Occupation: VP of Marketing at the Times Square Alliance
Location: New York, New York
First job: Selling tickets for a haunted house
Best job: Working at the post office window in my grad school
Greatest Professional Challenge: Figuring out how to produce the best with limited funds
Salary During 20s: Started out at $16k and ended around $36k
Site: timessquarenyc.org

Lori Raimondo, how did you get that f*&%ing awesome job?
I used to work in marketing for Showtime Networks and then MTV Networks. After MTV I took some time off, and I was driving across the country when my former boss emailed me and said, “Would you be interested in this job at the Times Square Alliance?” It actually sounded very interesting, and it was appealing to think of being involved with such an iconic destination.

Was it always your plan to go into marketing?
My undergrad degree was in finance. I’ve always been analytical and logical; I actually went into college as a math major. I worked in finance for about four years, and I like to say I had my midlife crisis early—one day I said, “This is not me, this is not my life, this is not what I want to do.” So I went back to grad school and got an MBA and a Master’s in International Management at Thunderbird School of Global Management, with an emphasis in marketing and advertising.

What are your major responsibilities?
The Times Square Alliance is the business improvement district for Times Square; we provide core neighborhood services, co-coordinate major events, and run the city’s busiest tourism office. I oversee the events that Times Square is involved in, including the New Year’s Eve ball drop, which we produce in partnership with Countdown Entertainment and others. I lend my brain to everything that has to do with New Year’s Eve, from making sure the bills get paid to adding new aspects to the celebration. Good Riddance Day, which takes place a few days before New Year’s Day, where the public is invited to Times Square to discard all their bad memories from the past year, is something I developed. We set up these giant shredders, there’s a mallet to crush things, people line up; it’s cleansing.

What’s a typical December day like for you?
Lots of meetings, lots of press events, and lots of chocolate. Before you’re hired here, if you work for me, you know that you cannot take any time off from the day after Thanksgiving to the New Year. The week after Christmas we have a press event every day. It’s all hands on deck.

How do you spend New Year’s Eve itself?
I’m all over the place. I could be doing anything from giving information to my boss for a press interview he’s doing, to making sure that people’s wishes from our Wishing Wall have made it into the confetti. I walk the crowd checking in on everything and assisting how I can.

The New Year’s Eve celebration is live. Are there elements you especially worry about?
Compared to other live events, such as the Oscars or the Super Bowl, this is an event that absolutely, positively cannot run over. That ball has to drop at midnight. Everything is planned down to the second, and anything that affects that could create a stressful situation.

Who actually drops the ball?
There is a crystal ball on top of a podium located on a stage in the middle of Times Square. When it’s time, the mayor pushes down on a button, which signals the actual New Year’s Eve ball to drop. But there’s somebody in the back room with the computers who actually makes it drop.

Do you have any advice for the people who come out to Times Square to experience the event?
Yes! Dress in layers. Wear wool socks. Don’t make your shoes too tight. Wear a hat. You will meet people from around the globe who have made the trek to this historic annual event, so get to know the people around you and celebrate together.

What kinds of qualities does it take to work on a high-profile live event?
Creative problem solving. Everything is figuring out how to make something happen—whether that’s creating a PR event that’s going to resonate with people or solving issues like adjusting the stage when they change Times Square a little bit and it no longer fits as it used to. New Year’s is an extremely enjoyable event to work on because so much is happening all at once, and your brain is constantly working.