I'm Squarespace Chief Creative Officer David Lee, And This Is How I Work

Photo: Craig Reynolds

Squarespace, in addition to funding half the podcast industry, is the standard first choice for building a professional-looking website without being a professional. We talked to one of the actual professionals, the company’s chief creative officer, about his career, his photography workflow, why he wakes up at 5:30, and how he gets his work done.


Current gig: Chief Creative Officer at Squarespace Location: New York, NY Current computer: Macbook Pro 15" Current mobile device: iPhone XS Max One word that best describes how you work: Decisive

First of all, tell us a little about your background and how you got to where you are today.

I was born in a tiny town called Saint-Foy in Quebec. At an early age, I moved to Montréal. I consider it home, as most of my childhood memories stem from my time growing up there. I was always a very visual kid, and decided to pursue an education in design. I began my professional career right as the internet boom began, when the web was a really creative medium. I then had the opportunity to transition my way into advertising, and ultimately moved to a global agency network while simultaneously running a product development company.

Squarespace has given me the opportunity to use everything I’ve learned over the course of my career and apply it to one thing that I care deeply about. I help maintain a connective thread through product design, web design, and brand marketing, and feel extremely lucky to have a job that is a true synthesis of all my past experiences.

Take us through a recent workday.

My workday starts around 9 a.m., after I walk my daughter to school. I dive right into back-to-back morning meetings. At 10 a.m., we have a weekly executive staff meeting where we talk through current business affairs at a macro and micro level. I then head into creative/marketing reviews, where we align on quarterly campaign briefs and receive feedback and approvals from our CEO.

I grab a salad from our upstairs cafeteria for early lunch around 11:30 a.m. (I skip breakfast), and catch up on emails at my desk. I then run from Tamagotchi to Game Boy, both affectionately dubbed conference rooms on the 11th floor, for 1:1 meetings with my creative production, web, brand, and product directors. I use this time to receive project updates and have open conversations with my direct reports. Then it’s off to Eminemp3 or Wiki Martin (other conference rooms) for candidate interviews.

I end my day with a budget touch base with finance, a staffing update with our HR business partner, or an internal communications strategy session. I leave the office around 6 for daddy-daughter date night at her favourite neighbourhood pizza place.

What apps, gadgets, or tools can’t you live without?

I’ve been using my iPad Pro as my main device outside of work. It has become my primary travel and entertainment device as well as my go-to workflow tool for photography. I take the photos from my camera, wifi connect it to the iPad, and bring the selects into Adobe Lightroom which I use to perfect exposure, contrast and colour. If any editing needs to be done, I’ll export out the colour corrected photos and load them into Affinity Pro (which is essentially full Photoshop for iPad). Finally, I’ll publish them onto my Squarespace site and Instagram to share.

What’s your workspace setup like?

It’s pretty uncluttered and minimal in nature. Aside from my laptop and monitor, all that’s currently on my desk is a bottle of Japanese whisky that was gifted to me.

What’s your favourite shortcut or hack?

I wake up every day at 5:30 and spend a couple of hours by myself before the family gets up. I tend to be the most alert in the morning. I’ll go for a run without music, alone with my thoughts and the sounds of the city. This is when most of my creative breakthroughs come to life. I’ll plan out my entire day and think up some of the most interesting ideas. Though it’s great physical activity, it’s more of a mental stimulus for me.

Take us through an interesting, unusual, or finicky process you have in place at work.

We are based in a 12-floor building and I have recently decided to take the stairs instead of the elevator throughout the entire work day. I’ll walk 11 flights in the morning and continually walk up and down between floors to get to my different meetings. Since my schedule is back to back, it’s been a very therapeutic way of giving myself personal time to decompress and prepare for the next meeting.

David Lee (center) with Creative Director Ben Hughes, Creative Production Director Sandra Nam, Creative Operations Management Lead Vivian Iyamba, Web Design Director Ness Higson, and Executive Assistant Valerie Gelicame (Photo: Craig Reynolds)

Who are the people who help you get things done, and how do you rely on them? 

My creative leadership team, of course. I’ve recently hired a Creative Operations Manager who has dramatically helped me. Her job is to get to know everyone on the team, and run resource management and operations. Most importantly, she listens and helps team members with career development and general happiness. I’ve also hired an executive assistant who has hit the ground running, plans my calendar, goes on missions, and helps make connections with cross-org teams.

How do you keep track of what you have to do?

Anthony Casalena, the founder and CEO of Squarespace, got me onto inbox zero, but he also made me look at email through a different lens. My inbox is now my to-do list. If there is an email sitting there, it means I have to take action on it. If I need a reminder for something, I’ll simply send myself an email so that I have a visual indicator. It’s an easy way to consolidate everything you need to do into one place.

How do you recharge or take a break?

Travel. We love to travel as a family—our five-year-old daughter has already been to India, Kenya, Morocco, Iceland, Israel, etc. We try and go to places that are so visually stunning that you won’t be compelled to check your phone.

What’s your favourite side project?

I love to photograph in my personal time. I’ve been documenting my daughter’s life since she was in the belly, and I’ve also started to publish the photography from my travels. I use a rangefinder style camera that doesn’t have autofocus, which means you have to set the aperture, shutter speed, and ISO for every shot. I’ve learned to understand lighting and exposure to the point where I can walk into any situation and know automatically what settings I need to have without flinching. It’s like learning how to drive a manual car. Once you understand how it works, you wonder why you would drive an automatic car—it just doesn’t feel like you’re driving anymore.

David’s iPad home screen (Screenshot: David Lee)

What are you currently reading, or what do you recommend?

The last book I read was 21 Lessons for the 21st Century by Yuval Noah Harrari. I read it while visiting Marrakesh, and it provided quite a contrast to what I was visually absorbing from my surroundings. It’s a masterclass sitting at the intersection of humanity and technology, and will open up your eyes to the social and political issues as a result of all this innovation. I highly recommend it.

Can you share a music playlist you’ve made?

I can’t recall the last time I made a playlist. I feel that there is simply too much music available to us today that it’s become a chore in itself to curate. I’ll pick a genre or vibe that I’m feeling and let Apple Music, Spotify or Pandora go down the rabbit hole of discovery.

Who else would you like to see answer these questions?

An old mentor of mine: Colleen Decourcy, Co-President and Chief Creative Officer at Wieden+Kennedy.

What’s the best advice you’ve ever received?

One of my old design school professors explained that drawing is not about representing what everyone else sees in front of them, it’s about finding the soul and the essence of the subject matter in your own bespoke way. He told me to try drawing with my left hand for the rest of the class.

There was an amazing childlike wonder to drawing with my off hand. It was a way to unpack and relearn how to do something that I had been doing a certain way my whole life. When I feel that I’m getting jaded or on cruise control, I use this memory as a catalyst to try new things.

What’s a problem you’re still trying to solve?

How to be more present. Technology has given us such a gift, but I don’t think humans were meant to have this many inputs. Between the work emails, slacks, news notifications, friend requests, likes and tweets etc., our brains are clogged with so much stuff that I don’t think we are remembering anything anymore. I’ve recently been trying to limit my social media so I can be more respectful of my time online. However, I’m still trying to figure out how to slow down and be more present in the moment offline.

This interview has been lightly edited.


Comments

Be the first to comment on this story!

Trending Stories Right Now