March 5, 2019

Lead(H)er: Amy Jacobowitz, Head of Content at Getaway

When Amy Jacobowitz lived in Los Angeles, she found herself taking small vacations to the desert every other month. There, she could rest and recharge before heading back into the hustle and bustle of the big city.

“I needed that escape and to be somewhere new while doing nothing, and I didn’t realize how rejuvenating it was when I was doing it,” she said.

Now a New Yorker, Jacobowitz works as the head of content at Getaway, a startup that rents out tiny cabins in lush, woodsy settings two hours away from major cities to let people experience that same refreshing break.

It’s a perfect match in more ways than one. After a career beginning in public relations, Jacobowitz strategically moved herself towards content and now oversees all of the content related to Getaway’s brand voice. That includes the company’s website, social media, journal, brand partnerships, and events, among other responsibilities.

Jacobowitz majored in history during her undergraduate years and expected to go to graduate school after, but a shaky economy led her to take a job with an advertising PR agency with which she had interned during her senior year. When one of the founders of that company split off to create a new agency, Jacobowitz followed.

“I think the benefit of working in the world of advertising is that it has some of the most creatively-minded people and smartest people who are really trying to tackle things strategically,” she said. “It got me into a different mindset.”

At the same time, Jacobowitz entered and won a branded-content screenwriting competition. The experience showed her that she enjoyed writing within specific parameters, and she soon began putting that talent to work at Funkhaus, a creative agency that designed websites, named and branded companies, and wrote content—such as email newsletters and blog posts—for clients.

In public relations, it’s often difficult to promise clients that they’ll see a return on their investment, as so much of the work involves sending pitches that may not be acted upon. Being able to commit to delivering work and following through on that commitment felt more rewarding, Jacobowitz said.

After four years at Funkhaus, Jacobowitz began to wonder what she could accomplish if she dedicated all of her energy to a single brand, instead of multiple clients—and if she could do it in New York City.

“I applied to 200, maybe 250 jobs,” Jacobowitz said. “This is not an exaggeration. It was like a full-time job, and it was relentless.”

Realizing the importance of having a zip code closer to the opportunities she wanted, Jacobowitz moved to Brooklyn. Shortly after securing her new zipcode, she landed a job at coliving startup Common.

Now at Getaway, Jacobowitz heads up a team as scrappy and determined as she’s been throughout her career.

“I love the concept of idea agnosticism that we have here,” she said. “If you have a great idea and can get people really excited about it, it doesn’t have to be routed through levels of approval. As long as it feels on brand and it’s a good idea, it can happen.”

The company is continuing to expand, with plans to establish a collection of it signature tiny cabins in the Atlanta and Los Angeles areas this year, and Jacobowitz is happy to add to her full slate of tasks to support the growth.

“I think Atlanta is an example of a place that people might not consider when they think of a place in need of a break from a chaotic city, but it’s still very much in need of an escape,” she said. “I love the idea of trying to expose Getaway to people that might seem traditionally underserved by traditional notions of self care. Something that’s really important for me and my happiness at work is to be constantly moving the needle for a company that I think is on the right side of history.”

Rapid Fire Questions

What do you like to do in your free time?

We do a really good job of breaking between work and leisure time at Getaway. We have every first Friday of the month off because we’re moving towards the ideal of a four-day workweek. I spend a lot of that leisure time reading—I’m a true crime fanatic. I also love to cook, hang out with my dog, spend time with my friends and family, and take 35mm photos. I’m a movie buff. I try do some creative writing on the side—probably not enough, but it brings me a lot of happiness.

How do you manage stress?

I go to therapy, which is really helpful with ensuring that I always have a great perspective on my personal and professional life. It helps keep me grounded, and it’s really helpful for me to check in and see if I’m operating at where I want to be. I’m grateful for this job and the work that I get to do and the team we have in place, so remembering that helps me reduce my stress.

How many cups of coffee do you drink in a day?

I have a morning coffee, a coffee right after lunch, and then a tea in the evening. I managed a coffee shop for four years, so I love everything about the ritual of coffee.

What’s one of your favorite places in the NYC area?

I love my neighborhood of Brooklyn Heights. It’s so cozy and wonderful, but I also love getting away to Hudson, which is just upstate. It’s an amazing small town with incredible food and culture—just the perfect small community. It’s a nice break from shoving your way through the streets of New York.

What do you consider one of your greatest accomplishments so far?

I think moving to New York, the struggle of finding a job here, and physically reorienting my life was so huge. To be able to do that and also do well in that new job is something that I try to pat myself on the back for.

The other thing is the way I’ve been able to mentor people that are interested in content. I've been able to help interns that I’ve worked with get hired at a few of the places that I've worked, and that's such a great feeling. I’ve enjoyed getting them inspired and excited and passionate about content and helping them unearth what their passions are and how that intersects with the working world, their goals, and the company goals. That’s hugely rewarding for me.

Is this where you saw yourself 10 years ago?

I think 10 years ago, I saw myself as a screenwriter. I lived in L.A., and that was everything that was around me. This is quite different than that, but also there's a lot of overlap. You're still writing to parameters and structure and thinking about your audience all the time. So I think that there's some overlap, it’s just that the platforms are so very different. I think the 10-years-ago me would still be happy that I'm making a living off of my writing.

What’s your advice for recent college graduates?

I would say that while your hard skills are super important, your soft skills are just as important. Practicing communication, being kind to people in the workplace, being a real active listener, and being observant about when it’s the right time to listen and the right time to speak up makes people want to work with you, and it helps them remember you. All of the networking that has been organic and not forced has really been critical to my own success. It’s something that’s often overlooked, but I can’t understate the value of just being a good person to work with.

Samantha Costanzo Carleton is a Contributor to VentureFizz. You can follow her on Twitter @smcstnz.