Jennifer Jackson

The Path to Pineapple Street

The Path to Pineapple Street

Jenny Jackson ’01 was no stranger to publishing when her book, Pineapple Street, made its debut in March 2023. She has spent most of her career working behind the scenes as an editor in trade books, rising from an editorial assistant at Vintage to her current position as vice president and executive editor of Alfred A. Knopf. At the beginning of the Covid-19 pandemic lockdown, she began writing her first novel. A fictionalized look into an ultra-wealthy New York family, Pineapple Street became an instant bestseller and has a TV adaptation in the works. We spoke with Jackson about her life as a student at Williams and how it led to her career as both an editor and a writer.

When you started at Williams, did you know you were going to be an English major?

Not really. My freshman year, I did, I think, exactly what you’re supposed to do: I dabbled around. I took Psych 101, geology, an English class that specialized in poetry—a little bit of everything to see what I liked. Late sophomore year, I took a step back and thought, “Well, I just keep signing up for English classes. So maybe this tells me something.” It came about very organically, even though in hindsight, it seems like, how did I not know this is what I would do?

Did you have an idea of what you wanted to do after Williams?

No. I didn’t even figure it out until I’d been out of school for a year. While I was at Williams, I was soaking it all up like a sponge, but I wasn’t thinking a lot about what was next. I was really in the moment. And then I graduated, and I took a job at a not-for-profit that I found interesting—but it was clarifying, because I was like, oh, no, I really, really want to be working with books.

I didn’t know very much about book publishing—I didn’t know the different kinds of jobs you could have, and I didn’t know anybody who worked in book publishing. Then I learned about the Columbia Publishing Course, which set me on the track for an editorial assistant job pretty quickly.

How did Williams prepare you for a career in editing?

So much of what I did at Williams lined me up for that first job in publishing. I had taken a class in what was then called Latina and Latino fiction, and we studied Sandra Cisneros, Esmerelda Santiago, Julia Alvarez and all these amazing writers. Now I’m publishing Esmeralda Santiago as her editor, and we’ve published Sandra Cisneros at Knopf. I’ve interacted with many of those writers, which is just incredible.

I took so many poetry classes, especially with Larry Raab [the Harry C. Payne Professor of Poetry, Emeritus], and he and I have kept in touch over the years. Louise Glück was at Williams while I was there; she was just a knock-out professor. I had professors who were really open to working with me. I also had a great group of friends who were supportive of my writing. I’m mortified when I remember going out to dinner with some friends when I was at Williams and making them listen to me read poetry at a restaurant. So embarrassing.

While I was taking the Columbia Publishing Course, Jenny Minton [Quigley] ’93, who was an editor at Vintage, came and spoke. Afterward, I went up to her and said, “I think I went to Williams with your sister [Katie Aisner ’99]. She and I ended up having a great, friendly conversation. A month later, she posted a job. I went in for the interview, and she hired me. I never would have gone up and chatted like that if it weren’t for the Eph connection. And I’m unwilling to contemplate how much our Eph connection actually got me the job. [Laughs]

Vintage was the paperback arm of the Knopf group, and back then, the Vintage editors were basically the backup readers for the hardcover editors. Every week, the hardcover editors would send down the manuscripts they were interested in pursuing—to get backup reads on. I was reading five novels a week and writing three-paragraph reports [for each]. The huge volume of reading was potentially overwhelming. I had to digest 100,000 words, be able to summarize it quickly and have an opinion on it.

I still think, 20 years later, that’s a pretty sophisticated piece of work. That English degree straight-up teaches you how to do that. Especially those survey courses. I did my senior seminar on the works of Jane Austen and George Eliot, and we read a lot of really long books. Just being able to plow through it and digest and metabolize it is a huge skill set that has stayed relevant.

I have such gratitude and fondness for my education and for Williams. I hope that at some point, I can come up there and maybe pay it forward to some students.

Were there other experiences from Williams that influenced your book?

I definitely felt like I encountered [socioeconomic] class in a different way when I arrived at Williams. That was something that surprised me at the time and informed the way I think about it.

I love that [Williams has] done away with the work-study component of financial aid. It always seemed unfair to me that some students had to work campus jobs while other students didn’t. It set up a divide that everyone was aware of.

What advice do you have for English majors or would-be authors?

As a book editor at a trade publishing house, I have the stereotypical publishing job, but there is a whole world of subsidiary rights, book clubs, agenting, book-to-film scouting—there are tons and tons of jobs that people don’t know about that they can apply to and find a foothold in. When people only apply for editorial assistant positions, they’re really limiting themselves. Cast a wide net through the industry, and think about ways that your passions can intersect with different parts of publishing. There are more avenues in than people might imagine.


More interviews with Jackson:

The New York Times



ABC’s Good Morning America


Regina Velázquez is an assistant editor and senior writer in the Office of Communications.