It’s no surprise that Jordan Guggenheim has some strong opinions about online dating. He’s an engineering manager at OkCupid, one of the world’s most popular online dating platforms.

“Actually, there’s really no such thing as online dating,” he says. “Eventually you have to meet in person.”

Guggenheim, a graduate of Flatiron School’s New York campus, sees OkCupid as a means to an end, a way to get two people to point where they know enough about each other to get together in real life. And that requires pushing the envelope a bit.

“Historically, OkCupid hasn’t been shy about asking the hard-hitting questions,” he says. But in the past few years, people have shown they care a lot about politics. So we have been asking members questions like, ‘Do you prefer that your date shares your political views?’”

It’s a hot-button topic, but Guggenheim says it reveals a lot about people.

“These simple questions carry a lot of weight in terms of who people choose to date long-term,” he says.

Connecting with a new career

Engineering is Guggenheim’s second career. He started out in finance, a field where he wasn’t satisfied.

“There’s a great saying I live by that goes, ‘Don’t run from something, run towards something,’” says Guggenheim. “I was definitely running from something, applying for other finance jobs and trying to figure out what came next.”

He thought back at his teenage years, when he got a lot of fulfillment out of being creative with online tools like Photoshop. He decided his next career should be in a place where he could combine his love for beautiful design and his interest in technology.

One more thing: He wanted that job to be meaningful.

I wanted to be involved with something that does good for the community,” he says. “I wanted to be able to give back.”

So, in 2015, he started studying software development at Flatiron School. An assignment he got during his second week—working on the interface for a weather app—convinced him that he was in the right place.

“I loved working on the app so much that I was staying up until 1 in the morning,” he says. “I could be very creative, like having the app rain cats and dogs to show that you should bring an umbrella.”

His ingenuity attracted the attention of recruiters from OkCupid. When he graduated from Flatiron School that fall, he immediately started work as an engineer for the company. About 18 months later he was promoted to engineering manager for the iOS team.

Landing in the right place

Guggenheim says he knew immediately that OkCupid was the right fit. He liked the fact that he was part of a “small but mighty” team.

“One remarkable thing is we’re a company of roughly 50 people,” he says. “It’s a very egalitarian culture. We all have a say in things.”

That means the engineering team isn’t just working behind the scenes—it’s helping to make decisions that shape the company. He and his coworkers talk a lot about the advice they give their members.

“We debate a lot, even things like good date ideas,” he says. “It’s great being in a space where you can say, ‘Hey, I went on a good date recently. Let me tell you about it.”

Working at OkCupid, Guggenheim says lots of people ask him for dating advice. He is happy to share his own personal experiences.

“I’d say ultimately my advice is to be open-minded,” he says. “I think we’re so quick to judge, and it takes time to get to know someone. Really take the time to open up and ask the questions that matter.”

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