Home » Mad Man: A Day in the Life Of Chris Yager, Dir. of Advertising Software Development

Mad Man: A Day in the Life Of Chris Yager, Dir. of Advertising Software Development


Chris Yager, the company’s advertising development leader, came to Dealertrack after working for many years at IBM.

The Vermonter’s transition from a major establishment in the tech sector to an up-and-comer has suited him well, and he’s nimbly filled several roles since joining the company.

One thread runs constant in his experiences here, he tells us, and keeps him going – the promise of working with fantastic teams.

1) How would you describe your role? How has it evolved over your five-year tenure?

I’m responsible for supporting the development teams that build our Advertising and Social products, which include teams in Edison, NJ, Manhattan Beach, CA, and Burlington, VT. I’ve worn a variety of different hats in the past, but they’ve generally focused on building and leading great development teams.

2) What does a typical day in Chris Yager’s shoes look like?

If only there was a typical day! That being said, the Agile cadence does provide some consistent activities, including sprint reviews, release train reviews, and quarterly planning. In addition to those regular activities, there is a constant deluge of meetings on a myriad of topics. As my younger son would say when asked what I do, “Daddy goes to a lot of meetings. Yuck.” I try to explain to him why that’s enjoyable but since it doesn’t involve Minecraft I haven’t quite succeeded. 

3) How do you work towards keeping our customers happy?

My goal is to put our development teams in the best position possible. They are the ones building the amazing products that keep our customers happy. I try and set them up to be as successful as possible, which, in turn, creates happy dealers.

4) What’s the most difficult part of being a Director?

The most challenging aspect is likely dealing with people on a regular basis at every level of the company. I work with GM’s, Vice Presidents, our Leadership team and team members at the individual contributor level pretty much every day.

I need to constantly change my approach and message, to make sure I’m communicating the right thing, to the right person, in an effective way. Combined with the amount of ambiguity that constantly surrounds us, I don’t always hit the mark, but it certainly means the day is never boring.

 5) What led you to start working at Dealertrack?

I was on-call firefighter for six years before coming to Dealertrack. At the time, I was working at home for IBM, so I was able to respond to calls throughout the day.

After 12 years at IBM, I was either going to need to move or travel quite a bit to advance my career, so I began interviewing – I love Vermont and couldn’t imagine moving away from it.

After declining a few offers that didn’t feel like a great fit, I interviewed at Dealer.com. My wife told me “If you don’t take [this] offer, then you should just stop looking.”

It was a great fit – the people, the culture, the work and the talent I was going to get to work with. There have been some rocky points but I’ve learned so much here; I can’t imagine where I’d be now if I didn’t make the change.

6) You’re well known for being the leader of the DMKT Hackathons, along with organizing the regional HackVT co-hosting it. How did you get involved in planning community events?

What seems like a long time ago, Bryan Landerman and I were talking about hackathons and whether or not they would be a fit for us. [Landerman is Dealertrack’s Chief Technology Officer]. Hackathons mean different things to different people, so determining our approach and focus was critical.

For us, it was about creating an event that gave people free reign to explore something they’re passionate about that they may not normally get to explore. This is an incredibly engaging event which has had surprise benefits outside of what we expected. For example, it’s a potent recruiting tool.

Over the years, we’ve gotten great tools from the hack – maps.dealer.ddc [an internal desk-locater tool for finding people in the building] as an example. We’ve been slowly growing the event, bringing it to more sites and with more people, and are looking to continue that evolution.

7) What’s the coolest project you’ve worked on so far?

Financial systems don’t often fall into the “coolest” bucket, but certainly the most challenging project was the first ERP project we started more than four years ago.

Gerry Cincotta, Jeremy Everitt, Jack Mazurkiewicz, Casey Mescher, Luke Dion, Kyle Seymour, Flip Bellizia, Joe Brzoza, and I (plus many others!) spent months in a war room trying to build this new system and integrate it across the board. To say the requirements were changing as we were going is quite the understatement.

It was a rewarding experience, which also highlighted the challenges that come with waterfall software development. I learned a tremendous amount and made some great friends. And no, the rumors of Gerry and I singing Barry Manilow together are in no way true.


8) Do you have a mentor and if so, how has he or she helped you?

There are a few people I regularly consult for advice. One of those is Dr. Sean Collins. A significant portion of what I’ve learned, from a leadership perspective, stems from Sean’s leadership development programs and his sage advice. He’s the type of person that makes the people around him better in dramatic ways. Before you have someone like him in your circle, you don’t know what you’re missing.

The second person I often turn to is Gerry Cincotta. When I look around the wider organization, it’s quite incredible to see the number of people and programs that Gerry has impacted in unique and positive ways. There are a lot of us that turn to him for advice, and I thank him for his willingness to listen and ask excellent questions.

9) What’s something unique about you that team members might not know?

I run an adventure racing organization on the side at www.gmara.org. For more than 10 years, I’ve been putting on 10-12 hour endurance events that are all navigation-based. Teams show up with only an idea of how long they’ll be out in the field and little else. We give them a map and off they go.

The longest race I’ve participated in had my team moving for more than 57 hours straight, although we did take a forty-minute break. They’re some of the best memories you’ll ever make. This summer, I raced with my older son for the first time. At ten years old, he’s the youngest competitor to attempt the event. We managed to finish the entire course with just five minutes to spare.

10) Where do you see your career in 10 years?

We’re evolving and changing so quickly, I have no idea. I do know, however, that I want to have influence and impact. I want to work with a variety of people. This doesn’t give me any clue where I’m going to go or what I’m shooting for, but as long as I’m helping other people be more effective and helping us succeed, I’ll know that’s where I’m supposed to be.