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What’s it really like to work at Chicago startups and tech companies? Blue Sky’s Inside Job lets people on the ground tell us in their own words.

Kevin Lester, 29, Trading Analyst at The Trade Desk

So the short story is we help agencies that represent advertisers buy ad space online and on TV. That’s kind of the most general approach. The longer approach is we help those agencies with advertisers know how much to pay for an ad and more importantly, know who they should be targeting.

Before, it was target everyone and hope people who are interested see your ad. It’s like my getting ads for tampons in Spanish. I’m in Chicago, English-speaking and I’m never going to be interested in buying tampons unless they’re for my wife. It’s a useless message to me, whereas that ad can be spent better on someone who’s relevant to that product. That’s what our tech does.

I work in a team of three: There’s a business executive, an account manager and then a trader. My role as a trader is to implement the campaign. I’m looking at the campaign running in real time. So I can see, of the people we’re showing ads to, who’s clicking on these ads? Who’s watching the videos? Who’s actually buying the product? And then in real time, I start targeting the campaign toward those people.

Because ad tech is such a new industry, and it’s ever-evolving, we’re constantly serving as trainers. We teach clients how to use the platform. The best-case scenario would be, I start out a campaign, and through instruction, by the next campaign, the clients are able to do it. That’s really the only way we’ve been able to scale so quickly as a company.

We just crossed over 40 people in the Chicago office. We have 20 offices worldwide. Our headquarters is in Ventura, Calif. With total employees, we’re at about 600. We were founded in 2009 and then IPO’d in 2016. I joined the company last October.

I grew up in Idaho, near Boise, on a farm. My wife, her name is Meredith, I took her to the Minnesota State Fair this Labor Day, and we spent like four hours in the dairy barn because I did all that stuff growing up. I went from an Idaho farm to New York City for college and then settled in the Midwest.

I got recruited to wrestle at Columbia University — I love New York. I went to school for one year, and I took two years off (for a Mormon mission) in the Dominican Republic. One place we were in was literally the jungle, and there were two months where we didn’t have electricity. The biggest part I took away from it was being able to teach anyone and make everything applicable to them and their circumstances. That’s something that’s really helped me professionally.

After I graduated in 2012, I moved to Chicago. I worked for Meadowhawk Capital. I was on the floor at the S&P options. It was a great environment. It was super-competitive. I went to a bigger company, TMG, TransMarket Group, for two years. Then, the product I was trading, Eurodollar options, they decided not to trade anymore.

I was searching for finance stuff, and I figured The Trade Desk must be finance-related. And then I was like, “Wait, this isn’t finance. It’s ad tech.” I went down a LinkedIn rabbit hole, and I contacted someone at Vivid Seats, and he had a floor-trading background like me, and he said, “If you’re really interested in finding something similar to finance but is more creative and in the advertising industry, look at The Trade Desk,” and he actually hooked me up with a recruiter, and that was how the process started.

The biggest concern of our leadership is, “We’ve gotta preserve our culture as we scale.” A big part of it is every year, we have a thing called Palooza. It’s been on the West Coast. Every employee in every office gets flown in. We go for a week, and it’s conferences during the day. All the traders break out. All the C-Suite speaks. At night, there are dinners. We have a comedian come in. The last day, we have live-band karaoke. Anyone can sing, but there’s no teleprompter, and you have to rehearse with the band. I was blown away by how good a lot of people were.

For our summer party, our Chicago office went to Arlington (Park). Everyone dressed up, like for the Kentucky Derby. It was catered, open bar, all of that. Los Pinguinos, our company softball team, is a big deal. The joke was that I got hired to be on the team. I’m first base. We won the championship this year.

There’s this excitement in how fast the company is growing but also in the industry and how much impact they could have in it. This industry has only been around for a few years. Who knows where it’s going to be in five years? So you can have a direct impact on what it looks like.

My manager and I have weekly one-on-ones. I tell him, “My clients have been having success with this. I think other clients would as well.” Within three weeks, it could be a product that everyone in the company has, so it’s very quick. There’s satisfaction in seeing that.

There’s a few things in the platform that I could point to and say, “Those were suggestions I had, and now we’re using them.” It wasn’t like a two-year process. It didn’t have to get passed off to someone else who pitched it as their idea.

As told to freelance reporter Erin Chan Ding. Stories are edited for length and clarity.

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