySQL, since they were new to me. I also started reading books, news articles and white papers on online advertising, e-mail marketing and behavioral targeting.

Six Tips for Surviving Your First Ever CIO Job

1. Expect the unexpected.

2. Identify your go-to people. Seek out one or two members of the IT staff whom you can ask for advice and approach with questions about the company as you get up to speed.

3. Don’t rely on your go-tos too much.

4. Trust your instincts, judgment and experience.

5. Read up on your new company, industry and any and all unfamiliar technologies your company is using.

6. Solve some small, visible problems within your first few weeks on the job to help build some momentum.

–M. Levinson

To get my arms around my new position and employer, I found someone on the IT staff to be my go-to person. Whenever I got a task, I talked it over with him. I asked him what he would do and what the company had done in the past. I selected my go-to guy on the basis of his tenure. Out of the five people on the IT staff when I joined, he had been at the company the longest—a year.

Relying on my go-to guy was a double-edged sword. Not knowing him very well, I didn’t know if he was really any good. I also found myself becoming dependent on him over the first couple of weeks—especially as other developers, who had tired of being pulled in different directions by my predecessor, started leaving.

Then our most important system went down. Two weeks into my tenure, our core online advertising engine, iPMS, which tracks campaign activity and success rates and transmits leads to and from clients and vendors, stopped working. The application wasn’t receiving leads into its database, so lead forms that customers were submitting weren’t making their way into the system.

In our business, leads are our lifeblood. They’re our product. So when iPMS stopped working, the sales team rightly started freaking out and raising hell. The sales director stormed into my office and asked, “Are we having a problem with the system?” I had no idea so I asked my development group what was going on. They ran some queries and tests and told me exactly what the sales director told me, “Looks like no data is being inserted into the database,” they said.

I sat down and started looking through the code with them. Using pure systems logic, I quickly identified the problem. A lower-level developer had changed a core configuration file by accident during testing, and that change directed the application to a nonexistent database server—hence the reason why lead forms weren’t entering our system. Within minutes, we fixed the problem, and just like that, we were back in business.

That was a big moment. Fixing a mission-critical problem engaged me with the business. It’s a funny thing: I started in the CIO role with grand visions of how I was going to change the world, and yet it was this one minor system blip, which lasted at most five minutes, that was the catalyst that helped me build my confidence and that gave the company confidence in me. Go figure.

Things went South again a week later: My go-to guy gave his notice. I panicked. What now? I thought. I’m going to have a completely new staff who doesn’t know the system and neither do I.

My go-to guy’s quitting turned out to be a blessing in disguise: It took away my crutch and forced me to walk on my own. I had to lead the charge. Things started getting better, and I quickly learned the system—trial by fire, so to speak. I felt more powerful and far less dependent.

Next: Hiring Right, Rallying the Team

Hiring Right, Rallying the Team

When I first started at Innovation Ads, there was a distinct lack of team spirit among the IT staff, primarily due to their long-standing frustrations with the prior technology leadership. People showed up at nine, parked themselves in their cubes, put on their headphones, worked on their projects and left at six. No one talked to each other, or knew what the others were working on. Nor did they care.

The first thing I did was weed out people who didn’t share my enthusiasm for programming. I live for software development and application design. I simply couldn’t do anything else. If I won the lottery tomorrow, I’d be sitting at home writing computer applications. It’s what I love. Anyway, I hired six new developers, and everyone who came on board wound up being really good. This is the team that’s going to take our company to the next level.

Hiring is hands-down the most important thing for a CIO, for any manager. If you can’t build a good team and hire the right people, you will drown—no ifs, ands or buts about it. Few CIOs have the time anymore to step in and solve technical problems themselves. My days are full morning to night with vendors, management, shareholders and staff. Even if I wanted to step in and do this stuff myself, there’s simply not enough time in the day.

Finding the right people that you can count on—and letting them know how important they are—is key. I told my development group that they’re the crown jewel of the company, and that the company could win because of them alone. I told them that they were my number-one priority—that my own boss came second. “What’s important is what you guys need from me,” I said. “My boss has five direct reports he can call on. You guys only have one boss.” I let them know that I was going to represent them to upper management and that I would take full responsibility for any technical problems that came up. I wanted to shield them from politics and blame and bolster their faith in me as their leader.

When I worked for Corporate Express, I was driven to work hard not because I really cared for the company (how excited can one get about office products?) but because of my boss, the national vice president of sales, Al Zoldos. I learned a lot from him every day I was there, and I trusted and respected him. All of his direct reports did. I truly wanted to make him proud.

At Innovation Ads, I decided that I wasn’t going to try to sell my developers on working hard for the sake of the company. That’s a cliché. I wanted to get them to work hard for me, the way I was inspired to work hard for Al. And in exchange, I do everything in my power for them. If they believe that I truly care about them, which I do, I have a much better chance of getting them to help me and thus, help the company.

One thing I did was purchase new computers for my developers with 90 inches of monitor space. You could fit a full-grown New York Knick’s guard on the monitor. Everyone in the company took notice of the technology team’s giant new machines. It made my group feel special, and I think it helped inspire them to do their best work.

I also created wallpaper for their desktops that featured the Google logo in a rifle’s cross hairs and put it on all the developers’ machines. Google is by far our largest competitor, and I wanted to align my developers around a common foe and make it clear to them that we’re shooting for the top. We are not out to be a successful online marketing company; we are out to be THE successful online marketing company. I want Innovation Ads to be as well known for its advertising platforms as Google, Microsoft and Yahoo.

When everyone else in the company saw the wallpaper, they wanted it on their machines, too. Between the monitors and the wallpaper, the technology group’s zeitgeist had begun.

What a Difference Six Months Makes

Over the course of my 10-year career with Corporate Express, I became a go-to person. I felt like a star, but at the same time I always wondered in the back of my mind if my star status was due to tenure or talent. I took this job with Innovation Ads for many reasons. First, I always wanted to be a CIO. Second, it was a great company in a new and exciting industry, and I relished the chance to help it achieve its true potential. Finally, I wanted to test myself—to see if I could replicate my success at Corporate Express in a new position, with a new company, in a new industry, in a new state with people I’d never met before—and more importantly, with people who had never met me.

Although the first couple of weeks were tough, I’m now six months into my job and I have to say I am loving life. This is what I want to do. This is where I want to do it. This is what I worked a decade for. This is my dream.

The executives and managers who’ve been with Innovation Ads from the start are running an extremely successful business. What they’ve done here is amazing, building a company from zero to the multimillion dollar company it is today. They might not have one single gray hair, and their style is definitely more freewheeling than stodgy, but they’re just as effective, productive and successful as the rest of corporate America, if not more so. I’ve learned a whole lot more about management and motivation here than I would have had I worked another 10 years at Corporate Express.

I’m getting way more satisfaction and joy now building and guiding a team than I got from being the go-to guy at Corporate Express. I’m watching my team grow, make the right moves and be productive. I’ve doubled the development staff to 12. Productivity has grown tremendously. The accuracy of code has also gone up tremendously. Instead of having to light a fire under my staff, I have to hold them back. They’re smiling, laughing, arguing and doing all the things a team should. The whole company’s morale is up because of the development group. I sometimes sit in my office watching them work and I smile with pride.

And yes, in case you were wondering, the doors to the office are now secure. They lock and unlock via electronic security cards. We know who comes and goes at any time, and we can even unlock the doors via the Internet if we have to.