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Fashion Career by Day, Podcaster by Night

By Katie Sigeti ’06, philanthropy manager, alumni programs
Alumna Ali Jackson ’05 juggles the fashion industry, dating coaching, podcasting and volleyball.
Lifer Ali Jackson ’05 is a testament to what happens when you embrace the unpredictable. She lives in New York, is a VP at Tory Burch, competes in volleyball and is the founder of Finding Mr. Height, an online dating coaching business and podcast.
While at LJCDS, Ali took advantage of a range of experiences as a scholar, artist and athlete. She wrote for The Palette, competed in Academic League and was involved in theater tech for musicals. She also played volleyball—a passion that was ignited at LJCDS. “Shout out to Coach [Peter] Ogle, who made me fall in love with the game and is the reason I still play competitively,” she says.
Ali attended The Wharton School of the University of Pennsylvania, where she began in The Huntsman Program studying international business before switching majors to marketing and retailing. She was a member of the Wharton Retail Club, which effectively set her on a path toward her current career in the fashion industry.
After graduation, Ali worked for Bloomingdale’s in their buying office for five years followed by stints at Madewell, One Kings Lane and Away. Today, she works for Tory Burch as the Vice President of Planning, E-Commerce North America. “My team is responsible for projecting the sales our e-commerce business will do and ensuring that we have the right products, in the right quantities, at the right time to support those sales,” she says. “We partner with the buying team to determine what products we should have in our assortment and the production team to ensure we have enough of those products (but not too much) and can maximize our profits.”
Outside of work, Ali plays volleyball competitively, and two years ago, she founded a dating coaching business on social media and accompanying weekly podcast called Finding Mr. Height. “My cohost and I just had our first live show in New York City in December 2022 and plan on doing more (and perhaps a tour) in the future. It’s been so much fun and is the creative outlet I never knew I needed.”
Ali credits LJCDS for laying the foundation for her path. “Growing up (which all happened at Country Day, considering I was a lifer), I always thought I wanted to be a teacher. This dream was formed by the incredible teachers I had, from Mrs. Bial in the fourth grade all the way through to Madame Thornton Schilling in high school and many, many more in between. While I didn’t pursue teaching, that love for developing others carried through to my career today. I have also gotten involved in coaching to further my love for teaching—both in volleyball and the little side hustle dating business. I credit Country Day for instilling this in me.”

For the Torreys following in her footsteps, Ali shares, “be open to the unexpected and flexible with your own expectations! I went into my four years at Penn thinking I wanted to be a diplomat or perhaps work in international finance. As it turned out, I hated my international relations classes and was absolutely awful at economics. Staying open to possibilities and being kind to myself that I didn’t need to have it all figured out right away enabled me to find the career I have today—a career I didn’t actually know existed when I stepped onto campus!”


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