Company We Keep: Callie Stein

Here, we dive deep into how and why people at Square do what they do. Each interview spotlights one person in a creative role and unearths their inspiration, workday hacks, and career advice. Without further ado…

How would you describe your work to a five-year-old?

I help people work together to tell stories through videos, photos, and websites. I make sure everyone knows what they need to do and when, and solve problems to help make their work easier for them.

What everyday activity inspires your creative work?

I spend a decent amount of my free time catch-and-release fly fishing in the rivers that surround our home in Telluride. The land we fish was once part of a vast swath of land the Southern Ute Tribe lived on since the beginning of time, before they were forcibly placed on reservations.

Fly fishing is an intricate sport. It takes careful study and dedication to understand insect patterns, river flows, and fish behavior. So many things have to go right for a fish to eat your fly and for you to actually get the fish to hand so you can safely release it. When people think of fly fishing, they often think of beautiful long looping casts in calm, open, glassy rivers where a gorgeous (and huge) fish slowly swims up and sips a fly. While there’s a place for that in the sport, fly fishing is often far messier and far more unpredictable. Sometimes you do everything right; you match the hatch, you cast perfectly, your dry fly drifts just right, and nothing. Over and over again. All day. Maybe even all week. Then, the next week you absentmindedly toss your fly out as you’re fiddling with something on your waders and sure enough, out of the shadows appears a gorgeous (and small) brook trout who sips your fly. In a blink you’re looking at the mazes on its back in your net.

Oftentimes I think I wish creative work could be like those big, beautiful loops on a calm, glassy river, but fly fishing reminds me it’s okay to get into the mess.

It’s even okay to have something work or have an “aha!” moment and not know why.

The key is getting back out on the river, in that spreadsheet, or in front of that Figma file, and trying again. Fly fishing inspires me to assess and retry over and over again in my creative work; to try that rock around the bend just one more time because maybe, just maybe, there’s a beautiful brook trout waiting to sip my fly.

What was your path to your current position?

I started out at Square in Account Management, which means I worked with some of Square’s largest businesses and helped them understand how they could better run their business with Square. This meant educating them on products that might be a good fit for them, helping them understand how to run relevant reports for their business, and helping them implement new products or features. I wanted to learn the ins and outs of how businesses functioned with Square; what their pain points were, what they loved about using Square, and what they wished we had in our feature set. I learned how to talk about Square and all of its products in incredibly nuanced ways, memorizing each feature and price, which very much came in handy later. I found myself craving the ability to speak to our sellers on a larger scale and platform.

I taught myself SQL, with a boost from a General Assembly one-day class, so I could make the jump to Square’s Marketing Operations team. My day-to-day role focused on the technical operations of delivering millions of emails to our sellers. We worked with our Creative team that communicates value props, feature launches, and the Square brand and voice. All of the product knowledge I accrued in Account Management allowed me to execute effectively during quality assurance with the team, especially as products constantly updated and changed. After our team migrated our entire email system and all of our creative onto a new software platform, an opportunity opened on the creative side for a creative project manager role. I’ve been a lifelong fan of photography (I shoot film in my free time) and video and already loved working with the team, so I jumped at the opportunity to get closer to the creative side of things. It felt like the right fit for me and a place to apply my previous operations experience to help tighten up the ways we operate and how we ship work.

Who’s your favorite Square seller and why?

I have a sweet spot for Turner’s Kitchen in San Francisco. Turner’s was a weekly (if not more than once a week) stop when I still lived in the Mission in San Francisco. Their caprese sandwich is top notch. The folks there are super friendly and they adapted quickly with Square Online when COVID hit. At Turner’s, you’re always met with a friendly smile and wave, which we all need a little more of right now.

What’s a piece of advice you’d give on getting creative?

Read, read, read! Also, never underestimate the power of talking to people you don’t regularly encounter in your day-to-day work. As we adjust to the nature of distributed work, we don’t have the same hallway chats or lunch tables that naturally facilitated some of those lightbulb moments. Many times when I’ve felt stumped at Square with building new processes, deciding rules of engagement between teams, or reimagining how teams and orgs function, I find reading about how other teams are getting things done helps me think outside of my own initial perception of what’s possible. Additionally, surrounding myself with other Squares and asking for their thoughts usually helps shake things up in my brain so I can see the pieces of the puzzle fall into place.

Square is full of kind, brilliant, and helpful people who are willing to go the extra mile to help their colleagues.

This makes it easy to want to spend time solving problems with them.