from fashion to social work: the Jill Wood story
I founded Headmistress, my fashion accessories brand, in late 2008 from the ground up — it began with zero sales, no website and nary a social media follower. I was fresh out of University, yet ran every aspect of the business from product concept, creative direction, design and production, to PR, brand building, marketing, ecommerce, as well as retail, wholesale and tradeshow sales.
I grew the brand into a living, breathing business that I’m so proud of - people who aren’t even my mom actually bought my pieces. I started on a whim, fresh out of university while living in London (England, not the one in Ontario). After just a few weeks, I had myself a full-time business. Along the way, I celebrated major wins - selling to big retailers like Anthroplogie, Indigo/Chapters, Simons and The National Gallery UK, as well as dozens of boutiques across North America and Japan. I was accepted into the insanely exclusive Toronto and Chicago editions of the Christmas One of a Kind Show, and I partnered with brands like Smirnoff, Pimms, Bud Light and Batiste Dry Shampoo for exclusive experiential event activations. I managed to find a niche and develop a viable business for my proudly Canadian-made brand - I created beautiful pieces and convinced people to buy them, or put another way - essentially I made a living by building and maintaining relationships. My interest in people and their stories endures, and I intend to build on this skill set in a different way through social work study.
In January of 2018, after much thought, consideration and a whole lot of reflection, I decided to close Headmistress. It was a decision that I didn’t take lightly, as Headmistress had been an integral part of my identity and life for pretty much all of my post-university life. I knew that I needed to make room in my head and my heart for my next adventure.
I plan to take the skills I developed through Headmistress and apply them to a career pivot into social work. I’ve always been interested in people and relationships - how people interact with one another and how each individual’s circumstances and experience can shape their actions and motivations. I believe that the combination of my past entrepreneurial work experience, my McGill sociology degree, volunteer experience and genuine curiosity about people and the world have prepared me well for my next chapter.