Daylight Dialogues x Amy Feitelberg

Published on 09/26/ 2020

Amy Feitelberg is currently the Photo Art Direction Lead at Square in San Francisco, CA. She creates the visuals for a forward-thinking company that enables entrepreneurship for all.  Before her leap to tech,  she was the photo director at Los Angeles magazine, and she ran the photo department at Outside magazine in Santa Fe, NM before that. 

She has won several SPD awards including a Gold Medal for best photo essay, as well as awards of Excellence from Communication Arts, and many images published in the American Photography Photo Annual.

Johnny Autry/Square, Inc

Daylight Dialogues: I want to focus on Square’s print publication, The Reader, but can you start with what you do there because I think a lot of people don’t fully understand what photography Square even does.

Amy Feitelberg: My title is Photo Art Direction Lead. I come from an editorial background where I worked at publications like Outside and Los Angeles magazines as a Photo Director for several years. At Square, I work within the studio team that’s part of our larger in-house agency. We work on all the marketing materials across the company. So, we have some of the usual things like shoots for new products that go into our marketing channels, and then we do bigger brand initiatives like storytelling about people who are transforming themselves or their communities with their businesses, and tools at Square are helping them do that.

When I started in 2017, I had just left Los Angeles magazine, and the studio team at Square had just made its first project in what ended up being a series called For Every Kind of Dream. The first story launched was about Yassin Falafel, a Syrian refugee living in Knoxville, Tennessee. With little money or resources, he ended up selling his sandwiches outside the local mosque until he could open a shop. Now he employs other refugees and gives back to his community where he has become a beloved figure and a shining example of the American Dream.

I was so excited to start working at a company that was doing that kind of work and telling those kinds of stories. Square may be the only place I've worked that really walks the walk in terms of what their mission is and what they believe in. So, after Yassin, we continued this kind of storytelling, and I'm traveling all over the country for these Dreams shoots, meeting amazing people, and getting so much beautiful photography. I was also traveling all over to regular businesses to tell specific product stories for hardware or software tools at Square. They didn’t necessarily have big dramatic stories to them, but they were all interesting companies, and we were still taking an editorial, storytelling approach to what we were shooting. After my first six months or so at Square, I was thinking, Wow, we’ve done all this amazing work, and so much of it isn’t getting seen! Yes, some would go on our social media channels and our own website, but, for me, that didn’t seem like enough. We use the photography a ton at Square, but if you're not in the Square world, you might not be seeing it. I just thought, All this work has been made, and, in many cases, there was also copy written to go with it. It almost seems like a no-brainer to repackage it into a custom publication.

DD: How did you pitch it?

AF: Well, I pitched it a couple of times in different ways. The usual response was something like, “Yeah, a digital thing.” But I always thought it should be print, and, because everything is tested, and we can be so metrics-driven in tech, an ephemeral idea like a magazine, that is hard to test or get hard numbers on success rates, just wasn't super high priority for them.

So then my editorial sister from another mister started at Square. Chelsea Lee had been a designer at GQ. She was on another team, but we were introduced because of our shared backgrounds. Upon our first meeting, after we dished on all the magazine people we knew, I said “Hey, I have this little idea, and I don't think anyone's going to really get it until we show it to them. Do you want to partner with me, and we'll just do it on the side?” She was one hundred percent in! It was a slow and go process because we both had our very busy day jobs, but her lead saw the work she was doing on it, felt there was something there, and helped us find a stakeholder. Aaron Zamost [who recently left Square] saw the merit and was able to give us the bulk of our financial backing, as did Justin Lomax, who runs our creative team.

Cover image by Benjamin Heath
Photograph by Brent Humphreys

We were pitching it as 1000 copies for a proof-of-concept run. When Aaron bought in he asked for an extra 500 copies just for himself and his team as a leave-behind when he met with various clients and partners. (We ended up printing 5000 copies.) 

So then we had the green light, and we were full steam ahead and then we basically built a team. It's funny because Square’s not a media company, but we do have copywriters and designers, so Mallory Russell came on as the Editorial Director. She and her team went back and reported on the stories that needed to be filled out. One of our executive assistants, Emily Soffrin, became our managing editor — best one I ever had— and our production lead, Derrick Thornton, helped us get it printed. So we built this de facto masthead to make this thing but on the side of our actual jobs.

With all my publishing experience, there were still new things to figure out that I had never encountered before. What do you do when you have no ads? What do you put on the inside cover? What do you put on the back cover? How do you pace a magazine that is all spreads, no single pages?

DD: What were your criteria for the cover image? Were you using the same criteria that you used at magazines?

AF: Not really. This wasn’t going to live on a newsstand. We weren’t going to have any cover lines – or maybe just one. When we shot the cover, we were a tiny crew. I mean tiny. It was me, Chelsea, and the photographer. We didn’t even have a photo assistant with us. No groomer, no wardrobe, no location scout, no permits — run and gun to the max! I felt strongly, and the rest of the team did as well, that we didn't want this to feel like a marketing piece. The name, The Reader, is a play on the device that built Square, the “little white reader” you plug into your phone to take a credit card payment. We give a nod to it in our opening spread with our editorial letter, but The Reader could also just be the magazine you see on a coffee table that you flip through and read about interesting businesses.

DD: Were you clear on who your audience was from the beginning?

AF: I think we thought our audience would be businesses who use our products. The issue is full of great stories on how different businesses function or figure things out. Being a small business can feel lonely— you’re figuring everything out on your own. We wanted this to be a resource and a community builder for our sellers.

We also weren’t sure how Square employees would feel about it. We’re in a digital silo, and we didn’t know if this would be of value to them. Turns out they loved it. When we launched it, almost every team at the company requested issues to use with their vendors or colleagues. We even got a big thumbs up from Jack Dorsey, and that was super thrilling.

Illustration by Joseph Veazey
Photo by Peter Bohler

DD: Was it basically stories about sellers or did it also have some how-to or some instructive information?

AF: It was both. We structured it much like a regular magazine in that we had a front of the book section with shorter stories. We put a lot of service into that section. We also had some beautiful illustrations including one of a city guide that we’re hoping to do in each issue. We did some medium features and then we had a feature well with stories about businesses going cashless and a story that had never been seen by anyone about a fishing company run by women, Princess Seafood, on the northern coast of California, that had been shot by Peter Bohler.

DD: Is there a plan for another issue?

AF: We were riding high on the success of the first one, with a million plans for issue number two when the coronavirus hit. Of course, COVID has changed so many plans, but I think it’s more relevant now than ever. When have we ever been more desperate for connection and inspiration? I think all businesses want to feel they’re not alone, and, again, that sense of community is so vital now. How do I pivot? What did you do? What failed for you? How are you rebuilding? Why are you thriving and I’m sinking? We’re not just in the middle of a pandemic. We’re in the middle of social and global change. There are people losing their jobs and starting their own thing out of necessity or desire every day. I think we can make an issue so specific and helpful for our sellers but also for anyone even interested in starting a business in this moment.

DD: Did you do a digital version of that first issue as well?

AF: We did not the first time, so we're talking about that a lot. We are talking about a digital-only version for the second issue because of the pandemic. And while I don’t mind doing a digital version, I’m still beating the drum for print. Print, print, print. Print was the point all along.

The Princess Seafood feature spreads
Photos by Peter Bohler

DD: What is it about print that's so great? Why did you decide to do it for the first one?

AF: Recently I was speaking with a colleague who’s on the video team, and I was talking about the still image and how the still image lives— really in perpetuity. With video, you can add music and motion and quick cuts, and you get a sliver of something and then you move on to something else. Nothing stays on your eyeballs that long, but a photo sits there. It has so much power when you get it right. I just think that there's still something important about holding things in your hand, and, the less we do that, the more we crave it. Print is tactile, there are no banner ads or animations competing for your attention. It’s your singular experience. The paper we use is really luxe. The colors look great. You experience the stories in a different way. It all lives together in a different way. It feels like it's more meaningful because we've collected all this information and we've put it in a book and said, “Here you can have it. You can keep it.” I think when you get to hold it and experience it, it feels stronger.

DD: I feel like a lot of companies do it once and then it doesn't stick. Airbnb had Airbnb Magazine, yes, but one of the teams also did a printed publication that was for Airbnb Plus hosts. It was really beautiful, and everybody loved it, but then the second issue lost steam quickly when marketing efforts got redirected.

AF: That’s the thing I worry about. I worry about The Reader losing momentum, especially getting lost in the shuffle of all of this pandemic madness. When we started we were like, this is for Square users and for people who work at Square. But what if it just lived in a stack of magazines at a chamber of commerce? What if it was something for anyone. Isn’t it just great storytelling and great content to share? It goes beyond just the job and the hardware. It’s bigger. Princess Seafood is a David and Goliath story – a small fishing company hacking it out amongst the commercial giants, and p.s. they’re all women and they thrive because of it. Our Flint feature is saying, “Hey, we’re more than a city with bad water. We’re a vital community trying to reinvent itself.” They are all just aspirational and inspirational stories to anybody who is interested in having their own business. I think these stories are of value and that people still want to experience them in a magazine format. Am I wrong? I don't know.

DD: I think you're right. Do you ever feel troubled by that gray area of editorial mixed with marketing?

AF: I think I would if we sold it on newsstands. This feels more like a custom publication to me, like any other company would have. And we don't hit you over the head marketing Square products to you. There’s no call to sign up. It’s just storytelling. The way things were getting in journalism when I left, it didn't feel that different. Towards the end of my tenure, we were sucking up to advertisers anyway and blurring that church/state line. This actually feels more honest.

Terence Bordon
Photo by Benjamin Heath

DD: Do you think this is the next outlet for photographers who are seeing a drop off in work for traditional magazines?

AF: If we could assign original content, it could be. I don't know if that will happen. We were riding our wave of success with the first issue and then we all went inside, so I don't know. If tech at-large has the money and the desire to create print publications, it’s possible that this is where non-commercial assignment photography could move. But I think it would have to be the Apples and the Facebooks who could do it in a more general interest way. They are more of quasi-media companies anyway.

Terence Bordon

I did “assign” an original project to our staff photographer, Terence Bordon, during this time. When all the Black Lives Matter protests were happening in Oakland, all this beautiful street art went up all over downtown. He went around and photographed it, and I was just thinking, Wouldn’t it be amazing to look at double-page spreads of all this work that was made in that moment in the next issue of The Reader?

DD: And you photographed it with a certain project in mind, or you just thought you should cover it?

AF: I rarely have specific outlets attached to the things I try. If I wait for things to come to me, we miss the moment. I just…I was looking at Instagram, seeing all the protests like everybody else. We just opened a big Downtown Oakland office right where the protests were happening. The office is closed right now, of course, but I thought, All of this art has just been made around our new office. This is historic, and I don't know how long this art is going to be up. Terence was super game to do it, too. We were inspired by what was happening, and I think it’s all super relevant to Square.

DD: If you were at a different kind of company, you probably would not think, We have to get out there and shoot this.

AF: I don’t know what it would be like if I was at a different kind of company. But I do know that Jack Dorsey encourages risk-taking, encourages innovation, and encourages independent thinking. I don’t have carte blanche to do whatever I want, by any means. But I think when and where I can be smart and strategic and really draw the dotted line between my ideas and ambitions and how they relate to Square, it’s at least worth the attempt.

Lead photo by Peter Bohler.