2023 Distinguished Alumna encourages students to give themselves grace about big decisions

Holly Sears Sullivan ’90, Harpeth Hall’s 2023 Distinguished Alumna Award winner, believes firmly in making mistakes.

“We put so much pressure on ourselves to make the exact best decision every time we have a decision to make,” she told students, “but very rarely is a decision a one-way door. Often, it’s an opportunity.”

Decision making and quick thinking are essential to Ms. Sullivan’s work as the vice president of worldwide economic development for Amazon. Her path to this role has been full of big choices, unexpected detours, mistakes, and risks — themes she touched on throughout her interview.

Ms. Sullivan graduated from the University of Tennessee with a bachelor’s degree in urban studies and master’s degree in urban and regional planning. Harpeth Hall seniors Julia Allos and Annie Linley interviewed her on stage during an all-school assembly about her career journey, what a day in the life of an Amazon leader looks like, and what lessons from Harpeth Hall she still uses today. They began by asking what advice Ms. Sullivan would give herself as a student.

“Be patient, listen a lot, and build a bench,” she said.

By “bench,” Ms. Sullivan explained, she meant a group of mentors and friends who can provide support both in and out of the workplace, especially when the path forward seems uncertain.

“Having those people who believe in you makes it easier to get up in the morning and do it all again,” she said.

Ms. Sullivan’s interest in built environments began with her parents, who worked in real estate. While taking college courses on business finance and calculus, Ms. Sullivan realized she didn’t want to go to business or law school. Instead, it was a class on economic development that intrigued her.

“I was always interested in the things around me,” she said. “Why is that road there? Why is that building there? I wanted to find out.”

This class built on that early interest and spurred her to forgo law school to pursue her passion, despite the risk of judgment.

“The thing Harpeth Hall did for me — and it’s such a gift — is it gave me confidence. The confidence to take the path that not everyone’s taking. The confidence to trust my ability to make the right decision,” Ms. Sullivan said.

With this leap, she began her illustrious career in urban planning. One opportunity led to another, and she soon worked her way up to serving as the president and CEO of an economic development firm in Rockville, Maryland.

“I’m a big believer in saying yes,” she said. “When someone opens a door for you, go through it.”

Drawing from questions submitted by students in advance of the assembly, Annie asked how Ms. Sullivan ended up at Amazon. Ms. Sullivan shared a story of her time at an economic development firm in Washington D.C. Despite leading the company successfully as their number one, she was told she would be better suited as the number two — with a “middle-aged man” presented to her as the more apt person to lead.

“I went home and cried. I thought, do I pivot to something else? Do I accept being number two? Do I get out and focus on raising my child?” Ms. Sullivan said. “The next morning I woke up with a new lens. All I did was change my profile on LinkedIn to indicate I was open to a new position. Amazon called me one hour later.”

At Amazon, Ms. Sullivan’s work focuses on land acquisition, site scouting, and collaborations with local governments. In 2018, she led the search for a second headquarters for the company, a search that spanned more than 200 cities. The result of that search, which led to Amazon opening its Operations Center of Excellence in Nashville and creating 5,000 jobs, is one of her most notable career successes. But, that is not all she does. To put her job in more relatable terms, Ms. Sullivan asked students about a pop culture favorite, a teen movie.

“How many of you have watched ‘The Summer I Turned Pretty?’” she asked, to which a majority of students raised their hands. She explained that part of her work entails working with state governments to scout locations and obtain permits for filming.

“Understanding the power of land use and land rights is so important,” Ms. Sullivan emphasized. “We ask questions like, ‘How can we scout locations and consider traffic so that we won’t be as much of a bother?’”

As the interview wrapped up, Julia asked what success meant to Ms. Sullivan.

“I’m not always the perfect mom. I’m not always the perfect business woman. I’m not always the perfect wife. Some days I’m just mediocre. Success to me means making peace with that and taking care of my mind and my body.”

She encouraged students to give themselves grace about big decisions, as failure is often the best teacher.

“Sometimes you just have to rip the Band-Aid off and decide,” she said.