Dear Upstatement team —

I’d love to be your new Brand Design Lead—and here’s why I think you’ll love to have me:

First: I’m a strong, seasoned manager who can be a voice for the design discipline while advocating for others—someone you can trust with taste, execution, and mentorship while you’re navigating how to bring in new business.

I empower and protect my team 💂🏻‍♂️. At Twilio I’ve turned the Creative team from a neglected service org—one that made logos bigger and reacted to last-minute requests for image assets—into a valued partner built on Trust, Service, and Integrity. I’ve improved cross-functional effectiveness with tiered SLAs, streamlined brief templates, and made creative self-serve; all of it increasing the number of projects we support by 466%.

Second: I’m a clear communicator and confident leader who can make decisions quickly (if speed is paramount), no matter the brief or audience—so you can focus on continued growth and excellence. 

I’ve made it all: multi-channel global campaigns that have delivered $2.3M in revenue, visual identity governance for teams of 70+ designers, event design for 10,000 attendees, print production that automates 3,000 sticker sheets with variable data, and stadium animations for 20,881 Chicago Bulls fans. Currently, I lead 8 designers across 15 campaigns per month and 3 web pages per week.

What’s more, I deliver pixel-perfect results—the kind that Upstatement’s clients and their customers expect and deserve 🧐. I care about integrity and details, and how they anchor successful design teams. To me, unsung work is the strongest proof of design integrity, from disciplined labeling of layers to robust internal documentation. Even when the details will never see the light of day, I’m rigorous in my principles and I get everyone on the same page about where the bar is so that we can celebrate when we cross it and make changes when we don’t.

Thanks for reading. Hopefully this gives you a sense of who I am, what’s important to me, and how we could make the world better 🌏 (each other, too).

— Sky MacFadyen


He constantly challenges everyone to ask questions which result in better, sharper work.
— Danny Sauter
I couldn’t help but be impressed with his tireless attention to detail and tenacity to create the best work possible.
— Samatha Lopez