Deirdre Findlay, Chief Marketing Officer of Stitch Fix
Deirdre Findlay
CMO Stitch Fix Logo

How Stitch Fix CMO Deirdre Findlay Blends Art and Science for Career Success

For Stitch Fix CMO Deirdre Findlay, striking a balance between both creative and analytical thinking helped drive her to a successful career in marketing, which included stops along the way at eBay and Google. When it comes down to it, she says, it really is about trusting your gut. Below, read on to see how Deirdre applies that mindset to her leadership style as well.

Tell us about what you are doing now.

I’m the Chief Marketing Officer at Stitch Fix, the world’s leading online personal styling service. We’re experts at both data science and human empathy, and I get to harness both of these to grow and develop our brand. We debuted our first fully integrated brand campaign during awards season that’s all about feeling “red carpet confident” each day, and celebrating life’s everyday moments. I’m really proud of the campaign and love being part of a company that embraces people for their uniqueness. Outside of the office, I’m at SoulCycle or Barry’s any chance I get; my day is much more productive when it starts in the studio!

How did you get to where you are today? 

It all started with my parents, who are both Jamaican immigrants. They raised me to believe that I could do anything in life with a good education and good old-fashioned hard work. I went to a liberal arts college (Williams) and majored in Economics, which turned out to be the exact balance that I needed – both creative and analytical. I learned that I thrive in environments where I’m using both sides of my brain. It was my experience at Dartmouth’s Tuck School of Business that ultimately led me to marketing. My internship at Pepsi exposed me to marketing strategy, and I knew I’d found my calling. I took my MBA to the global marketing and technology agency, Digitas, where I spent 11 years helping businesses transform for the digital age. I wanted to be a CMO, so heading to Silicon Valley to build and scale marketing for digital-first brands felt like the natural next step. This is what I did for eBay, Google, and am now doing at Stitch Fix.

What do you see as the major opportunities and challenges for women today?

"Without mentors and advocates, we’ll never make positive change."

While there are more and more women in the workplace, I believe the insights, approach and leadership skills we bring to the table are still too often overlooked. I feel strongly that ALL leaders need to be held accountable for ensuring women have the opportunity to be heard and rise to positions of power and influence. Without mentors and advocates, we’ll never make positive change. I think it’s also important that women feel brave enough to show up in a way that’s authentic to them, and don’t try to embody someone else’s idea of what leadership is. It’s something I’m constantly challenging myself to do as a leader, and supporting my team through.

One of the reasons I joined Stitch Fix was because of the company's commitment to seeing, listening to, valuing people from all different backgrounds, and with different perspectives. This is true internally with our employees and with our clients, and it’s a key message in our first brand campaign.

What solutions or advice can you share?

Trust your gut. Before business school, I spent three years in reinsurance, where I really enjoyed the numbers but felt like something was missing – the right-brained, creative thinking element that I love. I knew this industry wasn’t for me, and also felt in my gut that business school was the best next step to find out what was [for me]. Despite friends telling me I needed at least five years of work experience to get an MBA, I applied, was accepted, and found my career in marketing that I’ve never looked back from. Another bit of advice I give is to be purposeful about the roles and projects you seek, to set yourself up for future success. On my path to CMO, I considered the skills I would need to secure that role, and went after them.

Who helped you in your journey, and what advice did they give you that really shaped your thinking?

"These stretch opportunities helped me go from a “doer” to a leader, with confidence."

I’ve been lucky to have so many different sources of inspiration along my journey. One of my first mentors at General Reinsurance, Sue Johnson, showed me what a strong female leader looked like. She navigated a male-dominated industry with seeming ease and created room for other female leaders to rise under her leadership. Her “trust your instincts” advice gave me the courage to attend business school despite having only three years of experience. Tony Weisman, former CEO of Digitas North America, also made an impact on my career. After a long tenure a Digitas, I began to feel like I was in a box and that my growth was being stifled as a result. Tony saw my potential and cared enough to create opportunities for me to lead. These stretch opportunities helped me go from a “doer” to a leader, with confidence. Tony taught me to ask for what you want, don’t wait for it to come to you.

What one thing would you have done differently early in your career if you had the right bit of advice?

Something I would do differently is to leave the agency a few years earlier when I started to get comfortable. We learn the most when we’re operating at the edge of discomfort, and every role I’ve taken moving forward has had elements that pushed me out of my comfort zone alongside others I excelled in. Getting out of your comfort zone is the best way to keep learning!

If you weren’t doing what you’re doing now and money or talent would be no object, what would you be doing?

I think I’d either try my luck as a golf pro or embrace a personal passion and become a real estate and interior design guru. Finding the perfect properties with great potential to redesign, decorate, and transform into beautiful homes would satisfy my need to use both the right and left sides of my brain – and maybe it would land me a vacation house, too.