Cathy Polinsky Sets Engineers Up For Success at Stitch Fix

With an emphasis on onboarding and new-hire empowerment, seasoned CTO Cathy Polinsky gives everyone on her team a voice.

Cathy Polinsky is part of an elite club.

Women hold just 20 percent of C-level roles at U.S. companies—but Polinsky, the chief technology officer at Stitch Fix, is doing her part to make that club less exclusive.

These obstacles have been ever present during Polinsky's long career, but they haven't stopped her from pursuing the work she's loved since the first grade. After majoring in computer science at Swarthmore College, Polinsky graduated at the peak of the dot-com boom and went straight to work at Amazon. Since then, she's worked at a startup, served as an engineer at Oracle, become an engineering manager at Yahoo, and led an engineering team at Salesforce through sky-high growth. For the past 18 months, she's worked at Stitch Fix, a subscription clothing company led by a female CEO.

"When I started at Stitch Fix, our engineering team was just over 30 percent women, and now we're at 35 percent. Female leaders attract women to the organization, because when women see other women at a company, they realize that it's a place where they can be supported," Polinsky says. Below, she shares the challenges she's overcome to reach the C-suite, and how she's helping others to do the same.

To me, mentorship includes an entire support network of peers, former bosses, and colleagues.

— Cathy Polinsky, chief technology officer, Stitchfix

MSF Hub: When did you know you wanted to pursue a career in technology?

Polinsky: As a first grader: I went to a school computer lab once a week at a time when most people didn't have computers in their homes. I started doing Logo programming with these little "turtles" that made shapes, and then graduated to doing basic programming. I loved the problem-solving aspect of it.

The summer after my junior year in high school, I attended a camp at Carnegie Mellon University for computer science. Mornings began with algorithms and various computational problems, and in the afternoons we did special projects around robotics or programming. I loved it. I got a lot of encouragement from the professor there to pursue it as a course of study.

MSF Hub: What were some challenges that you faced when you were starting out?

Polinsky: The biggest challenge of my career was early on when I was an engineering manager at Yahoo. I'd had my first baby and come back to work, but the way that I was working before just wasn't right anymore. I wasn't doing a good job at home or at work. So I quit. As I was getting ready to leave, an executive came to me and said, "Cathy, you're not asking for what you want. I don't know if we can give you what you want or need, but you're not even giving us the chance. The worst that can happen is we say no."

I was taken aback. I changed my work schedule and my child-care situation. It was a critical point for me because I realized that when things are challenging, a conversation with one person can make a difference.

MSF Hub: How important has mentorship been throughout your career?

Polinksy: To me, mentorship includes an entire support network of peers, former bosses, and colleagues. If I'm having a challenging day, you'll most likely see me walking the halls and looking for people who may have a spare moment to talk through a challenge with me. The key is to seek the right person for the problem that's in front of you.

MSF Hub: The lack of women in tech, especially engineering, is not a new issue. But things haven't changed significantly. Is there a solution?

Polinsky: Early on in my career, I was brought into a big cross-functional initiative with leaders from multiple departments. During a meeting, I realized I was the only woman in a 50-person room. That feeling can be scary, which is why we have to help the next generation get to a critical mass of women in the field.

When I was at Salesforce, CEO Marc Benioff was a huge supporter of women, and challenged his executive team to have 30 percent female representation at all of his leadership meetings. There's a notion that at a critical mass, people no longer feel like they're underrepresented, which means they have influence. We have to strive for that.

MSF Hub: How do you empower, inspire, and train the women you work with today?

Polinsky: At Stitch Fix, we talk about issues that many other organizations find hard to address. We talk about unconscious bias and how we can be supportive in the interview process to ensure that we're getting a diverse candidate pool. We think about our onboarding process and offer an immersion program for all new hires. We give them a buddy to help them understand the Stitch Fix culture and set them up for long-term success.

MSF Hub: Is it working?

Polinsky: We hire people from different companies and backgrounds, and some of them carry baggage with painful experiences that they've had in the past, whether that has had to do with gender bias, discrimination, or other personal challenges. When we train and onboard employees, we try to create a safe environment where people can be vulnerable in talking about how we'll all work together to create a culture where everyone thrives. We teach people to speak up for each other, be advocates for themselves, and strive for continuous improvement for everybody around them.

Maria Minsker
By Maria Minsker | June 08, 2018