Digital director, The Hundreds

As the digital director of The Hundreds, Ceilidh (pronounced Kay-lee) MacLeod oversees a team responsible for the streetwear brand’s digital touchpoints—its email newsletters, e-commerce site, digital ads, customer service, and social media accounts—and is responsible for increasing revenue on these platforms. “When I met Ben [Shenassafar] and Bobby [Kim], they knew how to create a community, but needed someone with the skill set to grow the online business,” says MacLeod.

MacLeod was that person, and she gained this expertise through digital advertising jobs at a Vancouver startup she describes as Facebook for realtors, and At both of these companies, she was tasked with quickly acquiring as many customers as possible and realized she was good at it. At, for example, she brought in $15 million in ad revenue.

“Don’t be afraid to put yourself in a room where you’re uncomfortable and around people who aren’t like you.” - Ceilidh MacLeod

MacLeod didn’t plan on getting into the digital marketing space, but she did study business at the University of British Columbia’s Sauder School of Business in Vancouver. Prior to that, she lived in South Africa and remote areas of Scotland before moving to Victoria for high school, where she was introduced to streetwear by her then-boyfriend, who gifted MacLeod her first HLZ BLZ and Tens by The Hundreds T-shirts. “I grew up as a tomboy and wanting to be comfortable, and I remember going to business school and seeing everyone wearing suits and making snarky comments because I was wearing a graphic T-shirt,” says MacLeod. “It fueled me to want to prove to them that I don’t have to wear a suit to be successful.”

Ten months into her job at, her boyfriend was offered a position in Los Angeles and she decided to move with him. It came at a time when she began to reconsider what she did. “It was all about acquiring as many customers as possible. I started to question if I was adding any value to these people’s lives.” When she was hired in 2016 by Ben and Bobby, who she met through mutual friends, she was faced with a completely different scenario. “They were taking their time, and telling stories, and gaining customers organically,” says MacLeod, who runs her own streetwear line called b.Eautiful. “They were feeding a ton of people into the funnel with these amazing stories and these collaborations. But there was leaks here and there.”

MacLeod closed up those leaks by revamping the website, setting up email newsletters, combining The Hundreds’ beloved blog and e-commerce site, and retargeting visitors on Instagram. Her changes have worked. She’s increased revenue on the site by 30 percent and recently launched a mobile app, which now accounts for 23 percent of their sales. MacLeod, who is currently the only woman executive on The Hundreds team, says she doesn’t like to admit gender matters, but she does realize men and women do things differently. Instead of that making her feel out of place, she pushes herself to join the conversations, even if they are male-dominated. 

“It can be intimidating to be the only girl in a room of guys, but we need to merge. We need girls to understand guys and guys to understand girls,” says MacLeod. “Don’t be afraid to put yourself in a room where you’re uncomfortable and around people who aren’t like you.” —Aria Hughes