In Conversation with Samantha Ogilvie

Tell us about your background: 

My career path certainly hasn’t been the most linear. I entered university as a theater major and left having pivoted into the study of criminal justice. By my junior year, I had begun to question whether law was the space I really wanted to play in, but I enjoyed it & another pivot so close to graduation seemed unwise. Fashion was something that always appealed to me, having landed my first retail job at 15 and working at Guess (on Newbury Street- very fancy!) throughout college. I thought learning more about the corporate side of fashion might be an interesting way to go, so I focused my energy on obtaining an internship after graduation (and a few months studying Italian in Florence). I was fortunate to find one supporting the wholesale team at Catherine Malandrino and that internship turned into a full-time job in customer service. It was by no means my dream job, but I was thrilled they were paying me to be there. Working for a smaller brand gave me the opportunity to see up close how numerous departments ticked. My position evolved numerous times during my three and a half years there, ultimately to include oversight of customer service, logistics & acting as the in-house contact for our foreign wholesale agents.

Though I was, and still am, grateful for the foundation I built during that time, I found myself becoming a bit antsy and worried that I was hitting a wall where I was. The timing seemed right when a recruiter approached me with a role at Diesel, heading customer service for their Footwear division, which was being brought back in-house after being licensed for a number of years. I took it as an opportunity to learn a new business and jumped. Unfortunately, that move was in 2008, and I was laid off after only eight months. The next two years were a crash course in patience, surrender & resilience. Eventually, after helping friends merchandise their line, some less than thrilling freelance assignments, and a very enjoyable stint as a bridal stylist (Lovely Bride is fantastic and a must visit for any bride-to-be!), I found myself back at Malandrino. I spent another three years there, continuing to learn through numerous changes to that business’ dynamics.

I had garnered the trust of my CEO, and as a result, I took on responsibilities in whatever departments had a need. I learned about retail operations, financial forecasting, licensing partnerships & more. I was also able to utilize our archives to develop a product assortment for our off-price retailers, designed to add cohesion to their excess stock assortments & act as overall margin builders. Once again, my time with this brand, though not without its difficulties, helped to bolster my skills in a number of areas. In the years since leaving a second time, I discovered that logistics means something completely different within the confines of a global PR firm, consulting will alert you to just how well versed you are (or are not) in a discipline, & freelance gigs can be a lifesaver when you are no longer sure where your due north lies.

In January 2020 I picked up on a bit of a whim and relocated from NY to LA. The timing proved to be less than ideal, but I was able to spend time looking inward and assessing what I want my next chapter to look like. I have found the constant through my past professional lives to be an understanding of and appreciation for the importance of operations. I’m now working toward having operations be the foundation of the next bit of road on this path of mine.

What do you wish you’d known when you started out?

You are allowed to change your mind. Early in my career, I found myself seemingly locked into a path that I never actively sought out. When an opportunity in the same arena presented itself, I took it even though (not so deep down) I knew it wasn't the kind of work I really wanted to do. I relegated myself to being on a certain track, and it took me quite a few years to recognize that making a lateral move into another area did not necessarily have to come at a steep cost in terms of seniority & pay scale.

Best career advice you've ever received?

The words “that isn’t my job” should never cross your lips. You end up painting yourself as the opposite of a team player with that one simple phrase. Not only is it a bad look, it could also cost you the opportunity to learn something new.

What leadership qualities are important to you?

I believe in leaders who are keen to share knowledge and contribute to their teams' development and growth. I also find empathy to be crucial in leadership. Acknowledging that your team is made up of actual humans who at times will need support and understanding is so important. Getting to know them both personally (within reason) and professionally can go a long way in fostering mutually beneficial relationships. Recognizing that you can learn from your team as well closes the circle.

What has been the biggest challenge in your career so far? 

I once had a boss tell me that I wasn't cut out to be in sales. It stuck somewhere in the back of my mind, and it wasn't until years later that I realized how much of an impact that comment had on me. I suppose it pushed me to work my way back into sales and prove to myself that he was wrong. Funny enough, that wasn't the challenge. The challenge was recognizing that it wasn't something I actually wanted by the time I was successfully working in sales and garnering feedback that indicated he had been wrong. The challenge was hearing my own voice & not allowing the static of other people's opinions to cause confusion. I don't have that down to perfection yet, but I am working on it.

And for fun, what is your favorite wardrobe staple?

Outerwear- there is nothing that excites me more than finding the perfect topper! Whether it is a studded leather jacket, a grey coat adorned with feathers, a black cashmere blazer, or a classic trench in an unexpected color... I simply cannot get enough.

LinkedIn URL: https://www.linkedin.com/in/samanthaogilvie

Instagram: @sammogilvie