How Stitch Fix is Creating a Technological Flywheel

Episode 48

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How Stitch Fix is Creating a Technological Flywheel

As the CTO of Stitch Fix, Cathy Polinsky is using everything from mobile apps to internal software to completely disrupt the world of online shopping.

“I’m frequently told that I’m unlike any other CTO people have worked with. People seem to be surprised that I’m interested in other parts of the business”— @cathy_polinsky of @stitchfix ‏#ITVisionaries

Show Notes

After years working for companies such as Salesforce, Amazon, and Oracle, Cathy Polinsky (Twitter, LinkedIn) joined Stitch Fix in 2016 and now serves as the CTO.

Since her early days working on her first computer, an Apple 2C, Cathy has loved technology, and it was the technical challenges at Stitch Fix that attracted her to the work. How could she help disrupt the world of online shopping? How could she make a technological flywheel that could feed the company and the customer equally, over and over, getting better and better with each experience? In this episode of IT Visionaries, Cathy talks to Ian about just that, as well as what it means to create a culture that allows employees to do good work and avoid burnout, and her philosophy on what it means to be a CTO today.

Topics discussed: Mobile apps, internal applications, datasets, software engineering, AR, workplace culture, e-commerce, CTOs, CIOs, mentorship.

Introducing Cathy — (1:30)

    • Cathy had her first computer, an Apple 2C, in elementary school. Was always fascinated with math, science, and tech.
    • Growing up, didn’t know anyone in the business or tech industry. Didn’t realize that was a possibility.
    • “Even though I was studying computer science, I didn’t understand what a job in computer science would look like.”
    • An internship led her to finally realize there were interesting problems to solve and jobs to be had that she could love.
    • “The thing I’ve always been most passionate about is getting to solve interesting problems….I love that I get to do that every day and that we’re in an industry that’s changing every day because I always get to learn something new.”

    What is Stitch Fix — (4:00)

    • Stitch Fix is an online personal styling service which disrupts how people are finding and buying things online.
      • It is a data-intensive model and it gets better the more you use it.
    • There is a flywheel of data — the more data Stitch Fix accumulates, the better their service becomes, which leads more people to use it and therefore provide even more data. This allows for Stitch Fix to keep building on a strong relationship with the customer as they continue to use the service.

  • Cathy’s early time at Amazon — (6:15)

    • That was where she learned the growth mindset.
    • Jeff Bezos was always interested in being bigger and not being compared.
    • Cathy grew deeply interested in being in a disruptive space.

  • The technical challenges of Stitch Fix — (6:55)

    • Cathy had to double the size of her team.
    • As CTO, software engineering, IT, product design, product management, and security all fall under her umbrella.
    • Ian: “You are the new hybrid CIO where you’re looking at both sides of the business.”
    • She was just leading engineering at first but after six months she was asked to lead the entire IT organization.
    • There was no consensus that product management was needed, so there was no understanding of what great product management looked like. Now all the teams that don’t have one are begging for project managers.

  • Unique challenges of dealing with internal and external-facing projects — (10:00)

    • The two teams, internal- and external-facing are merged together and there are benefits to having the engineers collaborating.
    • We’re not just building the applications that our customers see or just a mobile app, we’re also building applications for our merchandising team as well. So we build a lot of custom technology for that.”
    • There are applications for their 4,000 stylists, applications that run the fulfillment centers around the U.S., and more internal IT and applications that affect the supply side of the business.

  • How governance works at Stitch Fix— (11:30)

    • At first, the balance was off.
    • The way growth was happening was different.
    • “For the first five years of the company, all the growth was done organically…. So this is a muscle we’ve been building for the company and we’re really just scratching the surface of the opportunity.”

  • What does mobile look like for Stitch Fix? — (13:10)

    • Majority of clients are using mobile, so everything comes from looking through a mobile-first lens.
    • It’s a leap to the mobile app. Most people are more likely to initially sign up not through an IOS app.
    • Style shuffle is a feature that allows users to give a thumbs up or down on things.
      • Started as a hackathon application through Facebook messenger and they realized they had something really useful. They built it into their applications and they are able to connect with more customers and build more data points that allow them to serve customers better.

  • E-commerce and AR — (16:05)

    • E-commerce doesn’t work through AR.
    • The experience of shopping has so many little bits to it that AR cannot replicate.
    • Clients want to use Stitch Fix as a service to discover new things that are perfect for them.

  • Helping to blend tech and the real world — (20:20)

    • “Bringing humans and machines together is what we feel is our secret sauce.”
    • When customers get their clothes and try things on, they provide detailed, rich feedback. That wealth of data is then used to create a better experience next time for that specific client, but it can be aggregated to use for other clients as well.

  • Working with vendors/reducing waste — (22:15)

    • Vendors love the partnership. Stitch Fix provides reports on how the clients are responding to products.
    • Those reports help to reduce waste and create an environment where vendors only need to produce what is actually wanted/needed.
    • It starts at the beginning of the supply chain and accurate forecasting.

  • Breaking the mold of the normal CTO — (24:15)

    • “I’m frequently told that I’m unlike any other CTO people have worked with. People seem to be surprised that I’m interested in other parts of the business.I’m constantly asking questions.”
      • By being inquisitive and keeping an open mind, Cathy feels enabled to make sure she is making the right technology investments that drive value to the business.
    • “The question we’re always asking is, ‘What’s the problem we’re trying to solve?’ …I think my differentiator is coming in and being able to translate business problems into technologies and business opportunities.”

  • Working for and with the employees — (26:05)

    • People matter the most. Investing in employees and making sure they have the best tools is one of Cathy’s highest priorities.
    • If employees have the tools needed to serve clients, the company will be successful.

  • What new tech is Cathy excited about? — (27:05)

    • There is time and freedom to explore new technologies and projects for all employees.
    • There’s been a lot of interest in fit challenges.
      • There is not a good solution to figuring out what are people’s actual sizes.
      • Stitch Fix is investing internally and looking at other technologies to try to find the right solution to this problem.
      • Ask questions about what is particularly tricky for the individual so that a personalized model can be made.
      • Cathy/Ian hot take: “A men’s dress shirt has more points that matter than a woman’s blouse.”
          • Ian: “It’s a great reminder that the answers are all around us every single day. People just accept the status quo for so long and it’s like, maybe there are a few more sizes than just small, medium, large, extra large.”
          • “Data can bare out things we didn’t know or that we always suspected and are actually true.”

  • Getting people to sign up and optimizing that process is a challenge — (31:45)

    • The person is signing up because they want to give up control of a certain experience, and they need to know if they can trust Stitch Fix. So they need to ask the right questions and make sure they take the time to get to know customers in the best way possible.
    • “If a customer tells us something about themselves, we must listen to it. We have to listen to every piece of data they are giving to us, make sure we get it right for them, and not create a mismatch where we’re not giving them what they want.”
    • There’s not one technology where it feels like, we have to do this. It’s about scaling and growing with the company.

  • Listening to employees is critical — (35:50)

    • Stitch Fix an active culture of feedback. There are a lot of employee surveys to get an indication of how the organization is doing with listening and aligning to needs.
    • Every week, Cathy has an all-hands meeting with the entire organization, which includes an “Ask Me Anything.”
    • “It’s all about creating the space and giving people trust that their questions will be listened to and that every question is wanted and acceptable.”

  • Mentorship and how to balance your personal life with your work life — (38:00)

    • Avoiding burnout is so important and is the responsibility of leadership to look out for employees.
    • “It’s about creating a culture for everyone to do their best work and be able to sustain that for a long period of time. If you have everyone running at 110% all the time, at some point they’re going to hit a wall.”
    • Teams need to improve their velocity in a sustainable way so that they can enjoy the work they’re doing while being successful at the same time.
    • Stitch Fix teams sign up for all the work they do themselves and are really bought in and in charge of the whole project they are running.

  • Stories from Salesforce — (39:55)

    • Cathy spent seven years at Salesforce and loved being part of the rapid growth.
    • There was a huge level of investment in engineering managers and a culture of supporting engineers, which Cathy has taken with her.
    • Loved going to Dreamforce and seeing the customers.

  • Lightning Round — (43:50)


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As the CTO of Stitch Fix, Cathy Polinsky is using everything from mobile apps to internal software to completely disrupt the world of online shopping.

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